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$480,000

West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass doors opening to a screened lanai over the water, and side windows that keep natural light moving through the unit all day. Canal views extend from the main living and dining areas into the primary suite, giving the heart of the home a constant connection to the water. The primary suite features a private slider to the lanai, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. The second bedroom is a spacious ensuite with a walk-in closet. The third bedroom, with its French doors, works equally well as a guest room, home office, or flex space. The kitchen and ensuite baths feature solid wood cabinetry and granite countertops. Updated stainless steel appliances complete the kitchen. Major systems: A/C (2016), water heater (2021). Blackburn Harbor is a gated, 11-acre waterfront community with a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. No trailering, no storage hassles — just head out on the water and return to the convenience of your own dock. HOA: $980/month. Pets welcome up to 40 lbs. Minutes from Nokomis Beach, The Legacy Trail, Downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, nationally acclaimed Pine View School, and the dining and shopping along US-41 — centrally located between Sarasota and Venice. Minutes away from I-75 and the 681 connector. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.

3 Beds ⋅ 3 Baths ⋅ Blackburn Harbor Waterfront Villas SubDv. ⋅ 34229 Zip Code

West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass doors opening to a screened lanai over the water, and side windows that keep natural light moving through the unit all day. Canal views extend from the main living and dining areas into the primary suite, giving the heart of the home a constant connection to the water. The primary suite features a private slider to the lanai, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. The second bedroom is a spacious ensuite with a walk-in closet. The third bedroom, with its French doors, works equally well as a guest room, home office, or flex space. The kitchen and ensuite baths feature solid wood cabinetry and granite countertops. Updated stainless steel appliances complete the kitchen. Major systems: A/C (2016), water heater (2021). Blackburn Harbor is a gated, 11-acre waterfront community with a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. No trailering, no storage hassles — just head out on the water and return to the convenience of your own dock. HOA: $980/month. Pets welcome up to 40 lbs. Minutes from Nokomis Beach, The Legacy Trail, Downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, nationally acclaimed Pine View School, and the dining and shopping along US-41 — centrally located between Sarasota and Venice. Minutes away from I-75 and the 681 connector. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.

2309 Jessie Harbor Drive Unit 2402, Osprey

$317,000

"Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. The attached ground-level garage beneath the residence offers convenience when arriving or heading out. The open-concept layout floor plan, soaring ceilings, and split-bedroom layout create perfect privacy. Stunning chef’s kitchen, granite countertops, stainless steel appliances, and a center island with seating, walk-in pantry, and upgraded fixtures. The primary suite features a walk-in closet, a spa, a double vanity, and a walk-in shower. Two other bedrooms on the opposite side, along with a second full bathroom, gives comfort and privacy for families or guests. Relax on the screened-in lanai overlooking beautiful water views for morning coffee or evening cocktails. The Tesla charger installed in the garage is a bonus. The community is located in a prime location with quick access to US-41, I-75, Siesta Key Beach, and Nokomis Beach, Bay Street Park with its playground and dog park, and walking distance to renowned Pine View School, Walmart, and the Legacy Trail. Bay Street Village resort-style amenities include a heated pool, fitness center, and clubhouse. The monthly condo fee covering exterior maintenance, roof, water, sewer, and two gated entrances… Don’t miss this rare opportunity – call the listing agent now to schedule a private viewing.

3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

"Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. The attached ground-level garage beneath the residence offers convenience when arriving or heading out. The open-concept layout floor plan, soaring ceilings, and split-bedroom layout create perfect privacy. Stunning chef’s kitchen, granite countertops, stainless steel appliances, and a center island with seating, walk-in pantry, and upgraded fixtures. The primary suite features a walk-in closet, a spa, a double vanity, and a walk-in shower. Two other bedrooms on the opposite side, along with a second full bathroom, gives comfort and privacy for families or guests. Relax on the screened-in lanai overlooking beautiful water views for morning coffee or evening cocktails. The Tesla charger installed in the garage is a bonus. The community is located in a prime location with quick access to US-41, I-75, Siesta Key Beach, and Nokomis Beach, Bay Street Park with its playground and dog park, and walking distance to renowned Pine View School, Walmart, and the Legacy Trail. Bay Street Village resort-style amenities include a heated pool, fitness center, and clubhouse. The monthly condo fee covering exterior maintenance, roof, water, sewer, and two gated entrances… Don’t miss this rare opportunity – call the listing agent now to schedule a private viewing.

