4 Bedroom Homes for Sale in Windermere, FL
Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Windermere listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.
225 homes with four or more bedrooms are for sale or pending in Windermere, FL today across 126 communities. The median asking price is $1,375,000, from $375,000 to $27,000,000. Listings in Windermere without that feature have a median of $450,000. Most listings right now: Isleworth (22), Keenes Pointe (16), Westside Village (6). Updated October 2, 2026 from the MLS.
Live 4-bedroom homes in Windermere: the listings
174 active listings match today (75% of Windermere inventory), median asking $1,495,000, $406/sq ft, median 50 days on market. Photo cards link to the listing; refreshed nightly.
Newest 4-bedroom homes in Windermere
The most expensive 4-bedroom homes in Windermere
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 5603 Marleon Drive | $27,000,000 | 22,108 | — |
| 5192 Vardon Drive | $19,500,000 | 13,494 | — |
| 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 |
| 4226 Downeast Lane | $9,750,000 | 5,316 | — |
| 5092 Isleworth Country Club Drive | $8,500,000 | 7,100 | Isleworth |
4-Bedroom Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 5 | 3% |
| $500K–$750K | 27 | 16% |
| $750K–$1M | 25 | 14% |
| $1M+ | 117 | 67% |
Windermere 4-bedroom 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 4-bedroom homes listed are tabled; the rest follow.
| Community | 4-Bedroom Homes | New build | Median list | From |
|---|---|---|---|---|
| Isleworth | 22 | 3 | $5,149,750 | $2,800,000 |
| Keenes Pointe | 16 | 1 | $2,362,000 | $940,000 |
| Westside Village | 6 | 0 | $959,500 | $499,990 |
| Gotha Town | 5 | 1 | $1,695,000 | $990,000 |
| Windermere Town | 5 | 0 | $1,599,000 | $1,089,000 |
| Casabella | 4 | 0 | $3,435,000 | $2,899,000 |
| Windermere | 4 | 1 | $2,149,500 | $1,945,000 |
| Reserve At Lake Butler Sound | 4 | 0 | $1,472,500 | $1,100,000 |
| Palms At Windermere | 4 | 4 | $1,040,490 | $979,990 |
| Butler Bay | 3 | 0 | $1,649,000 | $751,400 |
| Windermere Isle | 3 | 0 | $1,085,000 | $850,000 |
| Windermere Trls Ph 3B | 3 | 0 | $1,075,000 | $560,000 |
| Lake Sawyer South Ph 01 | 3 | 0 | $679,999 | $649,000 |
| Lakes/Windermere Ph 02A | 3 | 0 | $625,000 | $609,900 |
| 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 | $2,897,500 | $2,800,000 |
| Weatherstone On Lake Olivia | 2 | 0 | $2,395,000 | $2,290,000 |
| Estancia/Windermere | 2 | 0 | $2,077,500 | $1,985,000 |
| Waterstone | 2 | 0 | $1,962,500 | $1,575,000 |
| 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 |
| Lake Burden South Ph 2 | 2 | 0 | $1,154,500 | $439,000 |
| Windermere Isle Ph 2 | 2 | 0 | $902,500 | $775,000 |
| Summerport Ph 05 | 2 | 0 | $788,950 | $779,900 |
| Windermere Trls Ph 1C | 2 | 0 | $759,449 | $519,900 |
| Summerport | 2 | 0 | $739,950 | $699,900 |
| Belmere Village G2 48 65 | 2 | 0 | $727,500 | $725,000 |
| Windermere Sound | 2 | 0 | $710,495 | $675,000 |
| West Point Commons | 2 | 0 | $705,000 | $530,000 |
| Ashlin Park Ph 2 | 2 | 0 | $700,000 | $645,000 |
| Providence Ph 01 50 03 | 2 | 0 | $682,500 | $645,000 |
| Lake Sawyer South | 2 | 0 | $644,450 | $629,900 |
| Lakes Windermere Ph 01 49 108 | 2 | 0 | $620,000 | $560,000 |
| Lakes/Windermere-Peachtree | 2 | 0 | $594,500 | $500,000 |
| 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 |
