New25$230,000
3 bd · 2 ba · 1,268 sqft
216 Lewfield Cir #216, Winter Park, FL
Vicki Bray-Fagan, LLC · WATSON REALTY CORP
Homes Under $300K in Winter Park, FL
Hide MapHomes Under $300K in Winter Park, FL
24 of 72 Listings
New25$230,000
3 bd · 2 ba · 1,268 sqft
216 Lewfield Cir #216, Winter Park, FL
Vicki Bray-Fagan, LLC · WATSON REALTY CORP
28$185,000
2 bd · 2 ba · 1,281 sqft
4882 Tangerine Ave #4882, Winter Park, FL
Greg Sibley · SIMPLYSOLD REAL ESTATE PREMIER
25$255,000
2 bd · 2 ba · 1,026 sqft
1500 Gay Rd #26-C, Winter Park, FL
Lianna Dangelo · SOTERA LIVING
28$169,000
2 bd · 3 ba · 1,031 sqft
3307 Amber Wood Way #106, Winter Park, FL
Bryan Burns · RE/MAX DOWNTOWN
Price Reduced15$134,999
1 bd · 1 ba · 749 sqft
3032 Antique Oaks Cir #145, Winter Park, FL
Parker Blanchard · OLDE TOWN BROKERS INC
13$140,000
1 bd · 1 ba · 678 sqft
302 Lewfield Cir #302, Winter Park, FL
Heather Spirazza · REGENCY REAL ESTATE LLC
11$170,000
1 bd · 1 ba · 793 sqft
200 Saint Andrews Blvd #3408, Winter Park, FL
Natalia Moege · PARK 26 REALTY LLC
32$169,900
1 bd · 1 ba · 645 sqft
2500 Lee Rd #123, Winter Park, FL
Scott Sheldon · HOME WISE REALTY GROUP, INC.
25$290,000
2 bd · 3 ba · 1,133 sqft
188 Sandlewood #1, Winter Park, FL
Tom Noelke · NOELKE REALTY
40$159,000
1 bd · 1 ba · 793 sqft
200 Saint Andrews Blvd #704, Winter Park, FL
Alexis Jacobsen · EXP REALTY LLC
24$140,000
2 bd · 1 ba · 881 sqft
1695 Lee Rd #C206, Winter Park, FL
Ingrid Garcia Rodriguez · INVESTMENT REALTY
13$100,000
1 bd · 1 ba · 785 sqft
173 Scottsdale Sq #173, Winter Park, FL
Paola Jimenez · AXEN REALTY, LLC
31$265,000
2 bd · 2 ba · 908 sqft
1250 S Denning Dr #119, Winter Park, FL
Justin McCarthy · FANNIE HILLMAN & ASSOCIATES
16$285,000
3 bd · 2 ba · 1,509 sqft
7348 Grand Ave, Winter Park, FL
Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
20$150,000
2 bd · 2 ba · 1,063 sqft
7453 Daniel Webster Dr #a5, Winter Park, FL
Laila Dkhissi · LA ROSA REALTY PREMIER LLC
19$249,000
3 bd · 3 ba · 1,720 sqft
2463 Grand Teton Cir #2463, Winter Park, FL
Jessica Polanco · MAINFRAME REAL ESTATE
33$299,900
3 bd · 2 ba · 1,078 sqft
5080 Seminole Ave, Winter Park, FL
David Johnston · CREEGAN GROUP
33$234,900
2 bd · 2 ba · 1,295 sqft
2383 Sun Valley Cir #2383, Winter Park, FL
Carmen Aridas · RE/MAX PRIME PROPERTIES
28$170,000
2 bd · 3 ba · 1,031 sqft
7476 Woodburn Ct #38, Winter Park, FL
Habib Fahs · COLDWELL BANKER REALTY
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
18$165,000
2 bd · 2 ba · 840 sqft
3651 N Goldenrod Rd #C109, Winter Park, FL
Valerie Wanzer · REAL ESTATE PROFESSIONALS SE
28$245,000
2 bd · 2 ba · 908 sqft
1250 S Denning Dr #127, Winter Park, FL
Drew Henner · PREMIER SOTHEBY'S INTL. REALTY
29$299,990
3 bd · 2 ba · 1,467 sqft
2275 Island Run, Winter Park, FL
Yukey Hoo · U KEY REALTY
Price Reduced30$255,000
2 bd · 2 ba · 1,008 sqft
5108 Lazy Oaks Dr #5108, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
Homes Under $300K in Winter Park, FL: 72 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