4213 Expedition Way Unit 107, Osprey

$825,000

Build your dream home in one of Osprey's most exclusive waterfront communities. Nestled on a premium cul-de-sac homesite in the private enclave of Parrot Bay, this exceptional property is one of only nine custom home sites, offering a rare opportunity to create a truly personalized coastal retreat with the builder of your choice. Included in the sale is a private boat dock that accommodates up to a 30-foot vessel, providing easy access to the Intracoastal Waterway and the Gulf of Mexico. Whether you enjoy boating, fishing, or simply watching the sunset from the water, this property offers the ultimate Florida waterfront lifestyle. Parrot Bay is a boutique community designed for privacy and relaxation, complete with a community pickleball court and beautifully maintained surroundings. Ideally located between Sarasota and Venice, you're just minutes from Nokomis Beach, Siesta Key, Casey Key, waterfront dining, shopping, golf, and the area's best parks and attractions. Opportunities to purchase a homesite with an included boat dock in a community this small and desirable are incredibly rare. Don't miss your chance to build the custom waterfront home you've always envisioned in one of Osprey's most sought-after locations.

Osprey Avenue Sub SubDv. ⋅ 34229 Zip Code

Build your dream home in one of Osprey's most exclusive waterfront communities. Nestled on a premium cul-de-sac homesite in the private enclave of Parrot Bay, this exceptional property is one of only nine custom home sites, offering a rare opportunity to create a truly personalized coastal retreat with the builder of your choice. Included in the sale is a private boat dock that accommodates up to a 30-foot vessel, providing easy access to the Intracoastal Waterway and the Gulf of Mexico. Whether you enjoy boating, fishing, or simply watching the sunset from the water, this property offers the ultimate Florida waterfront lifestyle. Parrot Bay is a boutique community designed for privacy and relaxation, complete with a community pickleball court and beautifully maintained surroundings. Ideally located between Sarasota and Venice, you're just minutes from Nokomis Beach, Siesta Key, Casey Key, waterfront dining, shopping, golf, and the area's best parks and attractions. Opportunities to purchase a homesite with an included boat dock in a community this small and desirable are incredibly rare. Don't miss your chance to build the custom waterfront home you've always envisioned in one of Osprey's most sought-after locations.

3820 Parrot Bay Court, Osprey

$760,000

Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool table. Dining room offers a built in bar area. Nicely equipped cherry kitchen opens to family room with fireplace and sliding glass doors onto the courtyard. Travertine floors are also in the diningroom, kitchen and family room. The primary suite is located on one side of the home while the other two bedrooms are on the other side. The primary suite also looks onto the pool area. The large courtyard offers plenty of covered space for lounging plus solar heated pool, and an above ground hot tub! All furniture can be left with the home and is negotiable if you are looking to move right in and start enjoying the fabulous Florida lifestyle. OTHER BENEFITS OF THE HOME INCLUDE RECENTLY REPLACED A/C, A GENERATOR, ROOF APROX. 13 YEARS OLD, POOL RESURFACED IN 2009. Speaking of lifestyle…there is none finer than living in Southbay! The marina which is exclusive to Southbay residents offers low dock lease fees. Renovated club house has much to offer including a ballroom, casual “livingroom” areas, two kitchens, fitness center, card room, library, community pool, pickleball courts, tennis courts and activities galore! Picturesque views, walking trails, kayak launch, kayak storage, playground, bocce ball court and more. Come explore Southbay, you won’t be disappointed!

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool table. Dining room offers a built in bar area. Nicely equipped cherry kitchen opens to family room with fireplace and sliding glass doors onto the courtyard. Travertine floors are also in the diningroom, kitchen and family room. The primary suite is located on one side of the home while the other two bedrooms are on the other side. The primary suite also looks onto the pool area. The large courtyard offers plenty of covered space for lounging plus solar heated pool, and an above ground hot tub! All furniture can be left with the home and is negotiable if you are looking to move right in and start enjoying the fabulous Florida lifestyle. OTHER BENEFITS OF THE HOME INCLUDE RECENTLY REPLACED A/C, A GENERATOR, ROOF APROX. 13 YEARS OLD, POOL RESURFACED IN 2009. Speaking of lifestyle…there is none finer than living in Southbay! The marina which is exclusive to Southbay residents offers low dock lease fees. Renovated club house has much to offer including a ballroom, casual “livingroom” areas, two kitchens, fitness center, card room, library, community pool, pickleball courts, tennis courts and activities galore! Picturesque views, walking trails, kayak launch, kayak storage, playground, bocce ball court and more. Come explore Southbay, you won’t be disappointed!

