33$359,000
2 bd · 1 ba · 830 sqft
1306 S Pennsylvania Ave #5, Winter Park, FL
Lisa Gould · KELLER WILLIAMS WINTER PARK
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
23 of 351 Listings
33$359,000
2 bd · 1 ba · 830 sqft
1306 S Pennsylvania Ave #5, Winter Park, FL
Lisa Gould · KELLER WILLIAMS WINTER PARK
78$3,495,000
5 bd · 6 ba · 4,478 sqft
662 Granville Drive, Winter Park, FL
Nathalie Bates · PREMIER SOTHEBY'S INTL. REALTY
19$249,000
3 bd · 3 ba · 1,720 sqft
2463 Grand Teton Cir #2463, Winter Park, FL
Jessica Polanco · MAINFRAME REAL ESTATE
Open house Sat, Oct 10 · 12:00 PM50$925,000
4 bd · 3 ba · 2,578 sqft
2572 Fifeshire Dr, Winter Park, FL
MaryAnne Branner · PREMIER SOTHEBY'S INTL. REALTY
49$6,995,000
5 bd · 6 ba · 5,479 sqft
901 Golfview Ter, Winter Park, FL
Mick Night · PREMIER SOTHEBY'S INTL. REALTY
33$299,900
3 bd · 2 ba · 1,078 sqft
5080 Seminole Ave, Winter Park, FL
David Johnston · CREEGAN GROUP
30$699,000
3 bd · 2 ba · 1,450 sqft
250 Carolina Ave #202, Winter Park, FL
Kevin McClanahan · FANNIE HILLMAN & ASSOCIATES
Open house Sat, Oct 3 · 10:00 AM48$1,095,000
4 bd · 4 ba · 2,135 sqft
1517 Harmon Ave, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
24$134,900
2 bd · 2 ba · 756 sqft
7302 Swallow Run #7302, Winter Park, FL
Katie Nguyen · THE NAVY HOUSE
62$850,000
3 bd · 3 ba · 2,488 sqft
2345 Brookshire Ave, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
2$427,000
4 bd · 3 ba · 1,714 sqft
1386 Clematis Ln, Winter Park, FL
Michelle Torrente · ROBERT SLACK LLC
Open house Sun, Oct 4 · 2:00 PM41$675,000
4 bd · 2 ba · 1,688 sqft
2215 Woodcrest Dr, Winter Park, FL
Shari Klafter · KELLER WILLIAMS WINTER PARK
9$5,500,000
5 bd · 7 ba · 5,181 sqft
1166 Palmer Ave, Winter Park, FL
Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY
Open house Sun, Oct 4 · 11:00 AM64$895,000
4 bd · 3 ba · 1,876 sqft
618 Blairshire Cir, Winter Park, FL
Ken Pozek · REAL BROKER, LLC
Open house Sat, Oct 3 · 11:00 AM33$380,000
3 bd · 2 ba · 1,277 sqft
4870 Seminole Ave, Winter Park, FL
Tamara Mazo Ferro · COLDWELL BANKER REALTY
10$1,579,000
4 bd · 4 ba · 2,718 sqft
2417 Chantilly Ave, Winter Park, FL
Amanda Wood · RE/MAX EXCLUSIVE COLLECTION
32$1,300,000
3 bd · 3 ba · 2,563 sqft
504 W Swoope Ave, Winter Park, FL
Jennifer Sloan · COMPASS FLORIDA LLC
Open house Sun, Oct 4 · 12:00 PM61$2,195,000
4 bd · 5 ba · 2,850 sqft
1271 Palmer Ave, Winter Park, FL
JR Keelin · KELLY PRICE & COMPANY LLC
12$960,000
2 bd · 1 ba · 1,290 sqft
447 N Phelps Ave, Winter Park, FL
Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY
Price Reduced28$440,000
4 bd · 2 ba · 2,189 sqft
2301 Conifer Ave, Winter Park, FL
Gregory Buckley · LOKATION
45$2,190,000
4 bd · 3 ba · 3,463 sqft
1803 Barker Dr, Winter Park, FL
Garrett Bell · DENOVO REALTY
46$1,095,000
4 bd · 3 ba · 2,803 sqft
443 Broadview Ave, Winter Park, FL
Nancy Bagby · FANNIE HILLMAN & ASSOCIATES
41$4,400,000
4 bd · 6 ba · 3,720 sqft
702 Via Bella, Winter Park, FL
Mick Night · 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 · 73 sales · as of Sep 29, 2026