29$299,990
3 bd · 2 ba · 1,467 sqft
2275 Island Run, Winter Park, FL
Yukey Hoo · U KEY REALTY
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 351 Listings
29$299,990
3 bd · 2 ba · 1,467 sqft
2275 Island Run, Winter Park, FL
Yukey Hoo · U KEY REALTY
Price Reduced54$1,095,000
3 bd · 3 ba · 1,873 sqft
1922 Hammerlin Ave, Winter Park, FL
Felicia Donatelli · PALM PROPERTIES OF CF, INC.
36$425,000
3 bd · 3 ba · 1,755 sqft
2349 Shadowland Loop, Winter Park, FL
Lindsey Hudson · REAL BROKER, LLC
18$130,000
1 bd · 1 ba · 645 sqft
2500 Lee Rd #143, Winter Park, FL
Carol Wittman · PALMANO GROUP RE BROKERAGE LLC
33$1,350,000
4 bd · 4 ba · 2,998 sqft
1320 Orchid Ave, Winter Park, FL
Isis Sarcos · EXP REALTY LLC
Price Reduced58$1,295,000
3 bd · 4 ba · 2,191 sqft
720 Pansy Ave, Winter Park, FL
Nick McKee · KELLER WILLIAMS WINTER PARK
48$739,777
4 bd · 2 ba · 2,267 sqft
4039 Cool Water Ct, Winter Park, FL
Karen Arbutine · RE/MAX CENTRAL REALTY
Price Reduced11$159,900
2 bd · 2 ba · 840 sqft
3651 N Goldenrod Rd #C205, Winter Park, FL
Hitesh Khatri · CFRP REALTY LLC
20$365,000
3 bd · 3 ba · 1,861 sqft
7506 Cranes Creek Ct #30, Winter Park, FL
Sylvia Marchese · TRANSCONTINENTAL REALTY GROUP,
Open house Sun, Oct 4 · 2:00 PM31$725,000
3 bd · 2 ba · 1,563 sqft
1850 Bryan Ave, Winter Park, FL
Jennifer King · CORCORAN PREMIER REALTY
24$309,900
3 bd · 3 ba · 1,545 sqft
7530 Cranes Creek Ct, Winter Park, FL
Edward Hru · ROO REALTY LLC
30$269,000
2 bd · 2 ba · 1,008 sqft
5108 Lazy Oaks Dr #5108, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
Price Reduced40$529,000
4 bd · 2 ba · 1,845 sqft
2211 King Richards Ct, Winter Park, FL
Nicole Howell · FANNIE HILLMAN & ASSOCIATES
Open house Sat, Oct 3 · 1:00 PM67$575,000
2 bd · 3 ba · 1,648 sqft
1259 Indiana Ave, Winter Park, FL
Karan Wienker · COLDWELL BANKER REALTY
Price Reduced49$999,500
3 bd · 2 ba · 1,487 sqft
1220 Howell Branch Rd, Winter Park, FL
Fook Snipper · PARK PLACE REAL ESTATE
25$269,000
2 bd · 1 ba · 710 sqft
151 N Orlando Ave #242, Winter Park, FL
Alexander Scures · COLONIALTOWN REALTY
Price Reduced27$950,000
4 bd · 3 ba · 2,528 sqft
471 Holt Ave, Winter Park, FL
Tina Bollet · FLORIDA HOME TEAM REALTY LLC
Price Reduced17$269,900
3 bd · 2 ba · 1,197 sqft
3302 Royal St, Winter Park, FL
Robert Arnold, Jr · SAND DOLLAR REALTY GROUP INC
Open house Sat, Oct 3 · 11:00 AM64$1,598,000
4 bd · 4 ba · 2,916 sqft
2430 Chantilly Ave, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC
47$1,600,000
3 bd · 3 ba · 2,733 sqft
2207 Kindel Ave, Winter Park, FL
Sandra Velasquez · THE SIMON SIMAAN GROUP
66$3,265,000
5 bd · 6 ba · 4,949 sqft
1761 Legion Dr, Winter Park, FL
Harry Pool, III · COLDWELL BANKER REALTY
44$1,950,000
3 bd · 4 ba · 2,703 sqft
751 Pansy Ave, Winter Park, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
31$245,000
2 bd · 2 ba · 913 sqft
1250 S Denning Dr #Unit 233, Winter Park, FL
Samuel Kingsford · STOCKWORTH REALTY GROUP
47$189,900
2 bd · 2 ba · 953 sqft
222 Lewfield Cir, Winter Park, FL
Joshua Neudigate · MARKET CONNECT REALTY LLC
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