1495 Landview Lane, Osprey

$1,770,000

Imagine starting your morning with coffee beside your private courtyard pool, opening the sliders to the Florida sunshine and ending the day with friends gathered around the kitchen island before heading out by golf cart for dinner or a sunset near the water. Welcome to 206 Four Knot Lane, a beautifully updated, move-in-ready home in Southbay Yacht & Racquet Club, one of Osprey’s most desirable waterfront marina communities. At the heart of the home is an impressive 14' x 37' heated pool, framed on three sides by the residence and visible from multiple living spaces. Several rooms open directly to the covered lanais and pool area, creating a private courtyard-style setting and a seamless connection between indoor and outdoor living. Inside, the 2,411-square-foot residence offers 3 bedrooms, 2 baths, an office/den, spacious living areas, and a thoughtfully designed split floor plan. Floor-to-ceiling impact-rated windows and sliders installed in 2020 fill the home with natural light and showcase the pool from throughout the main living spaces. The primary suite is privately positioned and includes an adjoining office/den and ensuite bath with soaking tub and custom cabinetry. Two additional bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed provides added flexibility for overnight guests or workspace. The home has been extensively updated with 12" x 72" Ceramica Sant’Agostino Italian porcelain plank tile flooring in Barkwood Ash, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint completed in 2025. The chef-inspired kitchen is designed for both everyday living and entertaining, with new custom cabinetry, quartz countertops, high-end 2025 GE Monogram appliances, a 48-inch refrigerator, induction cooktop, wall oven/microwave, built-in wine refrigerator, excellent storage, and a large center island with seating for 8–10. The adjoining dining area features an integrated bar with custom cabinetry and a fireplace ready for an insert. Additional highlights include dual-zone A/C systems installed in 2025, new Electrolux stackable washer and dryer, a spacious laundry room with utility sink and coffee/tea bar, concrete tile roof installed in 2020, re-plumbing completed in 2007, an oversized 2-car garage with epoxy flooring and custom storage, mature tropical landscaping with irrigation, and a private outdoor shower. There is also potential to add a fourth bedroom with ensuite bath or create additional garage/storage space. Southbay Yacht & Racquet Club offers a true Florida lifestyle with a private 172-slip deep-water marina accommodating vessels up to approximately 58 feet, along with a clubhouse, fitness center, heated community pool and spa, tennis, pickleball, basketball, bocce, playground, kayak launch and storage, jet ski pads, low HOA fees, and an active social atmosphere. The golf-cart-friendly community provides convenient access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, tiki bars, and everything that makes Florida’s Gulf Coast lifestyle so appealing. Interior and exterior furnishings, artwork, televisions, potted plants, outdoor gas grill, and pizza oven are available separately by bill of sale. If you have been searching for a beautifully updated home where the pool, the home, the marina, and the Florida lifestyle all come together, 206 Four Knot Lane deserves to be seen in person.

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Imagine starting your morning with coffee beside your private courtyard pool, opening the sliders to the Florida sunshine and ending the day with friends gathered around the kitchen island before heading out by golf cart for dinner or a sunset near the water. Welcome to 206 Four Knot Lane, a beautifully updated, move-in-ready home in Southbay Yacht & Racquet Club, one of Osprey’s most desirable waterfront marina communities. At the heart of the home is an impressive 14' x 37' heated pool, framed on three sides by the residence and visible from multiple living spaces. Several rooms open directly to the covered lanais and pool area, creating a private courtyard-style setting and a seamless connection between indoor and outdoor living. Inside, the 2,411-square-foot residence offers 3 bedrooms, 2 baths, an office/den, spacious living areas, and a thoughtfully designed split floor plan. Floor-to-ceiling impact-rated windows and sliders installed in 2020 fill the home with natural light and showcase the pool from throughout the main living spaces. The primary suite is privately positioned and includes an adjoining office/den and ensuite bath with soaking tub and custom cabinetry. Two additional bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed provides added flexibility for overnight guests or workspace. The home has been extensively updated with 12" x 72" Ceramica Sant’Agostino Italian porcelain plank tile flooring in Barkwood Ash, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint completed in 2025. The chef-inspired kitchen is designed for both everyday living and entertaining, with new custom cabinetry, quartz countertops, high-end 2025 GE Monogram appliances, a 48-inch refrigerator, induction cooktop, wall oven/microwave, built-in wine refrigerator, excellent storage, and a large center island with seating for 8–10. The adjoining dining area features an integrated bar with custom cabinetry and a fireplace ready for an insert. Additional highlights include dual-zone A/C systems installed in 2025, new Electrolux stackable washer and dryer, a spacious laundry room with utility sink and coffee/tea bar, concrete tile roof installed in 2020, re-plumbing completed in 2007, an oversized 2-car garage with epoxy flooring and custom storage, mature tropical landscaping with irrigation, and a private outdoor shower. There is also potential to add a fourth bedroom with ensuite bath or create additional garage/storage space. Southbay Yacht & Racquet Club offers a true Florida lifestyle with a private 172-slip deep-water marina accommodating vessels up to approximately 58 feet, along with a clubhouse, fitness center, heated community pool and spa, tennis, pickleball, basketball, bocce, playground, kayak launch and storage, jet ski pads, low HOA fees, and an active social atmosphere. The golf-cart-friendly community provides convenient access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, tiki bars, and everything that makes Florida’s Gulf Coast lifestyle so appealing. Interior and exterior furnishings, artwork, televisions, potted plants, outdoor gas grill, and pizza oven are available separately by bill of sale. If you have been searching for a beautifully updated home where the pool, the home, the marina, and the Florida lifestyle all come together, 206 Four Knot Lane deserves to be seen in person.

