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.

218 homes with four or more bedrooms are for sale or pending in Windermere, FL today across 121 communities. The median asking price is $1,385,000, from $375,000 to $27,000,000. Listings in Windermere without that feature have a median of $449,950. Most listings right now: Isleworth (16), Keenes Pointe (16), Gotha Town (6). Updated September 11, 2026 from the MLS.

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	16	2	$4,600,000	$2,800,000
Keenes Pointe	16	1	$2,019,500	$940,000
Gotha Town	6	1	$1,422,500	$699,000
Westside Village	6	0	$1,044,500	$499,990
Windermere Town	5	1	$1,895,000	$1,099,000
Casabella	4	0	$3,495,000	$2,899,000
	4	1	$2,149,500	$1,995,000
Reserve At Lake Butler Sound	4	0	$1,522,000	$1,450,000
Bellaria	3	0	$2,800,000	$2,795,000
	3	0	$2,225,000	$1,900,000
Butler Bay	3	0	$1,649,000	$751,400
Windermere Isle	3	0	$1,085,000	$879,000
Windermere Trls Ph 3B	3	0	$1,075,000	$560,000
Windermere Isle Ph 2	3	0	$1,030,000	$775,000
Palms At Windermere	3	3	$989,990	$979,990
Chaine Du Lac	2	0	$10,000,000	$4,500,000
Casa Del Lago Rep	2	0	$4,245,000	$3,100,000
Weatherstone On Lake Olivia	2	0	$2,522,500	$2,395,000
Estates At Lake Clarice	2	0	$2,270,000	$2,090,000
Estancia/Windermere	2	0	$2,077,500	$1,985,000
Lake Butler Estates	2	0	$2,075,000	$850,000
Balmoral	2	0	$1,624,000	$1,399,000
Windsor Hill	2	0	$1,412,500	$1,375,000
Enclave	2	0	$1,409,000	$1,318,000
Lake Burden South Ph 2	2	0	$1,159,000	$448,000
Windermere Trls Ph 5B	2	0	$855,000	$795,000
Summerport Ph 05	2	0	$788,950	$779,900
Windermere Trls Ph 1C	2	0	$759,450	$519,900
Summerport	2	0	$747,450	$699,900
Belmere Village G2 48 65	2	0	$735,000	$725,000
	2	0	$729,000	$699,000
Windermere Sound	2	0	$710,495	$675,000
Windermere Terrace	2	0	$709,500	$639,000
	2	0	$695,499	$679,999
	2	0	$682,500	$645,000
	2	0	$644,450	$629,900
Lakes/Windermere Ph 02A	2	0	$624,700	$609,900
	2	0	$620,000	$560,000
Lakes/Windermere-Peachtree	2	0	$597,500	$500,000
Southbridge Village	2	0	$377,000	$375,000
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
	1	0	$7,695,000	$7,695,000
Down Acres Estates	1	0	$6,900,000	$6,900,000
Isleworth West	1	0	$6,900,000	$6,900,000
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	$3,999,999	$3,999,999
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
	1	0	$2,500,000	$2,500,000
Wauseon Ridge	1	0	$2,395,000	$2,395,000
Lake Down Shores	1	0	$2,275,000	$2,275,000

Also with 4-bedroom homes for sale

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?

As of September 11, 2026, 218 Windermere, FL listings whose MLS record reports four or more bedrooms are active or pending, across 121 communities. The count updates with every MLS refresh.

What do 4-bedroom homes cost in Windermere?

The median asking price today is $1,385,000, with listings from $375,000 to $27,000,000. Windermere listings without that feature have a median of $449,950.

Which Windermere community has the most 4-bedroom homes for sale?

Isleworth has the most right now (16), followed by Keenes Pointe (16), Gotha Town (6), Westside Village (6).

How much more does a 4-bedroom home cost?

It depends on the city and the age of the housing stock. The answer block on this page states today’s median asking price for four-plus-bedroom homes next to the median for other listings in the same city, and each listing page shows square footage so you can compare on a per-square-foot basis.

Keep exploring Windermere

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.

Listings courtesy of Stellar MLS as distributed by MLS GRID.