Golf Course Communities in Windermere, FL
Looking for golf course communities in Windermere, FL? Momentum tracks 18 Windermere communities with evidence of golf community living, each with MLS-derived pricing and market pace below — plus the local questions worth asking before you buy, and a direct line to an agent who works these communities.
Windermere golf course communities at a glance
The communities, by recent sales activity
| Community | City | Median price | 1-yr change | Days on mkt |
|---|---|---|---|---|
| Keene’s Pointe · agent | Windermere | $1.93M | – | 103 d |
| SUMMERPORT · agent | Windermere | $642,000 | – | 98 d |
| Town of Windermere · agent | Windermere | $905,000 | – | 72 d |
| BUTLER BAY · agent | Windermere | $1.50M | – | 37 d |
| KEENES POINTE 46/104 · agent | Windermere | $5.51M | – | 3 d |
| RESERVE AT LAKE BUTLER SOUND · agent | Windermere | $2.05M | – | 52 d |
| DAVIS SHORES · agent | Windermere | $1.16M | – | 85 d |
| TILDENS GROVE · agent | Windermere | $1.40M | – | 295 d |
| LAKE BUTLER ESTATES · agent | Windermere | $1.36M | – | 188 d |
| KEENE'S POINTE · agent | Windermere | $1.44M | – | 29 d |
| LAKES · agent | Windermere | $2.30M | – | – |
| ISLEWORTH WEST · agent | Windermere | $3.82M | – | – |
| ESTATES AT WINDERMERE · agent | Windermere | $1.32M | – | 71 d |
| MARINA BAY ESTATES · agent | Windermere | $1.68M | – | 1 d |
| LAKE DOWN WOODS · agent | Windermere | $1.39M | – | – |
| ISLEWORTH 5TH AMD | Windermere | – | – | – |
| Isleworth | Windermere | – | – | – |
| GARDENS/ISLEWORTH | Windermere | – | – | 47 d |
Communities are listed by recent closing volume in Momentum’s MLS data. Figures are aggregates, change over time, and are deemed reliable but not guaranteed.
Membership, fees and what “golf community” actually means
Golf communities range from public-course neighborhoods with no obligations to bundled-golf communities where equity membership is mandatory and priced into every sale. Before you offer, get the fee stack in writing: HOA dues, club or membership minimums, food-and-beverage minimums, cart fees, and any CDD assessment on the tax bill. Ask whether membership is mandatory, optional, or waitlisted, and what the initiation fee runs. A bundled-golf bargain can stop being a bargain once the full stack is on paper.
Resale considerations in golf communities
Course health matters to resale: a closed or struggling course next to your lot changes the value story. Ask how the course is funded, whether the club is member-owned or developer-owned, and whether any redevelopment litigation exists. Homes on the course trade at premiums that vary hole by hole — comps from the same street matter more here than anywhere.
What it costs to own here
At Orange County’s typical combined millage of 16.67 mills, a purchase at $1,438,000 (the median across these Windermere golf course communities) generates roughly $23,977 a year in property tax before exemptions — about $1,998 a month. Florida resets the assessed value to roughly your purchase price, so the seller’s current bill is not a preview of yours; a homesteaded owner then gets the $25,000–$50,000 exemption and the 3% Save Our Homes cap going forward. Citizens Property Insurance policies in Orange County average about $1,409 a year ($117 a month) — private-market quotes vary with roof age and wind mitigation, so price coverage before your inspection window closes. All-in, our county model puts the typical monthly cost of ownership in Orange County near $2,402 (principal and interest on the typical home, tax, and insurance).
Run your exact numbers: the property tax after purchase calculator uses Orange County’s verified millage, and the buyer closing costs calculator builds the full cash-to-close.
Demand and supply in Orange County right now
In the most recent IRS migration data (2022-2023), Orange County lost a net 9,037 people to relocation, with the largest inbound flows from NY, CA, NJ. Households moving IN reported average incomes of $66,457 versus $61,323 for those leaving — the income mix of demand, straight from tax filings. Population is up about 9.0% over the recent multi-year window. On the supply side, builders pulled 13,140 residential permits in Orange County in 2025 (4,221 single-family), up 63.2% year over year. Permits are tomorrow’s inventory: a shrinking pipeline supports prices, a swelling one hands buyers leverage. Our valuation model reads the county as overvalued by about 6.9% versus its income-and-rent fundamentals.
Explore more of Windermere
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Run the numbers in Orange County
- Find the best agent in Orange County
- Get a cash offer in Orange County
- Orange County housing scorecard
- What would selling net you
- Buyer closing costs calculator
Common questions
How many golf course communities does Windermere, FL have?
What do homes in Windermere golf course communities cost?
How does Momentum classify a community as one of the golf course communities?
How much is home insurance in Orange County?
What are property taxes like in Orange County?
Community classifications are compiled from MLS-reported amenities, verified amenity records and MLS build-year data, as of 2026-06-16; they are informational, change over time, and are deemed reliable but not guaranteed — verify details with each association. Not an offer of housing to any protected class to the exclusion of others. Equal Housing Opportunity.