Gated Communities in Windermere, FL
Looking for gated communities in Windermere, FL? Momentum tracks 40 Windermere communities with evidence of gated 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 gated 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 |
| LAKESIDE/LKS/WINDERMERE · agent | Windermere | $305,000 | – | 19 d |
| GLENMUIR 48 39 · agent | Windermere | $865,000 | – | 62 d |
| WATERSTONE · agent | Windermere | $1.52M | – | 49 d |
| BELMERE VILLAGE G2 48 65 · agent | Windermere | $570,000 | – | 219 d |
| CASABELLA · agent | Windermere | $3.08M | – | 33 d |
| BUTLER BAY · agent | Windermere | $1.50M | – | 37 d |
| KEENES POINTE 46/104 · agent | Windermere | $5.51M | – | 3 d |
| LAKES/WINDERMERE-PEACHTREE · agent | Windermere | $560,000 | – | 207 d |
| GLENMUIR · agent | Windermere | $849,000 | – | 251 d |
| RESERVE AT LAKE BUTLER SOUND · agent | Windermere | $2.05M | – | 52 d |
| TILDENS GROVE · agent | Windermere | $1.40M | – | 295 d |
| OASIS COVE II/LAKESIDE VILLAGE PH · agent | Windermere | $335,000 | – | 30 d |
| RESERVE AT BELMERE · agent | Windermere | $818,000 | – | 52 d |
| CHAINE DU LAC · agent | Windermere | $3.15M | – | 54 d |
| GOTHA TOWN · agent | Windermere | $1.30M | – | 63 d |
| CASA DEL LAGO · agent | Windermere | $3.45M | – | 45 d |
| SAWYER SOUND · agent | Windermere | $2.73M | – | – |
| KEENE'S POINTE · agent | Windermere | $1.44M | – | 29 d |
| OXFORD MOOR 47/30 · agent | Windermere | $1.66M | – | – |
| ISLEWORTH WEST · agent | Windermere | $3.82M | – | – |
| ESTATES AT WINDERMERE · agent | Windermere | $1.32M | – | 71 d |
| LAKE DOWN CREST · agent | Windermere | $1.88M | – | – |
| EDEN ISLE · agent | Windermere | $650,000 | – | 45 d |
| SUMMERPORT BEACH · agent | Windermere | $1.70M | – | – |
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.
Every other tracked gated communities in Windermere
- HARBOR ISLE
- WEATHERSTONE ON LAKE OLIVIA
- OASIS COVE AT LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE #XI
- METCALF PARK REP
- BELLARIA
- LAKE DOWN RESERVE
- SUNSET BAY
- ISLEWORTH 5TH AMD
- LAKES OF WINDERMERE PEACHTREE
- BUTLER BAY,WINDERMERE CLUB
- BALMORAL
- EDEN ISLE BOAT RAMP
- Isleworth
- GARDENS/ISLEWORTH
What gates change about ownership
Controlled access typically comes with a manned gate, a transponder system, or both — funded through HOA dues. Expect guest-access procedures, delivery and contractor rules, and in some communities rental restrictions. Review the HOA budget for how the gate and any roving patrol are funded, and whether roads are private (the HOA maintains them — another line in the dues) or public.
Due diligence before you buy behind a gate
Request the HOA documents early: budget, reserves, rules, and the last two years of meeting minutes. Private roads, gates and common areas are owner-funded, so thin reserves become special assessments. Our buyer closing costs calculator helps you model dues and assessments into the real monthly cost.
What it costs to own here
At Orange County’s typical combined millage of 16.67 mills, a purchase at $1,469,000 (the median across these Windermere gated communities) generates roughly $24,494 a year in property tax before exemptions — about $2,041 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.
Live inventory, refreshed nightly from the MLS.
Live gated-community listings in Windermere
47 active listings carry the flag today (27% of Windermere inventory), median asking $1,849,000, $473/sq ft, median 72 days on market. Photo cards link to the listing; refreshed nightly.
