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.
50 waterfront homes are for sale or pending in Windermere, FL today across 36 communities. The median asking price is $2,974,998, from $625,000 to $27,000,000. Listings in Windermere without that feature have a median of $737,995. Most listings right now: Keenes Pointe (4), Windermere Town (3), Chaine Du Lac (2). Updated October 17, 2026 from the MLS.
Live waterfront homes in Windermere: the listings
38 active listings carry the flag today (18% of Windermere inventory), median asking $3,250,000, $687/sq ft, median 66 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 |
|---|---|---|---|
| 5603 Marleon Drive | $27,000,000 | 22,108 | — |
| 5192 Vardon Drive | $19,500,000 | 13,494 | — |
| 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 |
| 9312 Blanche Cove Dr | $12,350,000 | 11,465 | Isleworth |
| 4226 Downeast Lane | $9,750,000 | 5,316 | — |
| 9343 Tibet Pointe Circle | $7,450,000 | 8,362 | — |
| 6113 Grosvenor Shore Drive | $6,950,000 | 8,722 | Keenes Pointe |
| 6055 Louise Cove Drive | $6,900,000 | 7,158 | Isleworth West |
Waterfront Homes by price
| Band | For sale | Share |
|---|---|---|
| $500K–$750K | 1 | 3% |
| $750K–$1M | 2 | 5% |
| $1M+ | 35 | 92% |
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 | 4 | 1 | $5,739,000 | $2,250,000 |
| Windermere Town | 3 | 0 | $1,895,000 | $1,498,000 |
| Chaine Du Lac | 2 | 0 | $10,000,000 | $4,500,000 |
| Lake Down Shores | 2 | 0 | $3,312,500 | $2,275,000 |
| Weatherstone On Lake Olivia | 2 | 0 | $2,395,000 | $2,290,000 |
| 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 | $5,600,000 | $5,600,000 |
| Sunset Bay | 1 | 0 | $4,945,000 | $4,945,000 |
| 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 |
| Casa Del Lago Rep | 1 | 0 | $3,100,000 | $3,100,000 |
| Lake Hancock Shores | 1 | 0 | $2,999,996 | $2,999,996 |
| Down Point Sub | 1 | 0 | $2,950,000 | $2,950,000 |
| Bellaria | 1 | 0 | $2,795,000 | $2,795,000 |
| Sawyer Shores Sub | 1 | 1 | $2,190,000 | $2,190,000 |
| 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 |
| Balmoral | 1 | 0 | $1,795,000 | $1,795,000 |
| Butler Bay | 1 | 0 | $1,725,000 | $1,725,000 |
| 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 |
| Windermere Isle-Ph 2 | 1 | 0 | $950,000 | $950,000 |
| 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 |
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?
Keep exploring Windermere
- All homes for sale in Windermere
- Windermere pool homes
- Windermere golf course homes
- Windermere gated community homes
- Windermere 4-bedroom homes
- Windermere homes $300K–$500K
- Waterfront Homes in every city
Waterfront Homes in nearby Orange County cities
- Orlando waterfront homes (258 for sale)
- Winter Garden waterfront homes (44 for sale)
- Winter Park waterfront homes (24 for sale)
- Maitland waterfront homes (15 for sale)
- Apopka waterfront homes (13 for sale)
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.