72$1,189,000
5 bd · 5 ba · 4,999 sqft
17538 Black Rail St, Windermere, FL
Mauro Mateo · KARDOSH REALTY
5 Bedroom Homes in Windermere, FL
Hide Map5 Bedroom Homes in Windermere, FL
24 of 48 Listings
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
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
93$4,350,000
5 bd · 5 ba · 5,305 sqft
9602 Maywood Dr, Windermere, FL
Tiphany Weeks · DIAMOND REAL ESTATE GROUP
74$3,999,000
5 bd · 6 ba · 5,580 sqft
6120 Greatwater Dr, Windermere, FL
Teresa Stewart · SOUTHERN REALTY GROUP LLC
97$769,000
5 bd · 3 ba · 2,773 sqft
6727 Merrick Landing Blvd, Windermere, FL
Stephanie Demantova Correa · AUTHENTIC REAL ESTATE TEAM
63$1,395,000
5 bd · 4 ba · 4,186 sqft
101 Lee St, Windermere, FL
Julie Bettosini, PA · STOCKWORTH REALTY GROUP
43$689,900
5 bd · 3 ba · 3,006 sqft
6614 Bridgewater Village Rd, Windermere, FL
Khristian Padilla · MY REALTY GROUP, LLC.
81$3,290,000
5 bd · 7 ba · 5,502 sqft
4243 Isabella Cir, Windermere, FL
John Silva · JOHN SILVA REALTY & ASSOCIATES
79$2,685,000
5 bd · 7 ba · 5,747 sqft
8142 Tibet Butler Dr, Windermere, FL
Rob Rahter · STOCKWORTH REALTY GROUP
62$7,200,000
5 bd · 6 ba · 5,993 sqft
5373 Isleworth Country Club Dr, Windermere, FL
Rob Rahter · STOCKWORTH REALTY GROUP
61$2,950,000
5 bd · 4 ba · 7,153 sqft
4301 Down Point Ln, Windermere, FL
Yuliya Mariani · MARIANI REALTY GROUP
Price Reduced70$1,349,900
5 bd · 3 ba · 3,356 sqft
2540 Hempel Cove Ct, Windermere, FL
Tiffany Pantozzi · ALIGN REAL ESTATE LLC
98$2,500,000
5 bd · 5 ba · 4,661 sqft
5526 Marleon Dr, Windermere, FL
Benjamin Attwood · SERHANT
Price Reduced90$3,580,000
5 bd · 7 ba · 5,362 sqft
4302 Isabella Cir, Windermere, FL
Sean Rozanski · JC FLORIDA REALTY LLC
Price Reduced43$1,598,000
5 bd · 5 ba · 4,219 sqft
1480 Hempel Ave, Windermere, FL
Adriana Sanchez · AROD PARTNERS REALTY
29$3,599,000
5 bd · 7 ba · 5,342 sqft
3986 Isabella Cir, Windermere, FL
Ricardo Konageski da Fonseca · WRA BUSINESS & REAL ESTATE
Price Reduced40$939,000
5 bd · 5 ba · 3,797 sqft
9609 Westover Club Cir, Windermere, FL
John Petit · ALPHA R.E. OF CENTRAL FL LLC
Price Reduced33$2,299,000
5 bd · 6 ba · 4,094 sqft
11113 Lake Butler Blvd, Windermere, FL
Stella Freeman · QUATTRO R E SOLUTIONS LLC
95$1,500,000
5 bd · 4 ba · 3,656 sqft
17526 Black Rail St, Windermere, FL
Fernando Zucato · CHARLES RUTENBERG REALTY ORLANDO
Price Reduced82$6,900,000
5 bd · 6 ba · 7,158 sqft
6055 Louise Cove Dr, Windermere, FL
Rob Rahter · STOCKWORTH REALTY GROUP
Price Reduced69$675,000
5 bd · 5 ba · 2,963 sqft
7236 Penkridge Ln, Windermere, FL
Amine Berrada · ATLAS BLUE REALTY INC
65$6,650,000
5 bd · 7 ba · 6,970 sqft
9921 Lake Louise Dr, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
5 Bedroom Homes in Windermere, FL: 48 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