Pool Homes for Sale in Windermere, FL
Buyers who want a pool search for the pool first. This page tracks every Windermere listing whose MLS record reports a private pool, by community, with live counts and asking prices, and what the pool adds to the cost of ownership.
150 homes with a private pool are for sale or pending in Windermere, FL today across 81 communities. The median asking price is $2,185,000, from $540,000 to $27,000,000. Listings in Windermere without that feature have a median of $579,857. Most listings right now: Isleworth (25), Keenes Pointe (12), Reserve At Lake Butler Sound (5). Updated September 27, 2026 from the MLS.
Live pool homes in Windermere: the listings
104 active listings carry the flag today (53% of Windermere inventory), median asking $2,742,500, $531/sq ft, median 55 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Windermere
The most expensive pool homes in Windermere
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 5036 Latrobe Drive | $18,750,000 | 15,337 | Isleworth |
| 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 |
| 9323 Gladys Garden Court | $11,900,000 | 9,770 | Isleworth |
| 9832 Laurel Valley Drive | $11,750,000 | 11,100 | Isleworth |
| 9317 Gladys Garden Court | $7,999,000 | 8,038 | Gardens/Isleworth |
| 5074 Isleworth Country Club Drive | $7,250,000 | 7,099 | Isleworth |
| 5373 Isleworth Country Club Drive | $7,200,000 | 5,993 | Isleworth |
| 9349 Tibet Pointe Circle | $6,995,000 | 7,529 | Keenes Pointe |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| $500Kâ$750K | 4 | 4% |
| $750Kâ$1M | 8 | 8% |
| $1M+ | 92 | 88% |
Windermere pool homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most pool homes listed are tabled; the rest follow.
| Community | Pool Homes | New build | Median list | From |
|---|---|---|---|---|
| Isleworth | 25 | 3 | $4,100,000 | $2,800,000 |
| Keenes Pointe | 12 | 1 | $2,362,000 | $940,000 |
| Reserve At Lake Butler Sound | 5 | 0 | $1,495,000 | $1,100,000 |
| Casabella | 4 | 0 | $3,435,000 | $2,899,000 |
| Gotha Town | 4 | 1 | $2,752,500 | $1,090,000 |
| Windermere | 3 | 1 | $2,200,000 | $1,945,000 |
| Westside Village | 3 | 0 | $1,290,000 | $1,159,000 |
| Chaine Du Lac | 2 | 0 | $10,000,000 | $4,500,000 |
| Casa Del Lago Rep | 2 | 0 | $4,245,000 | $3,100,000 |
| Windermere Town | 2 | 0 | $2,597,500 | $1,895,000 |
| Weatherstone On Lake Olivia | 2 | 0 | $2,395,000 | $2,290,000 |
| Lake Butler Estates | 2 | 0 | $2,387,500 | $1,775,000 |
| Estates At Lake Clarice | 2 | 0 | $2,270,000 | $2,090,000 |
| Estancia/Windermere | 2 | 0 | $2,077,500 | $1,985,000 |
| Butler Bay | 2 | 0 | $1,699,500 | $1,649,000 |
| Enclave | 2 | 0 | $1,409,000 | $1,318,000 |
| Windsor Hill | 2 | 0 | $1,385,000 | $1,375,000 |
| Windermere Downs | 2 | 0 | $1,222,500 | $1,150,000 |
| Windermere Isle | 2 | 0 | $1,123,000 | $850,000 |
| Windermere Isle Ph 2 | 2 | 0 | $902,500 | $775,000 |
| Summerport | 2 | 0 | $739,950 | $699,900 |
| West Point Commons | 2 | 0 | $710,000 | $540,000 |
| Isleworth Amd 03 | 1 | 0 | $19,500,000 | $19,500,000 |
| Keenes Point | 1 | 0 | $15,900,000 | $15,900,000 |
| Lake Down Pointe 50 42 | 1 | 0 | $13,995,000 | $13,995,000 |
| Gardens/Isleworth | 1 | 1 | $7,999,000 | $7,999,000 |
| Keenes Pointe Unit 03 46/104 | 1 | 0 | $7,450,000 | $7,450,000 |
| Isleworth West | 1 | 0 | $6,900,000 | $6,900,000 |
| Down Acres Estates | 1 | 0 | $6,800,000 | $6,800,000 |
| Aladar On Lake Butler | 1 | 0 | $5,999,000 | $5,999,000 |
| Lake Olivia Reserve | 1 | 1 | $5,500,000 | $5,500,000 |
| Sunset Bay | 1 | 0 | $4,995,000 | $4,995,000 |
| Keenes Pointe 46/104 | 1 | 0 | $4,495,000 | $4,495,000 |
| Saddlecrest At Windermere | 1 | 1 | $4,276,160 | $4,276,160 |
