Open house Sun, Oct 18 · 12:00 PM30$415,900
3 bd · 2 ba · 1,412 sqft
3409 Ferndell Dr, Winter Park, FL
Veronica Lewis · LPT REALTY, LLC
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 338 Listings
Open house Sun, Oct 18 · 12:00 PM30$415,900
3 bd · 2 ba · 1,412 sqft
3409 Ferndell Dr, Winter Park, FL
Veronica Lewis · LPT REALTY, LLC
Open house Sat, Oct 17 · 12:00 PM30$575,000
3 bd · 3 ba · 2,031 sqft
1931 Aster Dr, Winter Park, FL
Farah Bloom · KELLER WILLIAMS WINTER PARK
Open house Sat, Oct 17 · 11:00 AM47$950,000
2 bd · 2 ba · 1,947 sqft
1411 Devon Rd, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
New25$230,000
3 bd · 2 ba · 1,268 sqft
216 Lewfield Cir #216, Winter Park, FL
Vicki Bray-Fagan, LLC · WATSON REALTY CORP
41$529,900
4 bd · 3 ba · 1,983 sqft
2174 Shadyhill Ter, Winter Park, FL
Ahmad Karain · SET HOMES REALTY LLC
NewOpen house Sun, Oct 18 · 2:00 PM42$460,000
3 bd · 3 ba · 2,076 sqft
2356 Shadowland Loop, Winter Park, FL
Lisa Gould · KELLER WILLIAMS WINTER PARK
New23$479,999
3 bd · 3 ba · 1,776 sqft
2219 Winter Woods Blvd, Winter Park, FL
Bryan Rhoads · LKV REALTY, LLC
NewOpen house Sat, Oct 17 · 11:00 AM67$3,390,000
5 bd · 7 ba · 4,520 sqft
1751 Glencoe Rd, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
New30$575,000
3 bd · 2 ba · 1,804 sqft
1399 Aloma Ave, Winter Park, FL
Nancy Bagby · FANNIE HILLMAN & ASSOCIATES
55$985,000
4 bd · 4 ba · 2,916 sqft
1611 Chestnut Ave, Winter Park, FL
Gunel Aydamirli · OLYMPUS EXECUTIVE REALTY INC
20$449,000
3 bd · 2 ba · 1,388 sqft
1320 Buckingham Rd, Winter Park, FL
Matthew Brown · PALLADIUM INVESTMENTS INC
41$2,500,000
5 bd · 5 ba · 3,700 sqft
1760 Oakhurst Ave, Winter Park, FL
Sylvester Harding · SIERRA REALTY GROUP LLC
17$2,295,000
4 bd · 6 ba · 3,295 sqft
2234 Howard Dr, Winter Park, FL
Raquel Elliott · COLDWELL BANKER REALTY
41$491,000
3 bd · 3 ba · 2,308 sqft
1407 Broad Wing Ln, Winter Park, FL
Roger Michaels · R MICHAELS REALTY LLC
14$325,000
3 bd · 3 ba · 1,628 sqft
1462 Siciliano Pt, Winter Park, FL
Selena Rivera · NONA LEGACY POWERED BY LA ROSA
38$1,399,900
4 bd · 4 ba · 2,984 sqft
1737 Indiana Ave, Winter Park, FL
Tori Nguyen · LOKATION
28$185,000
2 bd · 2 ba · 1,281 sqft
4882 Tangerine Ave #4882, Winter Park, FL
Greg Sibley · SIMPLYSOLD REAL ESTATE PREMIER
29$354,000
2 bd · 2 ba · 1,074 sqft
700 Melrose Ave #M23, Winter Park, FL
Linda Jokbengboon · COMPASS FLORIDA LLC
51$519,900
4 bd · 3 ba · 1,842 sqft
731 Bongart Rd, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
25$255,000
2 bd · 2 ba · 1,026 sqft
1500 Gay Rd #26-C, Winter Park, FL
Lianna Dangelo · SOTERA LIVING
Open house Sat, Oct 17 · 12:00 PM46$3,250,000
5 bd · 6 ba · 4,459 sqft
2823 Parkland Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
Open house Sat, Oct 17 · 11:00 AM35$575,000
4 bd · 3 ba · 2,551 sqft
2228 King Charles Ct, Winter Park, FL
Heather Pryor · KELLER WILLIAMS ADVANTAGE REALTY
Price Reduced20$379,900
4 bd · 3 ba · 1,421 sqft
3416 Arbutus Ln, Winter Park, FL
Jorge Schlaefli · GPS REALTY GROUP
Open house Sat, Oct 17 · 11:00 AM90$560,000
4 bd · 2 ba · 2,352 sqft
2067 Poinciana Rd, Winter Park, FL
Brandon Williams · WATSON REALTY CORP
Stellar MLSSource: HJN community data
September 2026
Selling at 97.9% of asking price
Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026