Orange County Market Snapshot: Active Listings
Across all of Orange County, there are 3,525 active residential listings right now:
- 3,525 total active homes currently on the market in Orange County
- Average list price of $877,819, reflecting Orlando's mix of everyday family neighborhoods alongside high-end lakefront communities like Windermere and Isleworth
- Average cost per square foot of $309 across all active inventory
- 1,509 homes are under contract countywide (about 43% of active inventory), averaging $714,362 at $279/sq ft, with a shorter average pending timeline of 57 days
- 6,342 homes have sold in the past 6 months at an average sold price of $669,423 — about 97.1% of average list price, and averaging just 52 days on market
City Spotlight: Winter Park, Windermere & Winter Garden
County-wide averages only tell part of the story in a market this varied. Here's how three of Orange County's most-searched suburbs compare right now, including how they're actually closing — not just listing:
Winter Park 201 active
Winter Park's established, tree-lined neighborhoods command the highest cost per square foot of the three spotlighted cities at $495. Homes sold in the past 6 months averaged $1,083,703 against a $1,119,234 average list price — a sale-to-list ratio of about 96.8%, reflecting steady demand for this classic Orlando suburb.
Windermere 195 active
Windermere carries by far the highest average price of the three ($2,761,677), driven by large lakefront and golf-course estates in communities like Isleworth and Keene's Pointe. Its 118-day average time on market is also the longest, and its sale-to-list ratio (~94.5%, $1,494,756 sold vs. $1,581,065 listed) is the lowest of the three — signaling more negotiating room at this end of the market.
Winter Garden 475 active
Winter Garden has by far the deepest inventory and transaction volume of the three, with 475 active listings and 805 homes sold in the past 6 months. It's also the fastest-moving once under contract — just 35 days average — and posts the tightest sale-to-list ratio of the group at roughly 97.4%, a sign of strong, competitive buyer demand in this fast-growing family market.
Highest-Priced Active Listings
| City | Address Area | List Price | Beds | Baths | Living Sq Ft | DOM |
|---|---|---|---|---|---|---|
| Windermere | Windy Ridge Rd | $30,000,000 | 7 | 14 | 51,000 | 71 days |
| Winter Park | Preserve Point Dr | $8,950,000 | 7 | 11 | 11,255 | 310 days |
| Winter Garden | Lake Butler Blvd | $5,995,000 | 5 | 6 | 6,000 | 391 days |
Note: the Windermere listing above (51,000 sq ft) is an extreme outlier even for this luxury lake-estate market — worth a second look before repeating the figure publicly, though the underlying price-per-square-foot math is internally consistent.
What This Means for Buyers and Sellers
For Buyers
- Winter Garden offers the deepest active inventory of the three spotlighted cities, along with the fastest-closing pending pipeline — buyers there should be prepared to move decisively on well-priced listings
- Windermere's longer average days-on-market and lower sale-to-list ratio suggest real room to negotiate on price and terms at the top end of the market
- Working with a local agent like Bob McCranie helps buyers see which Orange County listings are priced in line with what's actually converting to contract
For Sellers
- Winter Park's high cost-per-square-foot ($495) reflects continued demand for its established, walkable neighborhoods
- Winter Garden sellers benefit from the tightest sale-to-list ratio in this comparison (~97.4%) — a strong market for pricing close to expectations
- A free home valuation from Bob McCranie, HomeSmart can show exactly where your property fits against these city-specific numbers
Explore More Orange County Cities
Bob McCranie maintains a live, filterable market report for cities across Orange County:
Frequently Asked: Orange County Market Data
- How many homes are for sale in Orange County right now? 3,525 active residential listings countywide.
- Which is more expensive: Winter Park, Windermere, or Winter Garden? Windermere currently has the highest average active-listing price at $2,761,677, followed by Winter Park at $1,430,753 and Winter Garden at $878,495.
- What's the average cost per square foot in Orange County? $309 countywide; $495 in Winter Park, $486 in Windermere, and $303 in Winter Garden.
- What's a typical sale-to-list price ratio in Orange County? About 97.1% countywide over the past 6 months — 97.4% in Winter Garden, 96.8% in Winter Park, and 94.5% in Windermere.
Get a Personalized Market Update for Your City
Bob McCranie has guided buyers and sellers through 24 years and 1,150+ closed transactions — backed by 45 five-star Google reviews. Whether you're buying in Winter Garden, selling in Winter Park, or exploring Windermere's lakefront estates, reach out for a breakdown of exactly how these numbers apply to your situation.
Bob McCranie · HomeSmart · Orlando Office
📞 972-754-0582 | ✉️ bobmccranie@gmail.com
Market data sourced from Bob McCranie's live Orange County market report. Figures reflect a point-in-time snapshot of active, under-contract, and recently sold listings and are deemed reliable but not guaranteed.