Newest gated community homes in Windermere
The most expensive gated community homes in Windermere
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 6119 Grosvenor Shore Drive | $15,900,000 | 14,068 | Keenes Point |
| 12488 Park Avenue | $15,500,000 | 13,425 | Chaine Du Lac |
| 3057 Porto Lago Court | $13,995,000 | 12,067 | Lake Down Pointe |
| 9317 Gladys Garden Court | $7,999,000 | 8,038 | Gardens/Isleworth |
| 9349 Tibet Pointe Circle | $6,995,000 | 7,529 | Keenes Pointe |
| 6055 Louise Cove Drive | $6,900,000 | 7,158 | Isleworth West |
| 8342 Boyla Court | $6,700,000 | 8,133 | Keenes Pointe |
| 12264 Montalcino Circle | $5,390,000 | 7,872 | Casa Del Lago |
| 9721 Carillon Park Drive | $4,778,000 | 8,305 | Keenes Pointe |
| 6719 Valhalla Way | $4,495,000 | 6,159 | Keenes Pointe |
Gated Community Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 1 | 2% |
| $300Kâ$500K | 2 | 4% |
| $500Kâ$750K | 6 | 13% |
| $750Kâ$1M | 1 | 2% |
| $1M+ | 37 | 79% |
Windermere gated community homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Gated Community Homes | New build | Median list | From |
|---|---|---|---|---|
| Keenes Pointe | 14 | 1 | $2,245,000 | $940,000 |
| Casabella | 3 | 0 | $3,700,000 | $2,899,000 |
| Reserve At Belmere Ph 02 48 144 | 3 | 0 | $2,225,000 | $1,900,000 |
| Reserve At Lake Butler Sound | 3 | 0 | $1,549,000 | $1,495,000 |
| Chaine Du Lac | 2 | 0 | $10,000,000 | $4,500,000 |
| Casa Del Lago Rep | 2 | 0 | $4,245,000 | $3,100,000 |
| Bellaria | 2 | 0 | $2,997,500 | $2,795,000 |
| Weatherstone On Lake Olivia | 2 | 0 | $2,522,500 | $2,395,000 |
| Butler Bay | 2 | 0 | $1,699,500 | $1,649,000 |
| Balmoral | 2 | 0 | $1,624,000 | $1,399,000 |
| Belmere Village G2 48 65 | 2 | 0 | $735,000 | $725,000 |
| Lakes/Windermere-Peachtree | 2 | 0 | $594,500 | $500,000 |
| Lakeside At Lakes Of Windermere | 2 | 0 | $325,000 | $320,000 |
| Lakeside/Lks/Windermere | 2 | 0 | $310,000 | $295,000 |
| Keenes Point | 1 | 0 | $15,900,000 | $15,900,000 |
| Lake Down Pointe 50 42 | 1 | 0 | $13,995,000 | $13,995,000 |
| Isleworth 5Th Amd | 1 | 0 | $12,350,000 | $12,350,000 |
| Gardens/Isleworth | 1 | 1 | $7,999,000 | $7,999,000 |
| Keenes Pointe Unit 03 46/104 | 1 | 0 | $7,695,000 | $7,695,000 |
| Isleworth West | 1 | 0 | $6,900,000 | $6,900,000 |
| Sunset Bay | 1 | 0 | $4,995,000 | $4,995,000 |
| Gotha Town | 1 | 0 | $4,750,000 | $4,750,000 |
| Keenes Pointe 46/104 | 1 | 0 | $4,495,000 | $4,495,000 |
| Metcalf Park Rep | 1 | 0 | $3,999,999 | $3,999,999 |
| Lake Davis Reserve A & B | 1 | 0 | $2,500,000 | $2,500,000 |
| Waterford Pointe Ph 02 Rep | 1 | 0 | $2,150,000 | $2,150,000 |
| Keene'S Pointe | 1 | 0 | $1,795,000 | $1,795,000 |
| Casa Del Lago-Replat | 1 | 0 | $1,595,000 | $1,595,000 |
| Waterstone | 1 | 0 | $1,575,000 | $1,575,000 |
| Casa Del Lago | 1 | 0 | $1,395,000 | $1,395,000 |
| Butler Bay,Windermere Club | 1 | 0 | $1,350,000 | $1,350,000 |
| Oxford Moor 47/30 | 1 | 0 | $1,289,000 | $1,289,000 |
| Reserve At Belmere | 1 | 0 | $1,275,000 | $1,275,000 |
| Estates At Windermere | 1 | 0 | $1,169,900 | $1,169,900 |
| Westover Club Ph 01 44/139 | 1 | 0 | $969,000 | $969,000 |
| Glenmuir | 1 | 0 | $809,000 | $809,000 |
| Eden Isle Boat Ramp | 1 | 0 | $699,900 | $699,900 |
| Eden Isle | 1 | 0 | $690,000 | $690,000 |
| Belmere Village G-5 | 1 | 0 | $629,900 | $629,900 |
| Belmere Village | 1 | 0 | $625,000 | $625,000 |
| Oasis Cove Ii/Lakeside Village Ph | 1 | 0 | $399,999 | $399,999 |
| Oasis Cove/Lakeside Village Ph Vii | 1 | 0 | $359,900 | $359,900 |
| Oasis Cove I/Lakeside Village Ph 01 | 1 | 0 | $330,000 | $330,000 |
Explore more of Windermere
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Run the numbers in Orange County
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- Orange County housing scorecard
- What would selling net you
- Buyer closing costs calculator
Common questions
How many gated communities does Windermere, FL have?
What do homes in Windermere gated communities cost?
How does Momentum classify a community as one of the gated 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.