New7$4,695,000
11 bd · 8 ba · 3,615 sqft
617 N Interlachen Ave, Winter Park, FL
Greg Owen · EASY REALTY
Luxury Homes in Winter Park, FL
Hide MapLuxury Homes in Winter Park, FL
24 of 108 Listings
New7$4,695,000
11 bd · 8 ba · 3,615 sqft
617 N Interlachen Ave, Winter Park, FL
Greg Owen · EASY REALTY
New76$3,495,000
5 bd · 6 ba · 4,483 sqft
1600 Legion Dr, Winter Park, FL
Brian Teach · COLDWELL BANKER REALTY
New16$2,629,000
5 bd · 5 ba · 3,682 sqft
1681 Woodland Ave, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
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
44$1,249,000
6 bd · 6 ba · 5,021 sqft
1445 Via Sangro Pl, Winter Park, FL
Kevin Asenjo · COLDWELL BANKER REALTY
70$6,000,000
5 bd · 7 ba · 4,806 sqft
1011 McKean Cir, Winter Park, FL
Clay Wooten · UNITED REAL ESTATE PREFERRED
67$3,390,000
5 bd · 7 ba · 4,520 sqft
1751 Glencoe Rd, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
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
38$1,399,900
4 bd · 4 ba · 2,984 sqft
1737 Indiana Ave, Winter Park, FL
Tori Nguyen · LOKATION
46$3,250,000
5 bd · 6 ba · 4,459 sqft
2823 Parkland Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
33$1,150,000
2 bd · 2 ba · 993 sqft
1602 Alabama Dr #107, Winter Park, FL
Valerie Leary · CORCORAN PREMIER REALTY
12$1,699,900
4 bd · 4 ba · 2,661 sqft
2613 Lafayette Ave, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER REALTY
8$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
54$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 Tue, Oct 20 · 12:30 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
73$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
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