58$1,349,000
4 bd · 4 ba · 2,575 sqft
1939 Woodcrest Dr, Winter Park, FL
Jose Martinez Rivera LLC · LA ROSA REALTY PREMIER LLC
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 339 Listings
58$1,349,000
4 bd · 4 ba · 2,575 sqft
1939 Woodcrest Dr, Winter Park, FL
Jose Martinez Rivera LLC · LA ROSA REALTY PREMIER LLC
New29$305,000
3 bd · 1 ba · 1,216 sqft
2640 Beverly Ave, Winter Park, FL
Celeste Martinez · REAL BROKER, LLC
New16$329,000
3 bd · 2 ba · 1,229 sqft
1740 Puritan Ave, Winter Park, FL
Brenda Brooks · KELLER WILLIAMS REALTY SMART 1
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
44$1,249,000
6 bd · 6 ba · 5,021 sqft
1445 Via Sangro Pl, Winter Park, FL
Kevin Asenjo · COLDWELL BANKER REALTY
New43$750,000
5 bd · 4 ba · 3,496 sqft
8061 Pleasant Pine Cir, Winter Park, FL
Mark Humphreys · RE/MAX ASSURED
Open house Sun, Oct 18 · 12:00 PM30$575,000
3 bd · 3 ba · 2,031 sqft
1931 Aster Dr, Winter Park, FL
Farah Bloom · KELLER WILLIAMS WINTER PARK
NewOpen house Sun, Oct 18 · 12:00 PM37$575,000
4 bd · 2 ba · 1,891 sqft
346 Elkhorn Ct, Winter Park, FL
Natalie Amento · FLORIDA REALTY INVESTMENTS
New70$6,000,000
5 bd · 7 ba · 4,806 sqft
1011 McKean Cir, Winter Park, FL
Clay Wooten · UNITED REAL ESTATE PREFERRED
Open house Sun, Oct 18 · 11:00 AM41$320,000
3 bd · 2 ba · 1,156 sqft
148 Oak Grove Rd, Winter Park, FL
Kelly Althof · CENTRAL FLORIDA REALTY EXPERTS
New25$230,000
3 bd · 2 ba · 1,268 sqft
216 Lewfield Cir #216, Winter Park, FL
Vicki Bray-Fagan, LLC · WATSON REALTY CORP
Open house Sun, Oct 18 · 1:00 PM47$950,000
2 bd · 2 ba · 1,947 sqft
1411 Devon Rd, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
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
41$529,900
4 bd · 2 ba · 1,983 sqft
2174 Shadyhill Ter, Winter Park, FL
Ahmad Karain · SET HOMES REALTY LLC
23$479,999
3 bd · 3 ba · 1,776 sqft
2219 Winter Woods Blvd, Winter Park, FL
Bryan Rhoads · LKV REALTY, LLC
Open house Sun, Oct 18 · 12:00 PM67$3,390,000
5 bd · 7 ba · 4,520 sqft
1751 Glencoe Rd, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
30$575,000
3 bd · 2 ba · 1,804 sqft
1399 Aloma Ave, Winter Park, FL
Nancy Bagby · FANNIE HILLMAN & ASSOCIATES
Open house Sun, Oct 18 · 11:00 AM55$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
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