| Gardens/Isleworth Un #2 | 1 | 0 | $3,990,000 | $3,990,000 |
| Metcalf Park Rep | 1 | 0 | $3,950,000 | $3,950,000 |
| Casabella Ph 2 | 1 | 0 | $3,599,000 | $3,599,000 |
| Lake Roper Pointe | 1 | 0 | $3,200,000 | $3,200,000 |
| Lake Hancock Shores | 1 | 0 | $3,100,000 | $3,100,000 |
| Down Point Sub | 1 | 0 | $2,950,000 | $2,950,000 |
| Bellaria | 1 | 0 | $2,800,000 | $2,800,000 |
| Lake Davis Reserve A & B | 1 | 0 | $2,500,000 | $2,500,000 |
| Lake Down Shores | 1 | 0 | $2,275,000 | $2,275,000 |
| Waterford Pointe Ph 02 Rep | 1 | 0 | $2,150,000 | $2,150,000 |
| Reserve At Belmere Ph 02 48 144 | 1 | 0 | $1,900,000 | $1,900,000 |
| Lake Crescent Reserve | 1 | 0 | $1,830,000 | $1,830,000 |
| Keene'S Pointe | 1 | 0 | $1,795,000 | $1,795,000 |
| Waterford Pointe Ph 1 Reserve | 1 | 0 | $1,599,000 | $1,599,000 |
| Casa Del Lago-Replat | 1 | 0 | $1,595,000 | $1,595,000 |
| Farms | 1 | 0 | $1,575,000 | $1,575,000 |
| Waterstone | 1 | 0 | $1,575,000 | $1,575,000 |
| Marina Bay Estates | 1 | 0 | $1,500,000 | $1,500,000 |
| Lake Cawood Ests Rep | 1 | 0 | $1,500,000 | $1,500,000 |
| Tildens Grove Ph 01 47/65 | 1 | 0 | $1,488,000 | $1,488,000 |
| Lake Down Cove | 1 | 0 | $1,399,900 | $1,399,900 |
| Balmoral | 1 | 0 | $1,399,000 | $1,399,000 |
| Town Of Windermere | 1 | 0 | $1,395,000 | $1,395,000 |
| Casa Del Lago | 1 | 0 | $1,395,000 | $1,395,000 |
| Isles Windermere | 1 | 0 | $1,375,000 | $1,375,000 |
| Butler Bay,Windermere Club | 1 | 0 | $1,350,000 | $1,350,000 |
Also with pool homes for sale
- Oxford Moor 47/30 (1)
- Reserve At Belmere (1)
- Willows At Lake Rhea Ph 03 (1)
- Estates At Windermere (1)
- Windermere Trls Ph 3B (1)
- Willows At Lake Rhea (1)
- Windermere Trls Ph 5A (1)
- Manors At Butler Bay Ph 02 (1)
- Westover Club Ph 01 44/139 (1)
- Willows At Lake Rhea Ph 01 (1)
- Windermere Trails (1)
- Windermere Trls Ph 5B (1)
- Windermere Trls (1)
- Lake Sawyer South Ph 05 (1)
- Providence Ph 01 50 03 (1)
- Eden Isle (1)
- Summerport Phase 1 (1)
- Windermere Sound (1)
- Silver Woods Ph 02 (1)
- Silver Woods Ph 05 (1)
- Wickham Park (1)
What a private pool actually costs to own
Budget three things beyond the price: the pool itself (chemicals, pump electricity and a service if you do not want to do it yourself typically run $150 to $300 a month), the screen enclosure where there is one (a full re-screen every 8 to 12 years; a replacement enclosure is a five-figure job after a storm), and insurance, where a pool adds liability exposure and many carriers require a fence, self-latching gate or approved alarm. Florida’s Residential Swimming Pool Safety Act requires at least one safety feature on a new pool, and lenders and insurers ask about it on older ones. Have the pool inspected separately from the house: the pump, heater, surface finish and deck are the expensive items. Our true cost of ownership calculator puts insurance, taxes and upkeep into one monthly number.
Questions to ask about any pool listing
How old are the pump, filter and heater, and is there a warranty? When was the surface last refinished? Is the enclosure permitted and when was it last re-screened? Is there a barrier or alarm that satisfies the insurer? What did the seller pay for homeowners insurance last year, and did the carrier require anything for the pool? A local agent who works the area will know which enclosures came through the last storm.
Common questions
How many homes with a private pool are for sale in Windermere?
What do pool homes cost in Windermere?
Which Windermere community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Windermere
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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 private pool. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.