- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
10 Properties Available In Windermere Town
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$2,599,000
Single Family Home
409 W 2ND AVE, Windermere, FL 34786
Welcome to Second Avenue, a serene peninsula in the heart of Old Windermere. This modern masterpiece offers 5 bedrooms, ...
Listed by UPSIDE REAL ESTATE INC


$2,800,000
Single Family Home
1003 OAKDALE ST, Windermere, FL 34786
Never Lived In Since Completely Remodeled and Expanded - Total of 6 Bedrooms - 5 Full Baths - 1 Pool or Guest Bath - Pri...
Listed by VINTAGE REALTY GROUP LLC


$8,895
Single Family Home
930 EAST BLVD, Windermere, FL 34786
Stunning newer LAKEFRONT construction in the heart of Downtown Windermere completed in July 2024. This exquisite single-...
Listed by THE SIMON SIMAAN GROUP


$4,899,000
Single Family Home
225 MAGNOLIA ST, Windermere, FL 34786
LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN <br>Unveiling a rare opportunity to own an architectural m...
Listed by COMPASS FLORIDA LLC


$6,450
Single Family Home
307 W 4TH AVE, Windermere, FL 34786
Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and a...
Listed by MAINFRAME REAL ESTATE


$1,300,000
Single Family Home
109 E 12TH AVE, Windermere, FL 34786
Welcome to this fully renovated four-bedroom, three-and-a-half-bath home in the heart of Windermere, just steps from Lak...
Listed by EXECUTIVE PROPERTIES


$2,295,000
Single Family Home
729 MAIN STREET, Windermere, FL 34786
This custom home is truly a gem, blending luxury, craftsmanship, and the charm of small-town Windermere living. The atte...
Listed by COLDWELL BANKER RESIDENTIAL RE


$1,995,000
Single Family Home
98 E 10TH AVE, Windermere, FL 34786
Stunning, thoughtfully designed, contemporary pool home, NEW (completed in 2024). Bright, open floor plan boasting 4 spa...
Listed by WATSON REALTY CORP.


$1,950,000
Single Family Home
830 OAKDALE ST, Windermere, FL 34786
RARE FIND IN DOWNTOWN WINDERMERE!! This immaculate home defines where luxury meets contemporary, nestled in the heart of...
Listed by CORCORAN PREMIER REALTY


$2,881,000
Single Family Home
325 MAGNOLIA ST, Windermere, FL 34786
PRICED BELOW APPRAISAL VALUE. Boasting a prime location in the Town of Windermere on Lake Down with access to the Butler...
Listed by REVEL REALTY LLC
