Price Reduced51$4,999,500
4 bd · 5 ba · 4,330 sqft
5138 Fairway Oaks Dr, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
Homes for Sale in Windermere, FL
Hide MapHomes for Sale in Windermere, FL
24 of 223 Listings
Price Reduced51$4,999,500
4 bd · 5 ba · 4,330 sqft
5138 Fairway Oaks Dr, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
Price Reduced73$979,990
4 bd · 3 ba · 2,740 sqft
14353 Crest Palm Ave, Windermere, FL
Cindy Sapp · OLYMPUS EXECUTIVE REALTY INC
Price Reduced65$2,290,000
6 bd · 4 ba · 4,482 sqft
9648 Weatherstone Ct, Windermere, FL
Andy Neal · THE AGENCY FL
Price Reduced65$1,395,000
4 bd · 5 ba · 3,399 sqft
12411 Montalcino Cir, Windermere, FL
Mauro Costa · WILLIAM RAVEIS FLORIDA, LLC
Price Reduced56$1,375,000
5 bd · 4 ba · 3,487 sqft
12718 Windermere Isles Pl, Windermere, FL
Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO
Price Reduced30$584,900
4 bd · 2 ba · 2,050 sqft
9011 Chapman Oak Ct, Windermere, FL
Shiran Moyal · TOWNE CENTER REALTY
68$15,500,000
10 bd · 17 ba · 13,425 sqft
12488 Park Ave, Windermere, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
Price Reduced44$1,089,000
4 bd · 3 ba · 3,390 sqft
715 Magnolia St, Windermere, FL
Robert Trien · IRIS INTERNATIONAL
Price Reduced55$725,000
4 bd · 4 ba · 2,742 sqft
910 Lascala Dr, Windermere, FL
Petra Bukalo PA · FLORIDA REALTY INVESTMENTS
Price Reduced63$4,100,000
3 bd · 5 ba · 5,004 sqft
9144 Isleworth Gardens Dr, Windermere, FL
Megan Dowdy · MEGAN DOWDY REALTY, LLC
Price Reduced40$549,000
4 bd · 3 ba · 2,411 sqft
4627 Blue Major Dr, Windermere, FL
Daniel DeLuca · DENIZ REALTY PARTNERS LLC
76$1,130,000
8 bd · 5 ba · 4,830 sqft
6152 Golden Dewdrop Trl, Windermere, FL
Vitor Silva · VESTI LLC
Price Reduced26$449,000
3 bd · 3 ba · 1,531 sqft
7327 Millstone St, Windermere, FL
Storm Miller · COMPASS FLORIDA LLC
Price Reduced44$989,990
4 bd · 4 ba · 3,153 sqft
14371 Crest Palm Ave, Windermere, FL
Cindy Sapp · OLYMPUS EXECUTIVE REALTY INC
Price Reduced44$749,995
3 bd · 2 ba · 2,469 sqft
9237 Sabal Palm Cir, Windermere, FL
Chelsea Murphy · OLYMPUS EXECUTIVE REALTY INC
24$399,000
2 bd · 3 ba · 1,429 sqft
12405 Cruxbury Dr, Windermere, FL
Steve Lang · HOMEVEST REALTY
Price Reduced26$460,000
3 bd · 3 ba · 1,974 sqft
12353 Via Derna Pl, Windermere, FL
Nathalya Ferreira da Silva · AUTHENTIC REAL ESTATE TEAM
Price Reduced31$780,000
4 bd · 4 ba · 3,124 sqft
5413 Walsh Pond Ct, Windermere, FL
Brenda Jebailey · HAVEN PROPERTY GROUP LLC
Price Reduced30$629,900
3 bd · 2 ba · 2,147 sqft
13622 Darchance Rd, Windermere, FL
Javin Lopez · AVANTI WAY REALTY LLC
Price Reduced57$3,800,000
4 bd · 5 ba · 5,301 sqft
5151 Latrobe Dr, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
Price Reduced44$455,000
3 bd · 3 ba · 2,091 sqft
13755 Bravante Aly, Windermere, FL
Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS
Price Reduced10$850,000
4 bd · 3 ba · 2,224 sqft
13542 Gorgona Isle Dr, Windermere, FL
Thiago De Ataide · WRA BUSINESS & REAL ESTATE
27$915,000
4 bd · 3 ba · 2,988 sqft
9150 Outlook Rock Trl, Windermere, FL
Andrea Munoz · MOSAIC PARTNERS GROUP
100$1,490,000
5 bd · 4 ba · 3,492 sqft
11339 Camden Park Dr, Windermere, FL
Martonio Pinto · AMERICAN HORIZONS REALTY
Stellar MLSSource: HJN community data
August 2026
Selling at 95.7% of asking price
Buyers here are paying below asking. MLS · 54 sales · as of Aug 31, 2026