Open house Sat, Oct 3 · 2:00 AM10$1,829,000
4 bd · 4 ba · 2,706 sqft
1550 Palm Ave, Winter Park, FL
Brian Mitnik · RE/MAX 200 REALTY
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 350 Listings
Open house Sat, Oct 3 · 2:00 AM10$1,829,000
4 bd · 4 ba · 2,706 sqft
1550 Palm Ave, Winter Park, FL
Brian Mitnik · RE/MAX 200 REALTY
72$1,350,000
6 bd · 6 ba · 5,021 sqft
1445 Via Sangro Pl, Winter Park, FL
Suzanne Seenandan · PREFERRED RE BROKERS III
31$660,000
4 bd · 4 ba · 1,840 sqft
1016 Aragon Ave, Winter Park, FL
Pam Stewart · PALMANO GROUP RE BROKERAGE LLC
41$285,000
2 bd · 3 ba · 960 sqft
283 Sandlewood Trl #3, Winter Park, FL
Crystal Adams, PA · RE/MAX INNOVATION
Price Reduced39$419,990
5 bd · 3 ba · 1,442 sqft
2181 Linden Rd, Winter Park, FL
Paula Chavez · KELLER WILLIAMS ADVANTAGE III
Price Reduced21$1,449,000
3 bd · 3 ba · 2,080 sqft
150 E Reading Way, Winter Park, FL
Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES
Price Reduced27$620,000
3 bd · 1 ba · 1,243 sqft
1416 Border Dr, Winter Park, FL
Audra Wilks · PREMIER SOTHEBY'S INTL. REALTY
Price ReducedOpen house Sun, Oct 4 · 12:00 PM31$664,000
3 bd · 3 ba · 1,794 sqft
900 Carver St, Winter Park, FL
Farhad Haniff · EXP REALTY LLC
Price Reduced28$349,000
3 bd · 3 ba · 1,872 sqft
7605 Aloma Pines Ct, Winter Park, FL
Simon Colak · USCO CAPITAL GROUP
Price Reduced39$925,000
2 bd · 2 ba · 1,763 sqft
311 E Morse Blvd #4-5, Winter Park, FL
Kim Garcia · KELLER WILLIAMS ADVANTAGE REALTY
Price ReducedOpen house Sun, Oct 4 · 11:00 AM38$575,000
4 bd · 2 ba · 1,936 sqft
7525 Lodge Pole Trl, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
Price Reduced36$194,900
2 bd · 2 ba · 1,037 sqft
623 Grenadine Ct #623, Winter Park, FL
Carolyn Kickhofel · COLDWELL BANKER REALTY
25$147,000
1 bd · 1 ba · 678 sqft
285 Lewfield Cir #285, Winter Park, FL
Millie Soto · COLDWELL BANKER REALTY
Open house Sun, Oct 4 · 2:00 PM35$899,000
3 bd · 3 ba · 2,022 sqft
1621 Chestnut Ave, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC
Price Reduced16$143,500
1 bd · 1 ba · 749 sqft
3019 Antique Oaks Cir #127, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
Price Reduced55$650,000
4 bd · 3 ba · 2,067 sqft
943 Fairway Dr, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
16$799,000
3 bd · 3 ba · 1,957 sqft
1278 S Pennsylvania Ave #13, Winter Park, FL
Nancy Merriam · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced26$399,995
3 bd · 3 ba · 1,782 sqft
2857 Clever Ln, Winter Park, FL
Justin Dalrymple, LLC · MAINFRAME REAL ESTATE
Price Reduced37$495,000
3 bd · 2 ba · 2,047 sqft
1660 Gladiolas Dr, Winter Park, FL
Stephen Hachey · FLAT FEE MLS REALTY
40$860,000
5 bd · 4 ba · 3,284 sqft
120 Longbranch Rd, Winter Park, FL
Karen Albright · OPENDOOR BROKERAGE LLC
21$660,000
3 bd · 3 ba · 1,690 sqft
1256 Melissa Ct, Winter Park, FL
Wesley Morales · KELLER WILLIAMS REALTY AT THE PARKS
28$419,000
4 bd · 2 ba · 1,836 sqft
1842 Puritan Ave, Winter Park, FL
Karan Jodha · MOBED REALTY, P.A.
Price Reduced37$525,000
4 bd · 2 ba · 2,126 sqft
2641 Carvell Ct, Winter Park, FL
Christina Perez · CHAMBERLAIN REALTY LLC
86$739,000
2 bd · 2 ba · 1,311 sqft
250 Carolina Ave #205, Winter Park, FL
Troy Hensley · BHHS FLORIDA REALTY
Stellar MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 97.9% of asking price
Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026