Open house Sun, Oct 18 · 2:00 PM42$460,000
3 bd · 3 ba · 2,076 sqft
2356 Shadowland Loop, Winter Park, FL
Lisa Gould · KELLER WILLIAMS WINTER PARK
Townhomes in Winter Park, FL
Hide MapTownhomes in Winter Park, FL
24 of 34 Listings
Open house Sun, Oct 18 · 2:00 PM42$460,000
3 bd · 3 ba · 2,076 sqft
2356 Shadowland Loop, Winter Park, FL
Lisa Gould · KELLER WILLIAMS WINTER PARK
41$491,000
3 bd · 3 ba · 2,308 sqft
1407 Broad Wing Ln, Winter Park, FL
Roger Michaels · R MICHAELS REALTY LLC
14$325,000
3 bd · 3 ba · 1,628 sqft
1462 Siciliano Pt, Winter Park, FL
Selena Rivera · NONA LEGACY POWERED BY LA ROSA
28$169,000
2 bd · 3 ba · 1,031 sqft
3307 Amber Wood Way #106, Winter Park, FL
Bryan Burns · RE/MAX DOWNTOWN
Price Reduced23$355,000
3 bd · 3 ba · 1,866 sqft
7560 Aloma Pines Ct, Winter Park, FL
Jessica Macias · KELLER WILLIAMS ADVANTAGE III
Price Reduced39$355,000
3 bd · 3 ba · 1,872 sqft
7498 Aloma Pines Ct, Winter Park, FL
Marian Coaxum · KELLER WILLIAMS REALTY AT THE PARKS
32$1,300,000
3 bd · 3 ba · 2,563 sqft
504 W Swoope Ave, Winter Park, FL
Jennifer Sloan · COMPASS FLORIDA LLC
Price ReducedOpen house Sun, Oct 18 · 12:00 PM35$275,000
2 bd · 2 ba · 1,544 sqft
2302 Barbados Dr, Winter Park, FL
George Freelove · KELLER WILLIAMS REALTY AT THE PARKS
29$299,990
3 bd · 2 ba · 1,467 sqft
2275 Island Run, Winter Park, FL
Yukey Hoo · U KEY REALTY
36$425,000
3 bd · 3 ba · 1,755 sqft
2349 Shadowland Loop, Winter Park, FL
Lindsey Hudson · REAL BROKER, LLC
20$365,000
3 bd · 3 ba · 1,861 sqft
7506 Cranes Creek Ct #30, Winter Park, FL
Sylvia Marchese · TRANSCONTINENTAL REALTY GROUP,
Price Reduced24$308,900
3 bd · 3 ba · 1,545 sqft
7530 Cranes Creek Ct, Winter Park, FL
Edward Hru · ROO REALTY LLC
Open house Sun, Oct 18 · 1:00 AM67$575,000
2 bd · 3 ba · 1,648 sqft
1259 Indiana Ave, Winter Park, FL
Karan Wienker · COLDWELL BANKER REALTY
Price Reduced28$349,000
3 bd · 3 ba · 1,872 sqft
7605 Aloma Pines Ct, Winter Park, FL
Simon Colak · USCO CAPITAL GROUP
Price Reduced26$399,995
3 bd · 3 ba · 1,782 sqft
2857 Clever Ln, Winter Park, FL
Justin Dalrymple, LLC · MAINFRAME REAL ESTATE
21$660,000
3 bd · 3 ba · 1,690 sqft
1256 Melissa Ct, Winter Park, FL
Wesley Morales · KELLER WILLIAMS REALTY AT THE PARKS
34$575,000
2 bd · 3 ba · 1,851 sqft
1071 Aragon Ave, Winter Park, FL
Greg Vazzana · FANNIE HILLMAN & ASSOCIATES
Price Reduced27$379,998
3 bd · 3 ba · 1,907 sqft
2017 Canny CV, Winter Park, FL
Janice Goulder · KELLER WILLIAMS WINTER PARK
Price Reduced49$915,000
3 bd · 4 ba · 2,093 sqft
1927 S Lakemont Ave, Winter Park, FL
Abby Green · IAD REAL ESTATE
Price Reduced76$3,695,000
3 bd · 5 ba · 3,878 sqft
125 S Interlachen Ave #1, Winter Park, FL
Skip Kirst · COLLADO REAL ESTATE
Price Reduced55$389,000
3 bd · 3 ba · 1,907 sqft
2033 Canny CV, Winter Park, FL
Monica Puche · LPT REALTY, LLC
Price Reduced13$270,000
3 bd · 3 ba · 1,803 sqft
2487 Harbour Way, Winter Park, FL
Joel Garay · LOKATION
Price Reduced41$925,000
3 bd · 3 ba · 2,434 sqft
1138 S Pennsylvania Ave, Winter Park, FL
George Stringer · COLDWELL BANKER REALTY
Price Reduced70$2,695,000
3 bd · 4 ba · 3,286 sqft
660 W Morse Blvd, Winter Park, FL
Jennifer Sloan · COMPASS FLORIDA LLC
Townhomes in Winter Park, FL: 34 active listings as of .
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