206 Four Knot Lane, Osprey

$89,000

Extra-wide indoor boat rack accommodating vessels up to 33' L x 11.1' W x 9.3' H, with quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash service, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Condo fees cover in and outs, insurance, marina and building maintenance, staff, and equipment. Indoor storage offers year-round peace of mind and protection from the elements, while rental potential may make this an excellent Sarasota waterfront investment opportunity. Buyer to verify vessel fit and rental rules with the marina/association.

Dry Slips At Bellagio Village SubDv. ⋅ 34229 Zip Code

Extra-wide indoor boat rack accommodating vessels up to 33' L x 11.1' W x 9.3' H, with quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash service, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Condo fees cover in and outs, insurance, marina and building maintenance, staff, and equipment. Indoor storage offers year-round peace of mind and protection from the elements, while rental potential may make this an excellent Sarasota waterfront investment opportunity. Buyer to verify vessel fit and rental rules with the marina/association.

570 Blackburn Point Road Unit 23, Osprey

$415,000

Studio E3 at Osprey Executive Park is a fully renovated executive suite built for businesses that take their image seriously. Step into the reception area and you're greeted by a stone accent wall and fireplace a combination that feels warm without losing its polish. Designer tile runs throughout the suite, tying the space together and setting the tone before a single meeting starts. The layout includes three private offices and a generous conference room, each fronted with glass doors that keep the space feeling open while still giving your team the privacy they need. It's a floor plan that works equally well for client meetings, team collaboration, or quiet, focused work. The kitchen is where the suite really shows its quality soft-close wood cabinetry, marble countertops, and a stone backsplash that wouldn't look out of place in a high-end home. Even the restroom carries the same attention to detail, with a full-length vanity and finishes to match the rest of the space. Two separate storage rooms round things out, giving you somewhere to keep files, supplies, and equipment without cluttering the work areas. This isn't just office space it's a setting that tells clients something about who you are before you say a word.

Osprey Executive Park SubDv. ⋅ 34229 Zip Code

Studio E3 at Osprey Executive Park is a fully renovated executive suite built for businesses that take their image seriously. Step into the reception area and you're greeted by a stone accent wall and fireplace a combination that feels warm without losing its polish. Designer tile runs throughout the suite, tying the space together and setting the tone before a single meeting starts. The layout includes three private offices and a generous conference room, each fronted with glass doors that keep the space feeling open while still giving your team the privacy they need. It's a floor plan that works equally well for client meetings, team collaboration, or quiet, focused work. The kitchen is where the suite really shows its quality soft-close wood cabinetry, marble countertops, and a stone backsplash that wouldn't look out of place in a high-end home. Even the restroom carries the same attention to detail, with a full-length vanity and finishes to match the rest of the space. Two separate storage rooms round things out, giving you somewhere to keep files, supplies, and equipment without cluttering the work areas. This isn't just office space it's a setting that tells clients something about who you are before you say a word.

418 S Tamiami Trail Unit E3, Osprey

$395,000

**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey

$575,000

One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities. Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always envisioned. Bring your own builder and architect and create a residence tailored to your lifestyle, surrounded by majestic oak trees, winding streets, and distinctive estate homes. The Oaks Bayside is renowned for its peaceful Old Florida charm, mature landscaping, and prime location along Little Sarasota Bay. This sought-after neighborhood offers a unique blend of privacy, natural beauty, and convenience, just minutes from the beaches of Casey Key, downtown Sarasota, and the area's finest shopping, dining, and cultural attractions. Ownership includes membership in The Oaks Club, one of Florida's most respected private club communities, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, croquet, a state-of-the-art WellFit Center, Junior Olympic heated swimming pool, bocce, basketball, playground facilities, multiple dining venues, and a vibrant year-round social calendar. Club membership is required, and there is currently NO WAITING LIST for either Golf or Sports/Social membership.

Oaks SubDv. ⋅ 34229 Zip Code

One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities. Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always envisioned. Bring your own builder and architect and create a residence tailored to your lifestyle, surrounded by majestic oak trees, winding streets, and distinctive estate homes. The Oaks Bayside is renowned for its peaceful Old Florida charm, mature landscaping, and prime location along Little Sarasota Bay. This sought-after neighborhood offers a unique blend of privacy, natural beauty, and convenience, just minutes from the beaches of Casey Key, downtown Sarasota, and the area's finest shopping, dining, and cultural attractions. Ownership includes membership in The Oaks Club, one of Florida's most respected private club communities, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, croquet, a state-of-the-art WellFit Center, Junior Olympic heated swimming pool, bocce, basketball, playground facilities, multiple dining venues, and a vibrant year-round social calendar. Club membership is required, and there is currently NO WAITING LIST for either Golf or Sports/Social membership.

