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Recently Sold Homes in Winter Park, FL

902 homes

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SOLD
APR 27, 2026
$275,000
2 Beds
2 Baths
1,020 sqft
2612 EXUMA WAY,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE REALTY
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SOLD
APR 27, 2026
$435,800
3 Beds
2 Baths
1,560 sqft
5418 ARDMORE DRIVE,
Winter Park, FL 32792
WEMERT GROUP REALTY LLC
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SOLD
APR 24, 2026
$865,000
3 Beds
2.5 Baths
2,114 sqft
628 DUNBLANE DRIVE,
Winter Park, FL 32792
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 24, 2026
$409,000
3 Beds
2 Baths
1,670 sqft
4048 Waterview Loop,
Winter Park, FL 32792
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SOLD
APR 24, 2026
$105,000
2 Beds
1 Bath
881 sqft
1695 LEE ROAD #C214,
Winter Park, FL 32789
PROFESSIONAL REAL ESTATE TEAM
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SOLD
APR 24, 2026
$300,000
1 Bed
1 Bath
570 sqft
311 E MORSE BOULEVARD #6-3,
Winter Park, FL 32789
FLORIDA ONE REAL ESTATE LLC
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SOLD
APR 23, 2026
$145,000
1 Bed
1 Bath
645 sqft
2500 LEE ROAD #243,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
SOLD
APR 23, 2026
$490,000
3 Beds
2 Baths
1,745 sqft
2126 N HAMPTON CIRCLE,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
APR 23, 2026
$129,300
2 Beds
2 Baths
1,058 sqft
4812 Tangerine Ave #4812,
Winter Park, FL 32792
SOLD
APR 22, 2026
$1,600,000
4 Beds
2.5 Baths
3,263 sqft
446 ALBERTA DRIVE,
Winter Park, FL 32789
CHARLES RUTENBERG REALTY ORLANDO
SOLD
APR 22, 2026
$545,000
4 Beds
2 Baths
1,948 sqft
2814 SHERIFF WAY,
Winter Park, FL 32792
CORCORAN PREMIER REALTY
SOLD
APR 22, 2026
$5,650,000
Studio
11,034 sqft
2451 Howell Market Ln,
Winter Park, FL 32792
SOLD
APR 21, 2026
$163,000
2 Beds
2.5 Baths
1,031 sqft
3262 OAK LAKE PLACE #139,
Winter Park, FL 32792
FLORIDA PRESTIGIOUS HOMES INC
SOLD
APR 21, 2026
$385,000
3 Beds
2.5 Baths
1,755 sqft
2232 SHADOWLAND LOOP,
Winter Park, FL 32792
U S GLORY REALTY
SOLD
APR 20, 2026
$172,000
2 Beds
2 Baths
1,068 sqft
7733 Country Pl,
Winter Park, FL 32792
SOLD
APR 20, 2026
$189,900
2 Beds
2 Baths
953 sqft
102 Lewfield Cir,
Winter Park, FL 32792
SOLD
APR 17, 2026
$372,400
4 Beds
1.5 Baths
1,248 sqft
770 CARVER STREET,
Winter Park, FL 32789
LEGENDS REALTY
SOLD
APR 17, 2026
$675,000
4 Beds
2 Baths
2,068 sqft
620 Darcey Dr,
Winter Park, FL 32792
SOLD
APR 17, 2026
$649,000
4 Beds
2 Baths
1,936 sqft
1523 GOLFSIDE DRIVE,
Winter Park, FL 32792
BALDWIN PARK REALTY LLC
SOLD
APR 17, 2026
$2,232,000
3 Beds
3.5 Baths
2,714 sqft
660 Osceola Ave 101,
Winter Park, FL 32789
FLORIDA ONE REAL ESTATE LLC
SOLD
APR 17, 2026
$110,000
3 Beds
2 Baths
1,149 sqft
1695 Lee Rd,
Winter Park, FL 32789
SOLD
APR 16, 2026
$630,000
4 Beds
2 Baths
1,943 sqft
649 BERWICK DRIVE,
Winter Park, FL 32792
MAINFRAME REAL ESTATE
SOLD
APR 16, 2026
$1,100,000
2 Beds
2 Baths
1,402 sqft
1602 ALABAMA DRIVE #403,
Winter Park, FL 32789
CORCORAN PREMIER REALTY
SOLD
APR 15, 2026
$1,100,000
2 Beds
2 Baths
1,220 sqft
100 S INTERLACHEN AVENUE #404,
Winter Park, FL 32789
COLDWELL BANKER REALTY
SOLD
APR 15, 2026
$1,500,000
4 Beds
4.5 Baths
3,022 sqft
132 BURKS CIRCLE,
Winter Park, FL 32789
KELLER WILLIAMS REALTY AT THE PARKS
SOLD
APR 15, 2026
$1,850,000
4 Beds
4 Baths
3,670 sqft
1713 ELIZABETHS WALK,
Winter Park, FL 32789
RE/MAX TOWN & COUNTRY REALTY
SOLD
APR 15, 2026
$189,900
2 Beds
2 Baths
953 sqft
102 LEWFIELD CIRCLE #102,
Winter Park, FL 32792
UNITED REALTY GROUP INC
SOLD
APR 15, 2026
$172,000
2 Beds
2 Baths
1,068 sqft
7733 COUNTRY PLACE #G2,
Winter Park, FL 32792
WEMERT GROUP REALTY LLC
SOLD
APR 15, 2026
$110,000
2 Beds
1 Bath
881 sqft
1695 LEE ROAD #E211,
Winter Park, FL 32789
KELLER WILLIAMS REALTY SMART 1
SOLD
APR 14, 2026
$430,000
3 Beds
2.5 Baths
1,756 sqft
1375 MERRYDALE WAY,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
APR 13, 2026
$610,000
1860 STAUNTON AVENUE,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
APR 13, 2026
$3,100,001
5 Beds
4.5 Baths
4,686 sqft
611 WILLIAMS DRIVE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 13, 2026
$365,000
3 Beds
2 Baths
1,552 sqft
5097 Lake Howell Rd,
Winter Park, FL 32792
SOLD
APR 13, 2026
$376,000
3 Beds
2 Baths
1,424 sqft
3324 BALSAM DRIVE,
Winter Park, FL 32792
KELLER WILLIAMS REALTY AT THE PARKS
SOLD
APR 13, 2026
$800,000
4 Beds
3.5 Baths
3,020 sqft
1183 WILDMEADOW RUN,
Winter Park, FL 32792
COLDWELL BANKER REALTY
SOLD
APR 10, 2026
$620,000
2 Beds
1.5 Baths
1,149 sqft
1137 OAKS BOULEVARD,
Winter Park, FL 32789
RE/MAX 200 REALTY
SOLD
APR 10, 2026
$1,905,000
5 Beds
4.5 Baths
3,746 sqft
501 HENKEL CIRCLE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 10, 2026
$501,000
2 Beds
2 Baths
1,683 sqft
1289 HARMON AVENUE,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
SOLD
APR 10, 2026
$560,000
4 Beds
3.5 Baths
2,035 sqft
1517 HARMON AVENUE,
Winter Park, FL 32789
STELLAR NON-MEMBER OFFICE
SOLD
APR 10, 2026
$200,000
2 Beds
1 Bath
818 sqft
1996 INDIANA AVENUE,
Winter Park, FL 32789
RE/MAX 200 REALTY

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511