New72$1,189,000
5 bd · 5 ba · 4,999 sqft
17538 Black Rail St, Windermere, FL
Mauro Mateo · KARDOSH REALTY
Luxury Homes in Windermere, FL
Hide MapLuxury Homes in Windermere, FL
24 of 118 Listings
New72$1,189,000
5 bd · 5 ba · 4,999 sqft
17538 Black Rail St, Windermere, FL
Mauro Mateo · KARDOSH REALTY
19$2,190,000
5 bd · 6 ba · 3,582 sqft
6518 Sawyer Shores Ln, Windermere, FL
Daniel Pavel · WRA BUSINESS & REAL ESTATE
41$5,300,000
6 bd · 7 ba · 9,669 sqft
9615 Windy Ridge Rd, Windermere, FL
Traci Cleveland · KELLER WILLIAMS CLASSIC
45$1,050,000
4 bd · 3 ba · 2,984 sqft
5944 Caymus Loop, Windermere, FL
Teresa Stewart · SOUTHERN REALTY GROUP LLC
65$1,348,000
5 bd · 5 ba · 3,835 sqft
7231 Sangalla Dr, Windermere, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
66$2,390,000
5 bd · 5 ba · 4,185 sqft
6544 Cartmel Ln, Windermere, FL
Debora Segnini · FLORIDA CONNEXION PROPERTIES
52$1,598,000
4 bd · 4 ba · 3,751 sqft
6533 Cartmel Ln, Windermere, FL
Carolina Medeiros · PREMIER SOTHEBYS INT'L REALTY
56$1,999,000
4 bd · 4 ba · 3,912 sqft
8229 Tibet Butler Dr, Windermere, FL
Teresa Stewart · SOUTHERN REALTY GROUP LLC
93$4,350,000
5 bd · 5 ba · 5,305 sqft
9602 Maywood Dr, Windermere, FL
Tiphany Weeks · DIAMOND REAL ESTATE GROUP
Open house Sat, Oct 17 · 11:00 AM53$1,280,000
4 bd · 3 ba · 2,441 sqft
104 E 1st Ave, Windermere, FL
Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC
63$8,500,000
4 bd · 5 ba · 7,100 sqft
5092 Isleworth Country Club Dr, Windermere, FL
Michelle Corbin · ISLEWORTH REALTY LLC
100$6,950,000
7 bd · 8 ba · 8,722 sqft
6113 Grosvenor Shore Dr, Windermere, FL
Gwen Flynn · COLDWELL BANKER REALTY
100$3,850,000
4 bd · 6 ba · 6,605 sqft
4906 Aviva Garden Ct, Windermere, FL
Simon Simaan · THE SIMON SIMAAN GROUP
Price Reduced74$2,199,000
4 bd · 6 ba · 4,169 sqft
11532 Waterstone Loop Dr, Windermere, FL
Andrew Kincaid · BHHS FLORIDA REALTY
51$3,595,000
3 bd · 5 ba · 4,333 sqft
9310 Isleworth Gardens Dr, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
74$3,999,000
5 bd · 6 ba · 5,580 sqft
6120 Greatwater Dr, Windermere, FL
Teresa Stewart · SOUTHERN REALTY GROUP LLC
51$1,488,000
4 bd · 4 ba · 3,763 sqft
12721 Jacob Grace Ct, Windermere, FL
Cathy Williams · LAKE NONA REALTY LLC
38$3,250,000
3 bd · 4 ba · 2,848 sqft
6126 Payne Stewart Dr, Windermere, FL
Jill Irwin · IRWIN REALTY GROUP LLC
52$4,395,000
6 bd · 6 ba · 4,739 sqft
5186 Vardon Dr, Windermere, FL
Michelle Corbin · ISLEWORTH REALTY LLC
70$2,995,000
6 bd · 9 ba · 7,321 sqft
13101 Bellaria Cir, Windermere, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
60$7,450,000
7 bd · 10 ba · 8,362 sqft
9343 Tibet Pointe Cir, Windermere, FL
Juliana Jardini Da Cunha Igayara De So · NOVA REAL ESTATE SERVICES INC
51$19,500,000
6 bd · 10 ba · 13,494 sqft
5192 Vardon Dr, Windermere, FL
Jill Irwin · IRWIN REALTY GROUP LLC
63$1,395,000
5 bd · 4 ba · 4,186 sqft
101 Lee St, Windermere, FL
Julie Bettosini, PA · STOCKWORTH REALTY GROUP
13$18,750,000
6 bd · 9 ba · 15,337 sqft
5036 Latrobe Dr, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
Luxury Homes in Windermere, FL: 118 active listings as of .
Stellar MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 97.1% of asking price
Buyers here are paying below asking. MLS · 44 sales · as of Sep 30, 2026