143 Osprey Point Drive, Osprey

$249,900

Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such as cabinetry and showers. Enjoy the spacious rooms with the master bedroom having a walk in closet plus another closet. Each bedroom features its own small balcony - perfect for your morning coffee. The lanai off the livingroom will become a focal point for easy living offering a private wooded back yard area. Kitchen features white cabinets with quartz countertops, tile backsplash and stainless steel appliances. A carport plus two exterior storage closets are also nice benefits. The Pine Run neighborhood is an active community offering many activities including pickleball and tennis. There are two pools - the main pool by the club house and fitness center offers gas grills and a scenic view. The second pool is just a short walk from this condo. Kayak storage is available in the neighborhood with a boat and kayak launch just up the street at the Blackburn Point park. This location offers the best of everything. Located between Sarasota and Venice, you are within easy reach of both. Nokomis Beach is 5 miles away, Siesta Key Beach is 9 miles away! The intracoastal waterway is just up the road leading to the ever popular Casey Key Fish House and Tiki Bar. Many other restaurants, shopping and major roads are close at hand. Come see for yourself what makes this condo and Pine Run so special!

2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code

Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such as cabinetry and showers. Enjoy the spacious rooms with the master bedroom having a walk in closet plus another closet. Each bedroom features its own small balcony - perfect for your morning coffee. The lanai off the livingroom will become a focal point for easy living offering a private wooded back yard area. Kitchen features white cabinets with quartz countertops, tile backsplash and stainless steel appliances. A carport plus two exterior storage closets are also nice benefits. The Pine Run neighborhood is an active community offering many activities including pickleball and tennis. There are two pools - the main pool by the club house and fitness center offers gas grills and a scenic view. The second pool is just a short walk from this condo. Kayak storage is available in the neighborhood with a boat and kayak launch just up the street at the Blackburn Point park. This location offers the best of everything. Located between Sarasota and Venice, you are within easy reach of both. Nokomis Beach is 5 miles away, Siesta Key Beach is 9 miles away! The intracoastal waterway is just up the road leading to the ever popular Casey Key Fish House and Tiki Bar. Many other restaurants, shopping and major roads are close at hand. Come see for yourself what makes this condo and Pine Run so special!

116 Woodland Place Unit 116, Osprey

$1,595,000

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey

$1,495,000

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey

$695,000

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural beauty and impressive estate homes. The Oaks Bayside is treasured for its peaceful, Old Florida character, with a neighborhood setting along Little Sarasota Bay and beautifully landscaped streets that reflect the elegance and privacy of this exclusive community. Design your dream home in a tranquil environment while enjoying access to the exceptional lifestyle The Oaks is known for. Club amenities include three restaurants, a ballroom, two 18-hole championship golf courses, award-winning racquet programs with 12 Har-Tru hydro-grid tennis courts, four pickleball courts, official croquet green, state-of-the-art fitness center, Junior Olympic heated community pool, bocce, basketball court and playground. The Oaks has earned recognition as a Platinum Club of America, Emerald Club of the World, Distinguished Club of the World and one of America’s Healthiest Clubs. Ideally near nationally ranked Pine View School, the Legacy Trail, world-famous Siesta Key, shopping, dining, cultural venues, entertainment and Gulf Coast beaches, this exceptional homesite offers a rare opportunity to enjoy privacy, prestige and the full country club lifestyle in one of Sarasota’s premier gated communities.

Oaks The SubDv. ⋅ 34229 Zip Code

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural beauty and impressive estate homes. The Oaks Bayside is treasured for its peaceful, Old Florida character, with a neighborhood setting along Little Sarasota Bay and beautifully landscaped streets that reflect the elegance and privacy of this exclusive community. Design your dream home in a tranquil environment while enjoying access to the exceptional lifestyle The Oaks is known for. Club amenities include three restaurants, a ballroom, two 18-hole championship golf courses, award-winning racquet programs with 12 Har-Tru hydro-grid tennis courts, four pickleball courts, official croquet green, state-of-the-art fitness center, Junior Olympic heated community pool, bocce, basketball court and playground. The Oaks has earned recognition as a Platinum Club of America, Emerald Club of the World, Distinguished Club of the World and one of America’s Healthiest Clubs. Ideally near nationally ranked Pine View School, the Legacy Trail, world-famous Siesta Key, shopping, dining, cultural venues, entertainment and Gulf Coast beaches, this exceptional homesite offers a rare opportunity to enjoy privacy, prestige and the full country club lifestyle in one of Sarasota’s premier gated communities.

