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Recently Sold Homes in Winter Park, FL

811 homes

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SOLD
MAY 18, 2026
$830,000
3 Beds
1 Bath
1,318 sqft
1741 Oakhurst Ave,
Winter Park, FL 32789
STELLAR NON-MEMBER OFFICE
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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
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SOLD
MAY 18, 2026
$410,000
3 Beds
2 Baths
1,485 sqft
7761 Fox Knoll Pl,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE 2 REALTY
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SOLD
MAY 15, 2026
$1,300,000
3 Beds
3.5 Baths
3,215 sqft
1661 Woodland Ave,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
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SOLD
MAY 15, 2026
$3,000,000
5 Beds
5.5 Baths
4,296 sqft
473 Fletcher Pl,
Winter Park, FL 32789
COMPASS FLORIDA LLC
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SOLD
MAY 15, 2026
$4,720,000
5 Beds
5.5 Baths
4,738 sqft
1302 Raintree Pl,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
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SOLD
MAY 15, 2026
$7,164,000
5 Beds
6.5 Baths
5,006 sqft
1821 Pinetree Rd,
Winter Park, FL 32789
ONE LUXURY INTERNATIONAL LLC
SOLD
MAY 15, 2026
$600,000
4 Beds
3 Baths
2,704 sqft
3110 Heartleaf Pl,
Winter Park, FL 32792
FUSILIER MANAGEMENT GROUP
SOLD
MAY 15, 2026
$435,000
3 Beds
2 Baths
1,576 sqft
7445 Betty St,
Winter Park, FL 32792
LISTY, LLC
SOLD
MAY 15, 2026
$354,900
3 Beds
2 Baths
1,642 sqft
5330 Tangerine Ave,
Winter Park, FL 32792
MILLER GRANT AND COMPANY
SOLD
MAY 15, 2026
$340,000
3 Beds
2 Baths
1,575 sqft
7529 Village Green Dr,
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 W Lyman Ave,
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 Dr,
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 Dr,
Winter Park, FL 32789
CLASSIC HOMES
SOLD
MAY 13, 2026
$261,000
2 Beds
2 Baths
1,026 sqft
1500 Gay Rd #8D,
Winter Park, FL 32789
SOLID OAK REAL ESTATE LLC
SOLD
MAY 13, 2026
$175,000
2 Beds
1.5 Baths
1,219 sqft
200 Saint Andrews Blvd #3103,
Winter Park, FL 32792
LPT REALTY, LLC
SOLD
MAY 13, 2026
$760,000
3 Beds
2 Baths
2,325 sqft
2919 Bower Rd,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
MAY 13, 2026
$365,000
2 Beds
1 Bath
936 sqft
765 Baffie Ave,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
SOLD
MAY 13, 2026
$450,000
2 Beds
2 Baths
1,609 sqft
518 Shoreview Ave,
Winter Park, FL 32789
UNITED REAL ESTATE PREFERRED
SOLD
MAY 12, 2026
$440,000
5 Beds
3 Baths
1,945 sqft
3642 Periwinkle Dr,
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 Ave,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
MAY 11, 2026
$530,000
3 Beds
2 Baths
1,275 sqft
1921 Kimbrace Pl,
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 Point,
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 Dr,
Winter Park, FL 32789
SELECTIVE REALTY GROUP LLC
SOLD
MAY 8, 2026
$1,675,000
5 Beds
4.5 Baths
3,851 sqft
1560 Woodland Ave,
Winter Park, FL 32789
CREEGAN GROUP
SOLD
MAY 8, 2026
$400,000
1 Bed
2 Baths
1,149 sqft
300 Carolina Ave #207,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 8, 2026
$1,325,000
4 Beds
3.5 Baths
3,651 sqft
409 Balmoral Rd,
Winter Park, FL 32789
SOLD
MAY 8, 2026
$1,700,000
4 Beds
2.5 Baths
2,754 sqft
633 Balmoral Rd,
Winter Park, FL 32789
SOLD
MAY 8, 2026
$795,000
4 Beds
3 Baths
1,950 sqft
639 Friar Rd,
Winter Park, FL 32792
FLORIDA REALTY INVESTMENTS
SOLD
MAY 8, 2026
$560,000
3 Beds
2 Baths
1,618 sqft
218 Orange Terrace Dr,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
SOLD
MAY 8, 2026
$115,000
2 Beds
2 Baths
1,072 sqft
1000 S Semoran Blvd #512,
Winter Park, FL 32792
REALSOURCE PROPERTY MANGNT LLC
SOLD
MAY 8, 2026
$445,000
3 Beds
2.5 Baths
2,312 sqft
2420 Firstlight Way,
Winter Park, FL 32792
ATRIUM REALTY, LLC
SOLD
MAY 8, 2026
$650,000
4 Beds
2.5 Baths
1,770 sqft
1098 Wildmeadow Run,
Winter Park, FL 32792
PREMIER SOTHEBY'S INTL. REALTY
SOLD
MAY 7, 2026
$776,533
3 Beds
2 Baths
1,566 sqft
781 Northwood Cir,
Winter Park, FL 32789
COLDWELL BANKER REALTY
SOLD
MAY 7, 2026
$225,000
2 Beds
2.5 Baths
959 sqft
#8,
Winter Park, FL 32789
DERENTHAL REALTY
SOLD
MAY 7, 2026
$1,700,000
633 Balmoral Rd #5,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
MAY 6, 2026
$439,000
4 Beds
2 Baths
1,771 sqft
837 Appalachee Ave,
Winter Park, FL 32792
KELLY PRICE & COMPANY LLC
SOLD
MAY 6, 2026
$415,000
3 Beds
2 Baths
1,518 sqft
3127 Ash Park Loop,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK

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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.