30$175,000
1 bd · 1 ba · 727 sqft
200 St Andrews Blvd #906, Winter Park, FL
Donna Bryant · COLDWELL BANKER REALTY
Homes for Sale in Winter Park, FL
Hide MapHomes for Sale in Winter Park, FL
24 of 342 Listings
30$175,000
1 bd · 1 ba · 727 sqft
200 St Andrews Blvd #906, Winter Park, FL
Donna Bryant · COLDWELL BANKER REALTY
$849,900
4 bd · 3 ba · 2,434 sqft
2011 Harmon Ave, Winter Park, FL
Kim Griffin · RE/MAX EXCLUSIVE COLLECTION
37$410,000
3 bd · 2 ba · 1,300 sqft
1935 Azalea Ave, Winter Park, FL
Michael Cardinali · C BRENNER INC
NewOpen house Sat, Oct 31 · 10:00 AM80$3,995,000
3 bd · 5 ba · 3,885 sqft
125 S Interlachen Ave #4, Winter Park, FL
Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY
Open house Sat, Oct 31 · 11:00 AM13$385,000
3 bd · 2 ba · 1,305 sqft
7361 Grand Ave, Winter Park, FL
Jennifer Sloan · COMPASS FLORIDA LLC
New$1,379,900
4 bd · 4 ba · 2,984 sqft
1534 Miller Ave, Winter Park, FL
Kim Griffin · RE/MAX EXCLUSIVE COLLECTION
New28$225,000
3 bd · 1 ba · 1,227 sqft
3462 Seagrape Dr, Winter Park, FL
Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS
New$249,000
3 bd · 2 ba · 1,345 sqft
4940 Tangerine Ave #4940, Winter Park, FL
Edward Johnston · COLDWELL BANKER REALTY
New16$2,449,000
5 bd · 5 ba · 3,391 sqft
1441 Palm Ave, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
New$1,425,000
4 bd · 5 ba · 3,563 sqft
2237 Woodcrest Dr, Winter Park, FL
Robert St. Pierre · WEEKLEY HOMES REALTY COMPANY
NewOpen house Sat, Oct 31 · 12:00 PM27$365,000
3 bd · 2 ba · 1,208 sqft
2168 Ridge Dr, Winter Park, FL
Uwem Akpan · CHARLES RUTENBERG REALTY ORLANDO
New30$169,999
2 bd · 3 ba · 1,090 sqft
3027 Aaron Bur Ave #L1, Winter Park, FL
Jocelyne Yanez · HOMESMART
New61$1,175,000
3 bd · 3 ba · 2,096 sqft
1500 Harris Cir, Winter Park, FL
Mary Heidrich · COLDWELL BANKER REALTY
Open house Sat, Oct 31 · 1:00 PM39$450,000
5 bd · 3 ba · 1,636 sqft
1825 Chilean Ln, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
NewOpen house Sat, Oct 31 · 12:00 PM44$1,650,000
4 bd · 4 ba · 2,754 sqft
1900 Sunset Dr, Winter Park, FL
Andrea Parra Chopite, PA · FANNIE HILLMAN & ASSOCIATES
Open house Sat, Oct 31 · 12:00 PM69$2,100,000
5 bd · 6 ba · 4,155 sqft
1355 Hibiscus Ave, Winter Park, FL
Nadia Moayeri · PALMANO GROUP RE BROKERAGE LLC
New34$415,000
3 bd · 2 ba · 1,360 sqft
2038 Ponderosa Ave, Winter Park, FL
Stacey Mortensen · KELLER WILLIAMS REALTY AT THE PARKS
New33$440,000
3 bd · 3 ba · 2,308 sqft
1552 Little Wren Ln, Winter Park, FL
Liz Jones · ORANGE SLICE PROPERTIES
New34$550,000
3 bd · 2 ba · 1,610 sqft
257 Lincolnshire Rd, Winter Park, FL
Nick McKee · KELLER WILLIAMS WINTER PARK
New36$1,625,000
3 bd · 3 ba · 2,884 sqft
345 Beloit Ave, Winter Park, FL
Sally Fernandez PA · KELLER WILLIAMS ADVANTAGE III
NewOpen house Fri, Oct 30 · 4:00 PM99$5,695,000
4 bd · 4 ba · 4,725 sqft
541 Virginia Dr, Winter Park, FL
Scott Brazdo · EXP REALTY LLC
34$280,000
2 bd · 2 ba · 1,495 sqft
2352 Sun Valley Cir, Winter Park, FL
Natalie Kauffman · KELLER WILLIAMS CLASSIC
16$375,000
3 bd · 2 ba · 1,674 sqft
1830 Gladiolas Dr, Winter Park, FL
Shelby Kirsch · REAL PROPERTY MANAGEMENT AND REALTY
44$270,000
3 bd · 3 ba · 1,580 sqft
7463 Canford Ct #15, Winter Park, FL
Maria Santana · EXP REALTY LLC
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