216 Osprey Point Drive, Osprey

$299,990

Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining beautiful kitchen with center island, walk-in pantry and stainless steel appliances. The primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Bay Street offers easy access to Nokomis Beach and the world-famous Siesta Key Beach. Close to shopping and restaurants.

2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining beautiful kitchen with center island, walk-in pantry and stainless steel appliances. The primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Bay Street offers easy access to Nokomis Beach and the world-famous Siesta Key Beach. Close to shopping and restaurants.

4296 Expedition Way Unit 104, Osprey

$4,790,000

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey

$749,000

**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

103 Bishops Court Road, Osprey

$185,000

Virtually Staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and lighting. The possibilities are endless as this space can be kept for leisure or used to build an additional home. The seller invested $28,000 in fundamental upgrades, includin g: New subflooring and moisture barrier, Laminate flooring throughout main living areas and bathrooms, and Fresh carpeting in bedrooms and the Florida Room. The interior features an open floor plan with two bedrooms. The primary suite includes dual walk-in closets and a ensuite bath. This home is light and bright with a comfortable Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage and includes a washer and dryer. This desirable lot is located in the pet-friendly section of the park. Monthly dues include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, sewer, cable TV, and internet. The Seller recently spent $28,000 on a new sub floor, new moisture barrier, New laminate flooring in kitchen, dining, great room, bathrooms, and hallway. New carpet in both bedrooms and Florida room. There’s even an on-site storage area for your boats, RVs, or kayaks for a small fee! The location is unbeatable—close to Casey Key, the Legacy Trail, Walmart, shopping, restaurants and the Nokomis and Siesta Key Beaches. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, heated pool, dog run, shuffleboard, exercise area, and regular social events.

2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code

Virtually Staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and lighting. The possibilities are endless as this space can be kept for leisure or used to build an additional home. The seller invested $28,000 in fundamental upgrades, includin g: New subflooring and moisture barrier, Laminate flooring throughout main living areas and bathrooms, and Fresh carpeting in bedrooms and the Florida Room. The interior features an open floor plan with two bedrooms. The primary suite includes dual walk-in closets and a ensuite bath. This home is light and bright with a comfortable Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage and includes a washer and dryer. This desirable lot is located in the pet-friendly section of the park. Monthly dues include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, sewer, cable TV, and internet. The Seller recently spent $28,000 on a new sub floor, new moisture barrier, New laminate flooring in kitchen, dining, great room, bathrooms, and hallway. New carpet in both bedrooms and Florida room. There’s even an on-site storage area for your boats, RVs, or kayaks for a small fee! The location is unbeatable—close to Casey Key, the Legacy Trail, Walmart, shopping, restaurants and the Nokomis and Siesta Key Beaches. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, heated pool, dog run, shuffleboard, exercise area, and regular social events.

320 Tropic Drive, Osprey

$719,000

Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.

3 Beds ⋅ 2 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code

Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.

280 Hidden Bay Drive Unit 302, Osprey

$1,289,000

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless luxury residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac in Bishops Court, an intimate gated enclave within The Oaks Preserve in Osprey, Florida. Framed by lush conservation views and a canopy of mature oaks, the property blends classic architectural character with thoughtfully curated updates in one of the Sarasota area’s most prestigious private country club communities. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living areas, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen. Custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting define the space. A Sonos sound system extends throughout the residence. The primary suite is a private retreat featuring vaulted ceilings, a bay-window sitting area, outdoor access, and a fully renovated, spa-inspired bathroom completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. The additional bathrooms have also been extensively renovated with elevated finishes and designer fixtures. In the laundry room, custom storage, shiplap detailing, and functional built-ins boast a refined aesthetic. Upstairs, a spacious bonus room, freshly painted in 2026, features a fireplace and opens directly to a newly renovated second-story deck overlooking the treetops. Complete with a full bathroom, this highly versatile level can serve as private guest accommodations, a recreation or media room, home office, art studio, creative retreat, or secluded lounge. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and peaceful preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor; new lanai screening and aluminum framing; exterior paint completed in 2025; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club. The Oaks offers an exceptional club-centered lifestyle just south of Sarasota, with two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active year-round social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has earned recognition as a Platinum Club of America, a Distinguished Emerald Residential Country Club, and an Audubon International Certified property, reinforcing its standing as a premier private residential club. The Oaks delivers an exceptional lifestyle in Osprey between Sarasota and Venice. Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota, and historic Venice are all within easy reach.

