33$1,150,000
2 bd · 2 ba · 993 sqft
1602 Alabama Dr #107, Winter Park, FL
Valerie Leary · CORCORAN PREMIER REALTY
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 344 Listings
33$1,150,000
2 bd · 2 ba · 993 sqft
1602 Alabama Dr #107, Winter Park, FL
Valerie Leary · CORCORAN PREMIER REALTY
31$575,000
3 bd · 2 ba · 2,253 sqft
112 Bell Pl, Winter Park, FL
Cara Edwards · ALL REAL ESTATE & INVESTMENTS
New26$329,900
3 bd · 2 ba · 1,216 sqft
4910 Seminole Ave, Winter Park, FL
Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
New12$1,699,900
4 bd · 4 ba · 2,661 sqft
2613 Lafayette Rd, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER REALTY
15$139,999
1 bd · 1 ba · 749 sqft
3032 Antique Oaks Cir #145, Winter Park, FL
Parker Blanchard · OLDE TOWN BROKERS INC
NewOpen house Sat, Oct 10 · 1:00 PM28$675,000
4 bd · 2 ba · 1,650 sqft
2322 Woodcrest Dr, Winter Park, FL
Jill Healey · KELLER WILLIAMS WINTER PARK
29$350,000
3 bd · 2 ba · 1,344 sqft
310 Granada Dr, Winter Park, FL
Milton James · COLDWELL BANKER REALTY
Open house Sat, Oct 10 · 12:00 PM8$2,125,000
5 bd · 5 ba · 3,713 sqft
918 Enclave Pl, Winter Park, FL
Laura Earl · CORCORAN PREMIER REALTY
13$140,000
1 bd · 1 ba · 678 sqft
302 Lewfield Cir #302, Winter Park, FL
Heather Spirazza · REGENCY REAL ESTATE LLC
45$299,000
2 bd · 2 ba · 1,032 sqft
170 Balfour Dr #1, Winter Park, FL
Dana Gold · RE/MAX ASSURED
11$170,000
1 bd · 1 ba · 793 sqft
200 Saint Andrews Blvd #3408, Winter Park, FL
Natalia Moege · PARK 26 REALTY LLC
28$589,900
4 bd · 2 ba · 2,050 sqft
1409 Aster Ct, Winter Park, FL
Jason Price · RE/MAX SELECT GROUP
54$900,000
4 bd · 3 ba · 2,807 sqft
2052 Wood Thrush Ln, Winter Park, FL
Ron Verzaro, II · KELLER WILLIAMS ADVANTAGE REALTY
25$850,000
3 bd · 2 ba · 1,639 sqft
100 S Interlachen Ave #401, Winter Park, FL
Mary Colton · FANNIE HILLMAN & ASSOCIATES
11$3,195,000
5 bd · 6 ba · 4,139 sqft
2119 Howard Dr, Winter Park, FL
Laura Earl · CORCORAN PREMIER REALTY
23$365,000
3 bd · 3 ba · 1,866 sqft
7560 Aloma Pines Ct, Winter Park, FL
Jessica Macias · KELLER WILLIAMS ADVANTAGE III
32$169,900
1 bd · 1 ba · 645 sqft
2500 Lee Rd #123, Winter Park, FL
Scott Sheldon · HOME WISE REALTY GROUP, INC.
25$290,000
2 bd · 3 ba · 1,133 sqft
188 Sandlewood #1, Winter Park, FL
Tom Noelke · NOELKE REALTY
21$399,900
3 bd · 2 ba · 1,247 sqft
5405 Justine Way, Winter Park, FL
Yanira Suarez · LPT REALTY, LLC
14$448,000
3 bd · 1 ba · 1,304 sqft
712 Baffie Ave, Winter Park, FL
George Bateman, III · RP INVESTMENT REALTY LLC
40$159,000
1 bd · 1 ba · 793 sqft
200 Saint Andrews Blvd #704, Winter Park, FL
Alexis Jacobsen · EXP REALTY LLC
15$850,000
4 bd · 3 ba · 2,301 sqft
870 N Phelps Ave, Winter Park, FL
Christina Frucci · RE/MAX TOWN & COUNTRY REALTY
4$1,995,000
4 bd · 4 ba · 3,314 sqft
2007 Edwin Blvd, Winter Park, FL
Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP
21$1,950,000
5 bd · 5 ba · 3,560 sqft
513 Dunraven Dr, Winter Park, FL
Alison Mosley · PREMIER SOTHEBY'S INTL. 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 · 84 sales · as of Sep 30, 2026