26$599,000
3 bd · 2 ba · 2,031 sqft
4026 Tenita Dr, Winter Park, FL
Ruby Davis · RUBY DAVIS, BROKER
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 351 Listings
26$599,000
3 bd · 2 ba · 2,031 sqft
4026 Tenita Dr, Winter Park, FL
Ruby Davis · RUBY DAVIS, BROKER
Price Reduced27$379,999
3 bd · 3 ba · 1,907 sqft
2017 Canny CV, Winter Park, FL
Janice Goulder · KELLER WILLIAMS WINTER PARK
28$495,000
3 bd · 2 ba · 1,380 sqft
5316 Halyard Ct, Winter Park, FL
Neil Chetram · LA ROSA REALTY CW PROPERTIES L
Price Reduced11$214,900
3 bd · 3 ba · 1,151 sqft
7413 Belle River Ct #3, Winter Park, FL
Ivan Tobon · OUTLET REALTY
Price Reduced92$985,000
4 bd · 3 ba · 2,868 sqft
2667 Cochise Trl, Winter Park, FL
Beverley Kistler · COLDWELL BANKER REALTY
Price ReducedOpen house Sat, Oct 3 · 12:00 PM48$915,000
3 bd · 4 ba · 2,093 sqft
1927 S Lakemont Ave, Winter Park, FL
Abby Green · IAD REAL ESTATE
19$510,000
3 bd · 3 ba · 1,669 sqft
1061 Aragon Ave #1061, Winter Park, FL
Lois Ann Cox, PA · WATSON REALTY CORP
76$3,895,000
3 bd · 5 ba · 3,878 sqft
125 S Interlachen Ave #1, Winter Park, FL
Skip Kirst · COLLADO REAL ESTATE
Price Reduced15$105,000
1 bd · 1 ba · 796 sqft
1000 S Semoran Blvd #302, Winter Park, FL
Amaal Barakat · KELLER WILLIAMS ADVANTAGE III
10$1,749,000
4 bd · 4 ba · 2,715 sqft
2525 Lafayette Ave, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER REALTY
12$2,299,000
5 bd · 5 ba · 2,868 sqft
1840 Laurel Rd, Winter Park, FL
Matt Tomaszewski · CORCORAN PREMIER REALTY
Price Reduced36$669,900
3 bd · 2 ba · 1,800 sqft
433 Gilbert Rd, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
Price Reduced29$268,000
2 bd · 2 ba · 1,295 sqft
2475 Tahoe Cir, Winter Park, FL
Sarah Doyer · COLDWELL BANKER REALTY
Price Reduced35$430,000
3 bd · 2 ba · 1,645 sqft
3740 Hawthorne Ln, Winter Park, FL
John Crea · FLORIDA REALTY INVESTMENTS
Price Reduced48$1,449,000
5 bd · 5 ba · 3,109 sqft
777 Halifax Ave, Winter Park, FL
Jared Smith · SAFFORD REAL ESTATE LLC
29$425,000
3 bd · 2 ba · 1,238 sqft
1886 Clematis Ln, Winter Park, FL
Steven Greening · EXP REALTY LLC
Price Reduced15$410,000
3 bd · 2 ba · 1,483 sqft
5409 Albert Dr, Winter Park, FL
Raul Pino · SOVEREIGN REAL ESTATE GROUP
Price Reduced27$334,000
3 bd · 2 ba · 1,149 sqft
3562 Bougainvillea Dr, Winter Park, FL
Tania Crandall · SHORESTONE PROPERTY GROUP
Price Reduced29$798,000
5 bd · 4 ba · 2,832 sqft
724 Monmouth Way, Winter Park, FL
Cardiff Howell · CENTRAL TOWER PROPERTIES
Price Reduced22$115,000
1 bd · 1 ba · 735 sqft
1000 S Semoran Blvd #305, Winter Park, FL
Melissa Vance · MAINFRAME REAL ESTATE
Price ReducedOpen house Sun, Oct 4 · 11:00 AM54$464,000
3 bd · 2 ba · 1,737 sqft
2703 Tierra Cir, Winter Park, FL
Tony Ubaldini · EXP REALTY LLC
Price Reduced55$389,000
3 bd · 3 ba · 1,907 sqft
2033 Canny CV, Winter Park, FL
Monica Puche · LPT REALTY, LLC
49$1,800,000
5 bd · 5 ba · 4,029 sqft
281 Brewer Ave, Winter Park, FL
John Henthorn · HENTHORN REAL ESTATE
Price Reduced25$395,000
3 bd · 2 ba · 1,201 sqft
2568 Lotafun Ave, Winter Park, FL
Randall Wolber, Jr · SIMPLE FEE LISTINGS 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