4$2,500,000
5 bd · 5 ba · 3,700 sqft
1760 Oakhurst Ave, Winter Park, FL
Sylvester Harding · SIERRA REALTY GROUP LLC
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 343 Listings
4$2,500,000
5 bd · 5 ba · 3,700 sqft
1760 Oakhurst Ave, Winter Park, FL
Sylvester Harding · SIERRA REALTY GROUP LLC
New17$2,295,000
4 bd · 6 ba · 3,295 sqft
2234 Howard Dr, Winter Park, FL
Raquel Elliott · COLDWELL BANKER REALTY
New14$325,000
3 bd · 3 ba · 1,628 sqft
1462 Siciliano Pt, Winter Park, FL
Selena Rivera · NONA LEGACY POWERED BY LA ROSA
New41$491,000
3 bd · 3 ba · 2,308 sqft
1407 Broad Wing Ln, Winter Park, FL
Roger Michaels · R MICHAELS REALTY LLC
New38$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
34$3,250,000
5 bd · 6 ba · 4,459 sqft
2823 Parkland Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
32$575,000
4 bd · 3 ba · 2,551 sqft
2228 King Charles Ct, Winter Park, FL
Heather Pryor · KELLER WILLIAMS ADVANTAGE REALTY
42$745,000
2 bd · 2 ba · 897 sqft
640 N Park Ave #3, Winter Park, FL
Erika Beerbower · FANNIE HILLMAN & ASSOCIATES
Price Reduced20$379,900
4 bd · 3 ba · 1,421 sqft
3416 Arbutus Ln, Winter Park, FL
Jorge Schlaefli · GPS REALTY GROUP
5$210,000
3 bd · 2 ba · 1,043 sqft
2011 Cornell Ave, Winter Park, FL
Jamie L Boone · Federa
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
33$1,150,000
2 bd · 2 ba · 993 sqft
1602 Alabama Dr #107, Winter Park, FL
Valerie Leary · CORCORAN PREMIER REALTY
28$479,900
4 bd · 3 ba · 2,088 sqft
2020 Leanne Ct, Winter Park, FL
Ileana Perez · HOUWZER INC
48$649,000
3 bd · 2 ba · 1,573 sqft
518 Gilbert Rd, Winter Park, FL
Monika Kenney · PALMANO GROUP RE BROKERAGE LLC
28$169,000
2 bd · 3 ba · 1,031 sqft
3307 Amber Wood Way #106, Winter Park, FL
Bryan Burns · RE/MAX DOWNTOWN
27$530,000
3 bd · 2 ba · 1,385 sqft
510 Fitzwalter Dr, Winter Park, FL
Nicole Howell · FANNIE HILLMAN & ASSOCIATES
12$1,699,900
4 bd · 4 ba · 2,661 sqft
2613 Lafayette Ave, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER REALTY
26$329,900
3 bd · 2 ba · 1,216 sqft
4910 Seminole Ave, Winter Park, FL
Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
31$575,000
3 bd · 2 ba · 2,253 sqft
112 Bell Pl, Winter Park, FL
Cara Edwards · ALL REAL ESTATE & INVESTMENTS
15$139,999
1 bd · 1 ba · 749 sqft
3032 Antique Oaks Cir #145, Winter Park, FL
Parker Blanchard · OLDE TOWN BROKERS INC
Georgia MLSStellar 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