Price Reduced42$579,000
3 bd · 2 ba · 1,706 sqft
13231 Roxboro Rd, Windermere, FL
Shannon Tichenor · LA ROSA REALTY KISSIMMEE
Homes for Sale in Windermere, FL
Show MapHomes for Sale in Windermere, FL
24 of 224 Listings
Price Reduced42$579,000
3 bd · 2 ba · 1,706 sqft
13231 Roxboro Rd, Windermere, FL
Shannon Tichenor · LA ROSA REALTY KISSIMMEE
Price Reduced49$438,000
4 bd · 3 ba · 1,631 sqft
8386 Iron Mountain Trl, Windermere, FL
Hilda Teran Nava · MY REALTY GROUP, LLC.
Price Reduced28$740,000
5 bd · 4 ba · 2,989 sqft
8931 Lookout Pointe Dr, Windermere, FL
Lilly Vazquez · SPECIALIZED PROPERTY MANAGEMENT
78$5,999,000
5 bd · 5 ba · 5,511 sqft
800 W 2nd Ave, Windermere, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
99$2,800,000
6 bd · 8 ba · 6,781 sqft
13250 Bellaria Cir, Windermere, FL
Scarllet Lettre · CHARLES RUTENBERG REALTY INC
100$1,595,000
4 bd · 4 ba · 3,166 sqft
12417 Montalcino Cir, Windermere, FL
Aziz Elbrak · LA ROSA REALTY LLC
Price Reduced37$350,000
3 bd · 3 ba · 1,644 sqft
7712 Fordson Ln, Windermere, FL
Jorge Martinez, Jr · KELLER WILLIAMS CLASSIC
Price Reduced30$659,000
4 bd · 4 ba · 2,610 sqft
7537 Brofield Ave, Windermere, FL
Ping Song · SUNSHINE GROUP USA, INC
Price Reduced44$1,065,000
4 bd · 4 ba · 3,646 sqft
8344 Bowden Way, Windermere, FL
Immu Korvenmaa · ALIGN REAL ESTATE LLC
97$15,900,000
8 bd · 11 ba · 14,068 sqft
6119 Grosvenor Shore Dr, Windermere, FL
Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced40$439,000
4 bd · 3 ba · 1,910 sqft
11429 Brownstone St, Windermere, FL
Jenny Wemert · WEMERT GROUP REALTY LLC
35$330,000
2 bd · 3 ba · 1,232 sqft
14030 Sparkling Cove Ln #603, Windermere, FL
Shane Jordan · COLDWELL BANKER REALTY
89$2,500,000
6 bd · 4 ba · 4,858 sqft
1629 Hempel Ave, Windermere, FL
Mike Borah · COLDWELL BANKER REALTY
Price Reduced37$539,900
3 bd · 2 ba · 1,819 sqft
9433 Palm Tree Dr, Windermere, FL
Kitty Mark · COLDWELL BANKER REALTY
Price Reduced53$798,000
5 bd · 5 ba · 3,373 sqft
4642 River Gem Ave, Windermere, FL
John Silva · JOHN SILVA REALTY & ASSOCIATES
93$6,700,000
8 bd · 10 ba · 8,133 sqft
8342 Boyla Ct, Windermere, FL
Simon Simaan · THE SIMON SIMAAN GROUP
Price Reduced43$1,150,000
4 bd · 3 ba · 3,540 sqft
2009 Woody Dr, Windermere, FL
Rebekkah Boskovich · REVEL REALTY LLC
Price Reduced65$980,000
4 bd · 3 ba · 3,478 sqft
2512 Tryon Pl, Windermere, FL
Jamie Stolinas Crame, LLC · CENTURY 21 CARIOTI
34$444,900
3 bd · 3 ba · 1,642 sqft
7060 Ventnor Dr, Windermere, FL
Lidia Barberini · AGENT TRUST REALTY CORPORATION
Price Reduced32$325,000
3 bd · 2 ba · 1,442 sqft
11446 Jasper Kay Ter #103, Windermere, FL
Jay Stewart · SOUTHERN REALTY GROUP LLC
Price Reduced31$555,000
3 bd · 2 ba · 1,706 sqft
13219 Charfield St, Windermere, FL
Patricia Schraiber · DENIZ REALTY PARTNERS LLC
Price Reduced48$550,000
3 bd · 2 ba · 1,948 sqft
13137 Penshurst Ln, Windermere, FL
Jauquese Knowles · MORRIS WILLIAMS REALTY
Price Reduced55$1,900,000
4 bd · 6 ba · 5,515 sqft
1238 Lake Whitney Dr, Windermere, FL
Jason Crane · JASON CRANE REAL ESTATE LLC
73$6,500,000
5 bd · 7 ba · 5,471 sqft
9316 Gladys Garden Ct, Windermere, FL
Monica Lochmandy · ISLEWORTH REALTY LLC
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