Recently Sold Homes in 32789

363 homes

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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
$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
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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
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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
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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
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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
$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
$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
$560,000
3 Beds
2 Baths
1,618 sqft
218 Orange Terrace Dr,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
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 1, 2026
$342,500
2 Beds
2 Baths
1,074 sqft
700 Melrose Ave #J1,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
MAY 1, 2026
$1,650,000
4 Beds
3 Baths
3,142 sqft
1016 Howell Branch Rd,
Winter Park, FL 32789
PLAID PROPERTIES, LLC
SOLD
APR 30, 2026
$795,000
3 Beds
2 Baths
1,893 sqft
1680 Palmer Ave,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 30, 2026
$550,000
2 Beds
2 Baths
986 sqft
535 N Interlachen Ave #203,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 30, 2026
$800,000
3 Beds
2 Baths
1,930 sqft
737 N Capen Ave,
Winter Park, FL 32789
LPT REALTY, LLC
SOLD
APR 30, 2026
$4,500,000
6 Beds
5.5 Baths
5,759 sqft
887 Georgia Ave,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 30, 2026
$800,000
3 Beds
2 Baths
1,800 sqft
422 Balmoral Rd,
Winter Park, FL 32789
CENTRAL FLORIDA REAL ESTATE CE
SOLD
APR 30, 2026
$1,390,000
4 Beds
4.5 Baths
3,253 sqft
525 Lakeview Ave,
Winter Park, FL 32789
COLDWELL BANKER REALTY
SOLD
APR 30, 2026
$2,050,000
1205 Mayfield Ave #9,
Winter Park, FL 32789
RE/MAX 200 REALTY
SOLD
APR 27, 2026
$1,425,000
4 Beds
3.5 Baths
2,544 sqft
823 Granville Dr,
Winter Park, FL 32789
FLORIDA ONE REAL ESTATE LLC
SOLD
APR 24, 2026
$105,000
2 Beds
1 Bath
881 sqft
1695 Lee Rd #C214,
Winter Park, FL 32789
PROFESSIONAL REAL ESTATE TEAM
SOLD
APR 24, 2026
$300,000
1 Bed
1 Bath
570 sqft
311 E Morse Blvd #6-3,
Winter Park, FL 32789
FLORIDA ONE REAL ESTATE LLC
SOLD
APR 23, 2026
$145,000
1 Bed
1 Bath
645 sqft
2500 Lee Rd #243,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
SOLD
APR 22, 2026
$1,600,000
4 Beds
2.5 Baths
3,263 sqft
446 Alberta Dr,
Winter Park, FL 32789
CHARLES RUTENBERG REALTY ORLANDO
SOLD
APR 17, 2026
$372,400
4 Beds
1.5 Baths
1,248 sqft
770 Carver St,
Winter Park, FL 32789
LEGENDS REALTY
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
$1,100,000
2 Beds
2 Baths
1,402 sqft
1602 Alabama Dr #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 Ave #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 Cir,
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
$110,000
2 Beds
1 Bath
881 sqft
1695 Lee Road E211,
Winter Park, FL 32789
KELLER WILLIAMS REALTY SMART 1
SOLD
APR 13, 2026
$610,000
1860 Staunton Ave,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
APR 13, 2026
$3,100,001
5 Beds
4.5 Baths
4,686 sqft
611 Williams Dr,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES

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Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511