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless luxury residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac in Bishops Court, an intimate gated enclave within The Oaks Preserve in Osprey, Florida. Framed by lush conservation views and a canopy of mature oaks, the property blends classic architectural character with thoughtfully curated updates in one of the Sarasota area’s most prestigious private country club communities. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living areas, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen. Custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting define the space. A Sonos sound system extends throughout the residence. The primary suite is a private retreat featuring vaulted ceilings, a bay-window sitting area, outdoor access, and a fully renovated, spa-inspired bathroom completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. The additional bathrooms have also been extensively renovated with elevated finishes and designer fixtures. In the laundry room, custom storage, shiplap detailing, and functional built-ins boast a refined aesthetic. Upstairs, a spacious bonus room, freshly painted in 2026, features a fireplace and opens directly to a newly renovated second-story deck overlooking the treetops. Complete with a full bathroom, this highly versatile level can serve as private guest accommodations, a recreation or media room, home office, art studio, creative retreat, or secluded lounge. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and peaceful preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor; new lanai screening and aluminum framing; exterior paint completed in 2025; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club. The Oaks offers an exceptional club-centered lifestyle just south of Sarasota, with two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active year-round social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has earned recognition as a Platinum Club of America, a Distinguished Emerald Residential Country Club, and an Audubon International Certified property, reinforcing its standing as a premier private residential club. The Oaks delivers an exceptional lifestyle in Osprey between Sarasota and Venice. Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota, and historic Venice are all within easy reach.

156 Bishops Court Road, Osprey

$275,000

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

1 Beds ⋅ 1 Baths ⋅ Windsor Lodge At The Oaks SubDv. ⋅ 34229 Zip Code

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

51 Macewen Drive Unit 12, Osprey

$3,295,000

**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid concrete block construction on both levels and encompassing 6,254 sq ft under roof, this residence is designed for durability and peace of mind. The elevated main living level at an 18 ft elevation, features Double-insulated Hurricane-Impact windows and sliding doors on the main level, hurricane impact windows on the lower level, and wraparound balconies with a private lanai to take in sunrise and sunset views. The open-concept interior is designed for comfort and entertaining, highlighted by 14 ft coffered ceilings, crown molding, custom built-ins, LED lighting, and abundant natural light. The kitchen is beautifully appointed with a large granite island, generous counter space, and a gallery window framing the water. The home offers 3 Bedrooms (all En Suite), 3 Full and 1 Half Baths on main level and an additional Full Bath on the lower level. The spacious primary suite includes balcony access, three custom closets, and a spa-style bath with dual vanities, makeup counter, jetted tub, and oversized tiled shower. The lower level entails an additional nonconforming bedroom, bathroom and recreation room with access to outdoor patio. 4-Car Garage plus extensive space for storage and recreational equipment. Construction features include energy-efficient closed-cell insulation, interior metal framing, Hardie/cement board on lower level, concrete stairway, elevator shaft (currently used as a safe room), freshly painted exterior. Enjoy the large paved patio with ample room to add a Pool. Ideally located near world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School.

3 Beds ⋅ 5 Baths ⋅ Sorrento Shores SubDv. ⋅ 34229 Zip Code

**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid concrete block construction on both levels and encompassing 6,254 sq ft under roof, this residence is designed for durability and peace of mind. The elevated main living level at an 18 ft elevation, features Double-insulated Hurricane-Impact windows and sliding doors on the main level, hurricane impact windows on the lower level, and wraparound balconies with a private lanai to take in sunrise and sunset views. The open-concept interior is designed for comfort and entertaining, highlighted by 14 ft coffered ceilings, crown molding, custom built-ins, LED lighting, and abundant natural light. The kitchen is beautifully appointed with a large granite island, generous counter space, and a gallery window framing the water. The home offers 3 Bedrooms (all En Suite), 3 Full and 1 Half Baths on main level and an additional Full Bath on the lower level. The spacious primary suite includes balcony access, three custom closets, and a spa-style bath with dual vanities, makeup counter, jetted tub, and oversized tiled shower. The lower level entails an additional nonconforming bedroom, bathroom and recreation room with access to outdoor patio. 4-Car Garage plus extensive space for storage and recreational equipment. Construction features include energy-efficient closed-cell insulation, interior metal framing, Hardie/cement board on lower level, concrete stairway, elevator shaft (currently used as a safe room), freshly painted exterior. Enjoy the large paved patio with ample room to add a Pool. Ideally located near world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School.

135 Tina Island Drive, Osprey

$284,900

Luxury Corner Residence in Osprey | Top-Rated Pine View School District. Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities. This FULLY FURNISHED 2-bedroom, 2-bathroom home with a private garage showcases light-filled, open-concept interiors, enhanced by hurricane-impact windows and elegant finishes throughout. The spacious layout is designed for both comfort and entertaining, featuring an oversized kitchen island, stainless steel appliances, and generous storage. Step outside to your private screened lanai, perfect for relaxing mornings or unwinding in the evening in a peaceful, tropical setting. Highlights include: Highly sought-after corner unit for added privacy and natural light Private garage + additional parking Resort-style community with pool Pet-friendly neighborhood Meticulously maintained, move-in ready condition Ideally located just minutes from Siesta Key Beach, Nokomis Beach, dining, shopping, and the Legacy Trail, this property also offers proximity to the nationally recognized Pine View School, consistently ranked among the top public schools in Florida. Whether you are looking for a primary residence, seasonal retreat, or investment property, this home delivers both lifestyle and long-term value. Luxury, location, and top-tier education—this is Osprey living at its finest.

