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Recently Sold Homes in Winter Park, FL

902 homes

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SOLD
MAY 21, 2026
$2,185,000
5 Beds
4.5 Baths
3,334 sqft
2722 EASTERN PARKWAY,
Winter Park, FL 32789
ONE LUXURY INTERNATIONAL LLC
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SOLD
MAY 21, 2026
$500,000
4 Beds
2 Baths
1,774 sqft
1905 BONANZA CT,
Winter Park, FL 32792
REAL LIVING R E SOLUTIONS
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SOLD
MAY 21, 2026
$1,000,000
3 Beds
3.5 Baths
3,174 sqft
101 S NEW YORK AVENUE #302,
Winter Park, FL 32789
COLDWELL BANKER REALTY
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SOLD
MAY 21, 2026
$73,500
1 Bed
1 Bath
809 sqft
3053 GEORGE MASON AVENUE #8A,
Winter Park, FL 32792
COLDWELL BANKER REALTY
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SOLD
MAY 21, 2026
$1,969,000
2 Beds
2 Baths
1,900 sqft
311 E MORSE BOULEVARD #2 - 5,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
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SOLD
MAY 20, 2026
$765,000
4 Beds
2.5 Baths
2,375 sqft
2681 FITZHUGH ROAD,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
MAY 20, 2026
$450,000
3 Beds
2 Baths
1,487 sqft
2346 Coldstream Dr,
Winter Park, FL 32792
SOLD
MAY 20, 2026
$3,278,530
4 Beds
4.5 Baths
3,897 sqft
700 PINETREE ROAD,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 20, 2026
$265,100
3 Beds
2 Baths
1,509 sqft
7348 Grand Ave,
Winter Park, FL 32792
SOLD
MAY 19, 2026
$1,500,000
2 Beds
2 Baths
2,281 sqft
246 PALMER AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 19, 2026
$1,425,000
4 Beds
3 Baths
2,306 sqft
850 JUANITA RAEL,
Winter Park, FL 32789
PHIL KEAN REAL ESTATE LLC
SOLD
MAY 19, 2026
$735,000
4 Beds
3.5 Baths
2,998 sqft
675 Overspin Dr,
Winter Park, FL 32789
SOLD
MAY 19, 2026
$1,500,000
246 PALMER AVENUE LOT 2,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 18, 2026
$180,000
1 Bed
1 Bath
727 sqft
200 SAINT ANDREWS BOULEVARD #705,
Winter Park, FL 32792
WINTER PARK REAL ESTATE CO LLC
SOLD
MAY 18, 2026
$830,000
3 Beds
1 Bath
1,318 sqft
1741 OAKHURST AVENUE,
Winter Park, FL 32789
STELLAR NON-MEMBER OFFICE
SOLD
MAY 18, 2026
$3,978,550
4 Beds
4.5 Baths
4,665 sqft
2020 VIA TUSCANY,
Winter Park, FL 32789
VISTA CAY REALTY COMPANY
SOLD
MAY 18, 2026
$410,000
3 Beds
2 Baths
1,485 sqft
7761 FOX KNOLL PLACE,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE 2 REALTY
SOLD
MAY 15, 2026
$1,300,000
3 Beds
3.5 Baths
3,215 sqft
1661 WOODLAND AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 15, 2026
$3,000,000
5 Beds
5.5 Baths
4,296 sqft
473 FLETCHER PLACE,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
MAY 15, 2026
$4,720,000
5 Beds
5.5 Baths
4,738 sqft
1302 RAINTREE PLACE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 15, 2026
$7,164,000
5 Beds
6.5 Baths
5,006 sqft
1821 PINETREE ROAD,
Winter Park, FL 32789
ONE LUXURY INTERNATIONAL LLC
SOLD
MAY 15, 2026
$600,000
4 Beds
3 Baths
2,704 sqft
3110 HEARTLEAF PLACE,
Winter Park, FL 32792
FUSILIER MANAGEMENT GROUP
SOLD
MAY 15, 2026
$469,900
3 Beds
2 Baths
1,624 sqft
1280 GLADIOLAS DR,
Winter Park, FL 32792
FLORIDA PRESTIGIOUS HOMES INC
SOLD
MAY 15, 2026
$435,000
3 Beds
2 Baths
1,576 sqft
7445 BETTY STREET,
Winter Park, FL 32792
LISTY, LLC
SOLD
MAY 15, 2026
$354,900
3 Beds
2 Baths
1,642 sqft
5330 TANGERINE AVENUE,
Winter Park, FL 32792
MILLER GRANT AND COMPANY
SOLD
MAY 15, 2026
$340,000
3 Beds
2 Baths
1,575 sqft
7529 VILLAGE GREEN DRIVE,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE REALTY
SOLD
MAY 15, 2026
$1,000,000
6 Beds
6 Baths
4,056 sqft
1903 S Lakemont Ave,
Winter Park, FL 32792
Platinum Properties Int'l Inc.
SOLD
MAY 14, 2026
$475,000
3 Beds
2 Baths
1,119 sqft
665 LYMAN AVENUE,
Winter Park, FL 32789
CENTRAL FLORIDA PRIME REAL ESTATE LLC
SOLD
MAY 14, 2026
$700,000
5 Beds
4 Baths
2,765 sqft
1106 GOLFSIDE DRIVE,
Winter Park, FL 32792
STELLAR NON-MEMBER OFFICE
SOLD
MAY 14, 2026
$285,000
3 Beds
1.5 Baths
1,332 sqft
7796 FERNBROOK WAY,
Winter Park, FL 32792
PREMIER SOTHEBY'S INTL. REALTY
SOLD
MAY 14, 2026
$1,655,000
4 Beds
3.5 Baths
3,031 sqft
629 COUNTRY CLUB DRIVE,
Winter Park, FL 32789
CLASSIC HOMES
SOLD
MAY 13, 2026
$261,000
2 Beds
2 Baths
1,026 sqft
1500 GAY ROAD #8D,
Winter Park, FL 32789
SOLID OAK REAL ESTATE LLC
SOLD
MAY 13, 2026
$760,000
3 Beds
2 Baths
2,325 sqft
2919 BOWER ROAD,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
MAY 13, 2026
$365,000
2 Beds
1 Bath
936 sqft
765 BAFFIE AVENUE,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
SOLD
MAY 13, 2026
$450,000
2 Beds
2 Baths
1,609 sqft
518 SHOREVIEW AVENUE,
Winter Park, FL 32789
UNITED REAL ESTATE PREFERRED
SOLD
MAY 12, 2026
$440,000
5 Beds
3 Baths
1,945 sqft
3642 PERIWINKLE DRIVE,
Winter Park, FL 32792
HONEST REAL ESTATE COMPANY
SOLD
MAY 12, 2026
$2,570,000
3 Beds
3 Baths
2,667 sqft
135 W SWOOPE AVENUE,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
MAY 11, 2026
$530,000
3 Beds
2 Baths
1,275 sqft
1921 KIMBRACE PLACE,
Winter Park, FL 32792
COMPASS FLORIDA LLC
SOLD
MAY 11, 2026
$2,000,000
3 Beds
4.5 Baths
5,138 sqft
2820 BEAR ISLAND POINTE,
Winter Park, FL 32792
KELLY PRICE & COMPANY LLC
SOLD
MAY 11, 2026
$1,635,000
4 Beds
3.5 Baths
3,470 sqft
1841 HARLAND PARK DRIVE,
Winter Park, FL 32789
SELECTIVE REALTY GROUP LLC

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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

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.