New12$1,699,900
4 bd · 4 ba · 2,661 sqft
2613 Lafayette Rd, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER REALTY
Luxury Homes in Winter Park, FL
Show MapLuxury Homes in Winter Park, FL
23 of 111 Listings
New12$1,699,900
4 bd · 4 ba · 2,661 sqft
2613 Lafayette Rd, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER 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
11$3,195,000
5 bd · 6 ba · 4,139 sqft
2119 Howard Dr, Winter Park, FL
Laura Earl · CORCORAN PREMIER 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
96$2,095,000
4 bd · 4 ba · 3,776 sqft
555 E Lake Sue Ave, Winter Park, FL
Claudia Davidson · KELLER WILLIAMS WINTER PARK
52$6,195,000
5 bd · 6 ba · 5,096 sqft
698 N New York Ave, Winter Park, FL
Mick Night · PREMIER SOTHEBY'S INTL. REALTY
55$1,890,000
4 bd · 4 ba · 3,307 sqft
2614 Parkland Dr, Winter Park, FL
Ryan Gaston · JW GASTON LLC
18$2,990,000
5 bd · 5 ba · 4,050 sqft
532 Langholm Dr, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
Open house Sat, Oct 10 · 1:00 PM39$1,450,000
3 bd · 3 ba · 2,756 sqft
100 S Virginia Ave #201, Winter Park, FL
Tiffany Grindstaff · KELLY PRICE & COMPANY LLC
Open house Sat, Oct 10 · 1:00 PM73$2,089,000
4 bd · 4 ba · 3,479 sqft
1951 Winter Park Rd, Winter Park, FL
Holly Wilton · KELLER WILLIAMS WINTER PARK
34$1,250,000
3 bd · 2 ba · 1,747 sqft
120 Broadview Ave, Winter Park, FL
Catherine D'Amico · FANNIE HILLMAN & ASSOCIATES
31$1,599,000
4 bd · 4 ba · 2,942 sqft
533 Country Club Dr, Winter Park, FL
Jill Healey · KELLER WILLIAMS WINTER PARK
41$3,695,999
4 bd · 5 ba · 3,658 sqft
1742 Temple Dr, Winter Park, FL
Mark Anthony Buot · ROI AVE LLC
78$3,495,000
5 bd · 6 ba · 4,478 sqft
662 Granville Drive, Winter Park, FL
Nathalie Bates · 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
48$1,095,000
4 bd · 4 ba · 2,135 sqft
1517 Harmon Ave, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
13$5,500,000
5 bd · 7 ba · 5,181 sqft
1166 Palmer Ave, Winter Park, FL
Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY
61$2,195,000
4 bd · 5 ba · 2,850 sqft
1271 Palmer Ave, Winter Park, FL
JR Keelin · KELLY PRICE & COMPANY LLC
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
45$2,190,000
4 bd · 3 ba · 3,463 sqft
1803 Barker Dr, Winter Park, FL
Garrett Bell · DENOVO REALTY
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 · 84 sales · as of Sep 30, 2026