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Recently Sold Homes in Winter Park, FL

908 homes

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SOLD
JUN 29, 2026
$285,000
2 Beds
2 Baths
1,241 sqft
3159 GREENWOOD STREET,
Winter Park, FL 32792
GLOBAL PROPERTIES SALES/MGMT
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SOLD
JUN 26, 2026
$210,000
2 Beds
1.5 Baths
1,266 sqft
200 SAINT ANDREWS BOULEVARD #2901,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
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SOLD
JUN 26, 2026
$1,776,000
5 Beds
4.5 Baths
4,363 sqft
1177 KENWOOD AVENUE,
Winter Park, FL 32789
OPENDOOR BROKERAGE LLC
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SOLD
JUN 26, 2026
$1,000,000
3 Beds
2 Baths
2,111 sqft
520 FITZWALTER DRIVE,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
JUN 26, 2026
$284,000
2 Beds
1 Bath
1,317 sqft
1390 Clay St,
Winter Park, FL 32789
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SOLD
JUN 26, 2026
$421,500
3 Beds
2 Baths
1,678 sqft
2831 ANTIOCH WAY,
Orlando, FL 32807
EXIT REALTY PREMIER LEGACY
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SOLD
JUN 26, 2026
$2,080,000
4 Beds
3.5 Baths
3,472 sqft
2423 VIA SIENNA,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 26, 2026
$276,000
4 Beds
2 Baths
1,699 sqft
1011 Manchester Cir,
Winter Park, FL 32792
SOLD
JUN 26, 2026
$425,000
4 Beds
3 Baths
2,117 sqft
1923 LINDEN ROAD,
Winter Park, FL 32792
COLDWELL BANKER REALTY
SOLD
JUN 26, 2026
$207,000
3 Beds
2 Baths
1,332 sqft
5454 Bracken Ct,
Winter Park, FL 32792
EXP REALTY LLC
SOLD
JUN 26, 2026
$516,000
3 Beds
2.5 Baths
1,616 sqft
1781 INDIANA AVENUE #A,
Winter Park, FL 32789
CARLISLE REALTY, LLC
SOLD
JUN 25, 2026
$1,400,000
4 Beds
5.5 Baths
3,609 sqft
234 DETMAR DRIVE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 25, 2026
$892,500
3 Beds
3 Baths
1,864 sqft
1960 WINTER PARK ROAD,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 25, 2026
$2,755,000
5 Beds
4.5 Baths
4,091 sqft
670 WILLIAMS DRIVE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 25, 2026
$425,000
3 Beds
1 Bath
1,243 sqft
1416 BORDER DRIVE,
Winter Park, FL 32789
STELLAR NON-MEMBER OFFICE
SOLD
JUN 25, 2026
$379,000
3 Beds
2 Baths
1,363 sqft
1433 ASTER COURT,
Winter Park, FL 32792
RE/MAX TOWN & COUNTRY REALTY
SOLD
JUN 25, 2026
$452,000
3 Beds
2 Baths
1,715 sqft
2020 COCOS COURT,
Winter Park, FL 32792
SERHANT
SOLD
JUN 25, 2026
$135,000
1 Bed
1 Bath
678 sqft
144 Lewfield Cir,
Winter Park, FL 32792
SOLD
JUN 25, 2026
$892,500
1960 WINTER PARK ROAD LOT 16,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 24, 2026
$499,000
3 Beds
2 Baths
1,232 sqft
1871 BRYAN AVENUE,
Winter Park, FL 32789
CORCORAN PREMIER REALTY
SOLD
JUN 24, 2026
$615,000
3 Beds
2 Baths
1,283 sqft
1780 GOODRICH AVENUE,
Winter Park, FL 32789
SUMMERPARK HOMES REALTY LLC
SOLD
JUN 24, 2026
$400,000
2 Beds
2 Baths
1,018 sqft
721 DUNBAR STREET,
Winter Park, FL 32789
KELLER WILLIAMS REALTY AT THE PARKS
SOLD
JUN 24, 2026
$5,125,000
5 Beds
5.5 Baths
5,164 sqft
1221 RICHMOND ROAD,
Winter Park, FL 32789
LA ROSA REALTY HORIZONS LLC
SOLD
JUN 24, 2026
$310,000
2 Beds
1 Bath
860 sqft
1430 Michigan Ave,
Winter Park, FL 32789
SOLD
JUN 24, 2026
$450,000
4 Beds
2 Baths
2,024 sqft
1684 Bomi Cir,
Winter Park, FL 32792
SOLD
JUN 24, 2026
$277,000
3 Beds
2 Baths
1,050 sqft
5450 PEACO PLACE,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE 2 REALTY
SOLD
JUN 23, 2026
$450,000
3 Beds
3 Baths
1,970 sqft
7618 WAUNATTA COURT,
Winter Park, FL 32792
PHOENIX REALTY ADVISORS LLC
SOLD
JUN 23, 2026
$710,000
3 Beds
2 Baths
1,677 sqft
1108 FAIRWAY DRIVE,
Winter Park, FL 32792
CHARLES RUTENBERG REALTY ORLANDO
SOLD
JUN 23, 2026
$1,125,000
3 Beds
2.5 Baths
2,426 sqft
1651 WESTCHESTER AVENUE,
Winter Park, FL 32789
SERHANT
SOLD
JUN 22, 2026
$480,000
2 Beds
2 Baths
1,161 sqft
439 Berwick Dr,
Winter Park, FL 32792
SOLD
JUN 22, 2026
$217,000
2 Beds
1 Bath
854 sqft
2400 DOMINICA RUN,
Winter Park, FL 32792
FLORIDA HOME TEAM REALTY LLC
SOLD
JUN 22, 2026
$375,000
3 Beds
2.5 Baths
1,787 sqft
7485 ALOMA PINES COURT,
Winter Park, FL 32792
OLYMPUS EXECUTIVE REALTY INC
SOLD
JUN 22, 2026
$1,295,100
220 W READING WAY LOT 2,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
JUN 19, 2026
$595,000
3 Beds
2 Baths
1,610 sqft
1760 GREENWICH AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 19, 2026
$158,000
2 Beds
1 Bath
1,166 sqft
2531 Antilles Dr,
Winter Park, FL 32792
SOLD
JUN 18, 2026
$2,750,000
4 Beds
4.5 Baths
4,129 sqft
151 OAKWOOD WAY,
Winter Park, FL 32789
CORCORAN PREMIER REALTY
SOLD
JUN 18, 2026
$464,000
3 Beds
1 Bath
1,320 sqft
2242 Howard Dr,
Winter Park, FL 32789
SOLD
JUN 18, 2026
$1,201,000
3 Beds
2.5 Baths
2,608 sqft
1723 CHESTNUT AVENUE,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
SOLD
JUN 18, 2026
$450,000
3 Beds
2 Baths
1,482 sqft
7001 JACKMAN BOULEVARD,
Winter Park, FL 32792
COLDWELL BANKER REALTY
SOLD
JUN 18, 2026
$2,050,000
4 Beds
4.5 Baths
3,412 sqft
1636 ELIZABETHS WALK,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. 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