2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

Luxury Corner Residence in Osprey | Top-Rated Pine View School District. Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities. This FULLY FURNISHED 2-bedroom, 2-bathroom home with a private garage showcases light-filled, open-concept interiors, enhanced by hurricane-impact windows and elegant finishes throughout. The spacious layout is designed for both comfort and entertaining, featuring an oversized kitchen island, stainless steel appliances, and generous storage. Step outside to your private screened lanai, perfect for relaxing mornings or unwinding in the evening in a peaceful, tropical setting. Highlights include: Highly sought-after corner unit for added privacy and natural light Private garage + additional parking Resort-style community with pool Pet-friendly neighborhood Meticulously maintained, move-in ready condition Ideally located just minutes from Siesta Key Beach, Nokomis Beach, dining, shopping, and the Legacy Trail, this property also offers proximity to the nationally recognized Pine View School, consistently ranked among the top public schools in Florida. Whether you are looking for a primary residence, seasonal retreat, or investment property, this home delivers both lifestyle and long-term value. Luxury, location, and top-tier education—this is Osprey living at its finest.

184 Explorer Drive, Osprey

$798,000

One or more photo(s) has been virtually staged. PRICE IMPROVED OVER $50K!!!! Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.

3 Beds ⋅ 4 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. PRICE IMPROVED OVER $50K!!!! Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.

6100 Jessie Harbor Drive Unit 202, Osprey

$1,950,000

Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

97 Sugar Mill Drive, Osprey

$510,000

Virtually Staged. SPACIOUS 2,000+ SQ FT HOME, UPDATED BEDROOM FLOORING, PRIVATE BACKYARD, COVERED LANAI & 2-CAR GARAGE in The Palms of Casey Key, offering a comfortable layout designed for both everyday living and entertaining. The inviting interior features UPDATED FLOORING THROUGHOUT THE BEDROOMS & CLOSETS with durable tile in the main living areas for easy maintenance. A spacious great room provides plenty of room to gather, while the private primary suite is tucked away at the rear and features DUAL SINKS, SOAKING TUB, WALK-IN SHOWER & GENEROUS CLOSET SPACE. Step outside to the COVERED LANAI & PRIVATE BACKYARD, perfect for enjoying your morning coffee or hosting friends and family. Additional highlights include a 2-CAR GARAGE and a well-maintained community with HOA oversight and nearby amenities. Located JUST STEPS FROM PINE VIEW SCHOOL with easy access to US-41 and I-75, this home puts TOP-RATED SCHOOLS, BEACHES, MARINAS, DINING & SHOPPING within minutes.

3 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code

Virtually Staged. SPACIOUS 2,000+ SQ FT HOME, UPDATED BEDROOM FLOORING, PRIVATE BACKYARD, COVERED LANAI & 2-CAR GARAGE in The Palms of Casey Key, offering a comfortable layout designed for both everyday living and entertaining. The inviting interior features UPDATED FLOORING THROUGHOUT THE BEDROOMS & CLOSETS with durable tile in the main living areas for easy maintenance. A spacious great room provides plenty of room to gather, while the private primary suite is tucked away at the rear and features DUAL SINKS, SOAKING TUB, WALK-IN SHOWER & GENEROUS CLOSET SPACE. Step outside to the COVERED LANAI & PRIVATE BACKYARD, perfect for enjoying your morning coffee or hosting friends and family. Additional highlights include a 2-CAR GARAGE and a well-maintained community with HOA oversight and nearby amenities. Located JUST STEPS FROM PINE VIEW SCHOOL with easy access to US-41 and I-75, this home puts TOP-RATED SCHOOLS, BEACHES, MARINAS, DINING & SHOPPING within minutes.

4429 Conchfish Lane, Osprey

$999,900

This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. Arrive in effortless luxury with an elevator that opens directly into this beautifully appointed condo, creating an exceptional sense of privacy and exclusivity. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code

This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. Arrive in effortless luxury with an elevator that opens directly into this beautifully appointed condo, creating an exceptional sense of privacy and exclusivity. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!

14021 Bellagio Way Unit 404, Osprey

$560,000

Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. There is currently no waiting list for either Golf or Sports/Social membership.

3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. There is currently no waiting list for either Golf or Sports/Social membership.

409 North Point Road Unit 401, Osprey

$285,000

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey

$235,000

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey

$700,000

Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms

4 Beds ⋅ 4 Baths ⋅ Rivendell The Woodlands SubDv. ⋅ 34229 Zip Code

Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms

759 Fordingbridge Way, Osprey