Waterfront Homes for Sale in Windermere, FL
This page tracks every Windermere listing whose MLS record reports waterfront (ocean, bay, Intracoastal, river, canal or lake frontage), by community, with live counts and asking prices, and the costs that come with the water.
54 waterfront homes are for sale or pending in Windermere, FL today across 37 communities. The median asking price is $3,100,000, from $600,000 to $27,000,000. Listings in Windermere without that feature have a median of $760,000. Most listings right now: Keenes Pointe (5), Isleworth (4), Windermere Town (3). Updated September 27, 2026 from the MLS.
Live waterfront homes in Windermere: the listings
31 active listings carry the flag today (16% of Windermere inventory), median asking $3,950,000, $724/sq ft, median 73 days on market. Photo cards link to the listing; refreshed nightly.
Newest waterfront homes in Windermere
The most expensive waterfront 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 |
| 9832 Laurel Valley Drive | $11,750,000 | 11,100 | Isleworth |
| 9349 Tibet Pointe Circle | $6,995,000 | 7,529 | Keenes Pointe |
| 6055 Louise Cove Drive | $6,900,000 | 7,158 | Isleworth West |
| 9061 Ron Den Lane | $6,800,000 | 6,300 | Down Acres Estates |
| 8342 Boyla Court | $6,700,000 | 8,133 | Keenes Pointe |
| 6462 Deacon Cir | $6,595,000 | 7,178 | Isleworth |
Waterfront Homes by price
| Band | For sale | Share |
|---|---|---|
| $750Kâ$1M | 1 | 3% |
| $1M+ | 30 | 97% |
Windermere waterfront homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Waterfront Homes | New build | Median list | From |
|---|---|---|---|---|
| Keenes Pointe | 5 | 1 | $4,778,000 | $1,151,000 |
| Isleworth | 4 | 1 | $9,172,500 | $5,975,000 |
| Windermere Town | 3 | 0 | $1,895,000 | $1,600,000 |
| Chaine Du Lac | 2 | 0 | $10,000,000 | $4,500,000 |
| Weatherstone On Lake Olivia | 2 | 0 | $2,395,000 | $2,290,000 |
| Butler Bay | 2 | 0 | $1,699,500 | $1,649,000 |
| Summerport | 2 | 0 | $739,950 | $699,900 |
| 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 |
| Isleworth 5Th Amd | 1 | 0 | $12,350,000 | $12,350,000 |
| Windermere | 1 | 0 | $7,500,000 | $7,500,000 |
| 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 |
| Sunset Bay | 1 | 0 | $4,995,000 | $4,995,000 |
| Gotha Town | 1 | 0 | $4,750,000 | $4,750,000 |
| Metcalf Park Rep | 1 | 0 | $3,950,000 | $3,950,000 |
| Lake Roper Pointe | 1 | 0 | $3,200,000 | $3,200,000 |
| Lake Hancock Shores | 1 | 0 | $3,100,000 | $3,100,000 |
| Casa Del Lago Rep | 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 Down Shores | 1 | 0 | $2,275,000 | $2,275,000 |
| Estates At Lake Clarice | 1 | 0 | $2,090,000 | $2,090,000 |
| Estancia/Windermere | 1 | 0 | $1,985,000 | $1,985,000 |
| Reserve At Belmere Ph 02 48 144 | 1 | 0 | $1,900,000 | $1,900,000 |
| Lake Burden South Ph 2 | 1 | 0 | $1,870,000 | $1,870,000 |
| Keene'S Pointe | 1 | 0 | $1,795,000 | $1,795,000 |
| Davis Shores | 1 | 0 | $1,572,000 | $1,572,000 |
| Oxford Moor 47/30 | 1 | 0 | $1,289,000 | $1,289,000 |
| Sandy Shores | 1 | 0 | $1,225,000 | $1,225,000 |
| Providence Ph 01 50 03 | 1 | 0 | $720,000 | $720,000 |
| Eden Isle Boat Ramp | 1 | 0 | $699,900 | $699,900 |
| Lakes/Windermere Ph 02A | 1 | 0 | $625,000 | $625,000 |
| Summerport Phase 1 | 1 | 0 | $600,000 | $600,000 |
What waterfront ownership really costs
Waterfront homes carry costs inland homes do not: flood insurance where the parcel sits in a FEMA special flood hazard area, higher windstorm premiums closer to open water, and upkeep for seawalls, docks and lifts. Before you offer, pull the FEMA flood zone for the specific parcel, ask for the seawall’s age and any inspection reports, and get an insurance quote in hand, not an estimate. Our flood insurance calculator and wind mitigation savings calculator show what the parcel will actually cost to insure.
Questions to ask about any waterfront listing
Is the water frontage deeded or association-owned? Is there a fixed bridge between the dock and open water, and what is the clearance? What did the seller pay for flood and wind coverage last year, and with which carriers? Has the seawall or dock been permitted and inspected? What is the finished-floor elevation? A local agent who works waterfront deals will know which canals hold depth at low tide and which carriers are writing in the area.
Common questions
How many waterfront homes are for sale in Windermere?
What do waterfront homes cost in Windermere?
Which Windermere community has the most waterfront homes for sale?
Is a waterfront home always in a flood zone?
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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 waterfront. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.