| 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 | $7,450,000 | $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 |
| 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 |
| Lake Butler Estates | 1 | 0 | $3,000,000 | $3,000,000 |
| Down Point Sub | 1 | 0 | $2,950,000 | $2,950,000 |
| Lake Davis Reserve A & B | 1 | 0 | $2,500,000 | $2,500,000 |
| Estates At Lake Clarice | 1 | 0 | $2,450,000 | $2,450,000 |
| Wauseon Ridge | 1 | 0 | $2,299,000 | $2,299,000 |
| Lake Down Shores | 1 | 0 | $2,275,000 | $2,275,000 |
| Windermere Town Rep | 1 | 1 | $2,175,000 | $2,175,000 |
Also with 4-bedroom homes for sale
- Waterford Pointe Ph 02 Rep (1)
- Reserve At Belmere Ph 02 48 144 (1)
- Lake Crescent Reserve (1)
- Keene'S Pointe (1)
- Casa Del Lago-Replat (1)
- Farms (1)
- Davis Shores (1)
- Marina Bay Estates (1)
- Lake Cawood Ests Rep (1)
- Tildens Grove Ph 01 47/65 (1)
- Town Of Windermere (1)
- Casa Del Lago (1)
- Balmoral (1)
- Isles Windermere (1)
- Butler Bay,Windermere Club (1)
- Lake Down Cove (1)
- Oxford Moor 47/30 (1)
- Reserve At Belmere (1)
- Palms/Windermere (1)
- Sandy Shores (1)
- Willows At Lake Rhea Ph 03 (1)
- Estates At Windermere (1)
- Windermere Lndgs Fd-1 (1)
- Whitney Isles/Belmere Ph 02 (1)
- Gotha Town (1)
- Willows At Lake Rhea (1)
- Windermere Trls Ph 5A (1)
- Glenmuir Ut 02 51 42 (1)
- Manors At Butler Bay Ph 02 (1)
- Lake Buynak Estates (1)
- Westover Club Ph 01 44/139 (1)
- Willows At Lake Rhea Ph 01 (1)
- Windermere Isle-Ph 2 (1)
- Windermere Trails (1)
- Windstone (1)
- Glenmuir 48 39 (1)
- Reserve/Belmere Ph 04 (1)
- Windermere Trls (1)
- Peachtree Park (1)
- Windermere Trls Ph 5B (1)
- Vineyards/Horizons West Ph 18 (1)
- Lake Sawyer South Ph 05 (1)
- Providence Ph 02 (1)
- Windermere Trls Ph 4B (1)
- Stillwater Xings Prcl Sc-13 Ph (1)
- Eden Isle Boat Ramp (1)
- Eden Isle (1)
- Vineyards Of Horizons West Phase 1B (1)
- Summerport Edens Hammock (1)
- Windermere Terrace (1)
- Lake Sawyer South Ph 1 (1)
- Belmere Village G-5 (1)
- Summerport Trl (1)
- Lake Sawyer South Ph 02 (1)
- Wickham Park (1)
- Summerport Phase 1 (1)
- Silver Woods Ph 05 (1)
- Preston Square (1)
- Royal Estates (1)
- Summerport Ph 5 (1)
- Lakes Of Windermere-Peachtree (1)
- Windermere Sound Ph 2 (1)
- Windermere Sound Ph 2 (1)
- Windermere Trls Prcl 3 (1)
- Tennyson Pk/Summerport (1)
- Southbridge Village (1)
What the fourth bedroom costs
The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.
Questions to ask about any four-bedroom listing
Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.
Common questions
How many homes with four or more bedrooms are for sale in Windermere?
What do 4-bedroom homes cost in Windermere?
Which Windermere community has the most 4-bedroom homes for sale?
How much more does a 4-bedroom home cost?
Keep exploring Windermere
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4-Bedroom Homes in nearby Orange County cities
- Orlando 4-bedroom homes (1645 for sale)
- Winter Garden 4-bedroom homes (499 for sale)
- Apopka 4-bedroom homes (341 for sale)
- Winter Park 4-bedroom homes (166 for sale)
- Ocoee 4-bedroom homes (100 for sale)
- Maitland 4-bedroom homes (39 for sale)
- Oakland 4-bedroom homes (33 for sale)
- Belle Isle 4-bedroom 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 four or more bedrooms. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.