Gated Communities in Windermere, FL: Homes for Sale
This page tracks every Windermere listing whose MLS record reports a gated community (manned gate, unmanned gate or security gate), by community, with live counts and asking prices, and the fee questions that come with the gate.
96 homes in gated communities are for sale or pending in Windermere, FL today across 47 communities. The median asking price is $2,575,000, from $295,000 to $27,000,000. Listings in Windermere without that feature have a median of $1,424,950. Most listings right now: Isleworth (18), Keenes Pointe (14), Casabella (3). Updated September 9, 2026 from the MLS.
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 |
|---|---|---|---|---|
| Isleworth | 18 | 2 | $4,000,000 | $2,800,000 |
| Keenes Pointe | 14 | 1 | $2,245,000 | $940,000 |
| Casabella | 3 | 0 | $3,700,000 | $2,899,000 |
| 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 | $3,225,000 | $3,200,000 |
| 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 |
| Eden Isle | 2 | 0 | $667,500 | $640,000 |
| 2 | 0 | $364,950 | $330,000 | |
| 2 | 0 | $325,000 | $320,000 | |
| Lakeside/Lks/Windermere | 2 | 0 | $310,000 | $295,000 |
| 1 | 0 | $15,900,000 | $15,900,000 | |
| 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 |
| 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 | $4,850,000 | $4,850,000 |
| 1 | 0 | $4,500,000 | $4,500,000 | |
| Keenes Pointe 46/104 | 1 | 0 | $4,495,000 | $4,495,000 |
| Metcalf Park Rep | 1 | 0 | $3,999,999 | $3,999,999 |
| Lake Down Reserve | 1 | 1 | $3,950,000 | $3,950,000 |
| 1 | 0 | $2,500,000 | $2,500,000 | |
| 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 |
| 1 | 0 | $969,000 | $969,000 | |
| Glenmuir | 1 | 0 | $809,000 | $809,000 |
| Eden Isle Boat Ramp | 1 | 0 | $724,900 | $724,900 |
| Lakes/Windermere-Peachtree | 1 | 0 | $695,000 | $695,000 |
| 1 | 0 | $629,900 | $629,900 | |
| 1 | 0 | $625,000 | $625,000 | |
| 1 | 0 | $439,000 | $439,000 | |
| Oasis Cove Ii/Lakeside Village Ph | 1 | 0 | $399,999 | $399,999 |
| 1 | 0 | $359,900 | $359,900 |
What the gate costs and what it actually does
A gate is an HOA amenity, so it shows up in dues: an unmanned keypad or transponder gate adds little; a 24-hour manned gate is a six-figure annual staffing line shared by the homeowners, and the roads behind it are usually private, which means the association, not the county, pays to repave them. Ask for the current HOA budget and reserve study, whether the roads are private, and whether a gate or road assessment is pending. The MLS field records the gate, not its staffing, so confirm which kind it is before you value it. Our true cost of ownership calculator puts HOA dues, taxes and insurance into one monthly number.
Questions to ask about any gated-community listing
Is the gate manned, and during what hours? Are the roads private, and what do the reserves look like for repaving? What are the HOA dues today and what did they run three years ago? Is there a CDD or a special assessment on the books? What are the guest-access and delivery rules? A local agent who works the community will know which gates are staffed and which associations are underfunded.
Common questions
How many homes in gated communities are for sale in Windermere?
What do gated community homes cost in Windermere?
Which Windermere community has the most gated community homes for sale?
Are gated communities more expensive to own?
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Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Windermere, FL whose MLS record reports a gated community. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.