New76$3,495,000
5 bd · 6 ba · 4,483 sqft
1600 Legion Dr, Winter Park, FL
Brian Teach · COLDWELL BANKER REALTY
5 Bedroom Homes in Winter Park, FL
Hide Map5 Bedroom Homes in Winter Park, FL
24 of 46 Listings
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
43$750,000
5 bd · 4 ba · 3,496 sqft
8061 Pleasant Pine Cir, Winter Park, FL
Mark Humphreys · RE/MAX ASSURED
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
46$3,250,000
5 bd · 6 ba · 4,459 sqft
2823 Parkland Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. 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
21$1,950,000
5 bd · 5 ba · 3,560 sqft
513 Dunraven Dr, Winter Park, FL
Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY
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
18$2,990,000
5 bd · 5 ba · 4,050 sqft
532 Langholm Dr, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL 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
19$5,500,000
5 bd · 7 ba · 5,181 sqft
1166 Palmer Ave, Winter Park, FL
Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY
7$5,195,900
5 bd · 7 ba · 5,122 sqft
825 Palmer Ave, Winter Park, FL
Laura Earl · CORCORAN PREMIER REALTY
12$1,925,000
5 bd · 4 ba · 3,246 sqft
2260 Mulbry Dr, Winter Park, FL
Alex Bogumil · KONA REALTY SERVICES LLC
25$2,725,000
5 bd · 5 ba · 3,784 sqft
1773 Walnut Ave, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
72$3,395,000
5 bd · 6 ba · 4,015 sqft
160 W Rockwood Way, Winter Park, FL
Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced69$775,000
5 bd · 4 ba · 2,840 sqft
1164 Dodd Road, Winter Park, FL
Michael John Rothenburg · Charles Rutenberg Realty FTL
66$3,265,000
5 bd · 6 ba · 4,949 sqft
1761 Legion Dr, Winter Park, FL
Harry Pool, III · COLDWELL BANKER REALTY
Price Reduced39$419,990
5 bd · 3 ba · 1,442 sqft
2181 Linden Rd, Winter Park, FL
Paula Chavez · KELLER WILLIAMS ADVANTAGE III
40$860,000
5 bd · 4 ba · 3,284 sqft
120 Longbranch Rd, Winter Park, FL
Karen Albright · OPENDOOR BROKERAGE LLC
5$2,700,000
5 bd · 5 ba · 3,588 sqft
648 Worthington Dr, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
5 Bedroom Homes in Winter Park, FL: 46 active listings as of .
BeachesMLSStellar 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