37$1,095,000
4 bd · 4 ba · 3,607 sqft
2009 Westover Reserve Blvd, Windermere, FL
Oliver Alfaro · STOCKWORTH REALTY GROUP
Single-Family Homes in Windermere, FL
Hide MapSingle-Family Homes in Windermere, FL
24 of 187 Listings
37$1,095,000
4 bd · 4 ba · 3,607 sqft
2009 Westover Reserve Blvd, Windermere, FL
Oliver Alfaro · STOCKWORTH REALTY GROUP
New73$535,000
4 bd · 3 ba · 2,361 sqft
4936 Wise Bird Dr, Windermere, FL
George Rahi · COLDWELL BANKER REALTY
72$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
42$599,000
3 bd · 2 ba · 1,948 sqft
13125 Penshurst Ln, Windermere, FL
Jason Nagassar · CASTLE REALTY PROFESSIONAL GROUP LLC
41$5,300,000
6 bd · 7 ba · 9,669 sqft
9615 Windy Ridge Rd, Windermere, FL
Traci Cleveland · KELLER WILLIAMS CLASSIC
39$559,000
3 bd · 2 ba · 2,085 sqft
4827 Flint Rd, Windermere, FL
Shelley Dawson · COMPASS FLORIDA LLC
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
28$620,000
4 bd · 4 ba · 2,661 sqft
8576 Powder Ridge Trl, Windermere, FL
Sara Alves Subira · WRA BUSINESS & REAL ESTATE
42$799,000
4 bd · 4 ba · 2,996 sqft
12785 Westside Village Loop, Windermere, FL
Lisa Gould · KELLER WILLIAMS WINTER PARK
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
Price Reduced38$595,000
3 bd · 2 ba · 2,115 sqft
6858 Merrick Landing Blvd, Windermere, FL
Wilfred Sierra Sosa, PA · RE/MAX PRIME PROPERTIES
93$4,350,000
5 bd · 5 ba · 5,305 sqft
9602 Maywood Dr, Windermere, FL
Tiphany Weeks · DIAMOND REAL ESTATE GROUP
65$649,000
4 bd · 3 ba · 2,455 sqft
7030 Mapperton Dr, Windermere, FL
Keith Conklin, LLC · FOLIO REALTY LLC
53$1,280,000
4 bd · 3 ba · 2,441 sqft
104 E 1st Ave, Windermere, FL
Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC
35$950,000
4 bd · 3 ba · 2,680 sqft
8524 Vivaro Isle Way, Windermere, FL
Vincent Cordaro · SERHANT
63$8,500,000
4 bd · 5 ba · 7,100 sqft
5092 Isleworth Country Club Dr, Windermere, FL
Michelle Corbin · ISLEWORTH REALTY LLC
Price Reduced37$860,000
4 bd · 3 ba · 2,704 sqft
11727 Delwick Dr, Windermere, FL
Catherine Lambert PA · BHHS FLORIDA REALTY
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
Single-Family Homes in Windermere, FL: 187 active listings as of .
Stellar MLSSource: HJN community data
September 2026
Selling at 97.0% of asking price
Buyers here are paying below asking. MLS · 45 sales · as of Sep 30, 2026