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Recently Sold 2 Bedroom Homes in Winter Park, FL

822 homes

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SOLD
JUN 29, 2026
$660,000
4 Beds
3 Baths
1,918 sqft
927 FAIRWAY DRIVE,
Winter Park, FL 32792
FLAT FEE MLS REALTY
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SOLD
JUN 29, 2026
$640,000
4 Beds
1 Bath
1,604 sqft
1618 Indiana Ave 1618 Indiana Ave,
Winter Park, FL 32789
NATIONAL REAL ESTATE
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SOLD
JUN 29, 2026
$3,150,000
4 Beds
5.5 Baths
3,788 sqft
1910 GLENCOE ROAD,
Winter Park, FL 32789
ONE LUXURY INTERNATIONAL LLC
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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
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SOLD
JUN 26, 2026
$276,000
4 Beds
2 Baths
1,699 sqft
1011 Manchester Cir,
Winter Park, FL 32792
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SOLD
JUN 26, 2026
$425,000
4 Beds
3 Baths
2,117 sqft
1923 LINDEN ROAD,
Winter Park, FL 32792
COLDWELL BANKER REALTY
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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 24, 2026
$450,000
4 Beds
2 Baths
2,024 sqft
1684 Bomi Cir,
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
$2,050,000
4 Beds
4.5 Baths
3,412 sqft
1636 ELIZABETHS WALK,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
JUN 17, 2026
$3,755,000
4 Beds
4.5 Baths
4,353 sqft
1117 KENWOOD AVENUE,
Winter Park, FL 32789
ROYALTY R E BOUTIQUE INC
SOLD
JUN 17, 2026
$489,000
4 Beds
2 Baths
1,843 sqft
5236 ALBERT DRIVE,
Winter Park, FL 32792
COLDWELL BANKER REALTY
SOLD
JUN 16, 2026
$640,000
4 Beds
2 Baths
2,369 sqft
3966 LAKE MIRA DRIVE,
Orlando, FL 32817
CHARLES RUTENBERG REALTY ORLANDO
SOLD
JUN 16, 2026
$2,200,000
4 Beds
4 Baths
5,051 sqft
2550 VENETIAN WAY,
Winter Park, FL 32789
PALM PROPERTIES OF CF, INC.
SOLD
JUN 16, 2026
$220,000
4 Beds
2 Baths
1,372 sqft
3382 Bougainvillea Dr,
Winter Park, FL 32792
SOLD
JUN 16, 2026
$470,000
4 Beds
2 Baths
1,753 sqft
7120 BROOKSIDE TRAIL,
Winter Park, FL 32792
KELLY PRICE & COMPANY LLC
SOLD
JUN 16, 2026
$1,100,000
4 Beds
3.5 Baths
3,153 sqft
2922 REEF KNOT PLACE,
Winter Park, FL 32792
CHARLES RUTENBERG REALTY ORLANDO
SOLD
JUN 12, 2026
$715,000
4 Beds
2 Baths
1,599 sqft
688 BRECHIN DRIVE,
Winter Park, FL 32792
PREMIER SOTHEBY'S INTL. REALTY
SOLD
JUN 12, 2026
$435,000
4 Beds
2.5 Baths
1,946 sqft
5210 OHIO STREET,
Winter Park, FL 32792
REAL BROKER, LLC
SOLD
JUN 11, 2026
$887,500
4 Beds
3 Baths
2,086 sqft
627 DUNBLANE DRIVE,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
JUN 10, 2026
$715,000
4 Beds
3 Baths
2,768 sqft
8243 RIVIERA SHORE COURT,
Orlando, FL 32817
KELLER WILLIAMS HERITAGE REALTY
SOLD
JUN 9, 2026
$401,000
4 Beds
2 Baths
1,988 sqft
3330 COLEUS COURT,
Winter Park, FL 32792
MAINSTAY BROKERAGE LLC
SOLD
JUN 5, 2026
$1,875,000
4 Beds
4.5 Baths
3,657 sqft
543 E LAKE SUE AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JUN 5, 2026
$470,000
4 Beds
2.5 Baths
1,906 sqft
3167 ASH PARK LOOP,
Winter Park, FL 32792
REAL BROKER, LLC
SOLD
JUN 5, 2026
$985,000
4 Beds
3 Baths
3,057 sqft
1453 VIA SANGRO PLACE,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE REALTY
SOLD
JUN 4, 2026
$406,000
4 Beds
2 Baths
1,048 sqft
1812 KILLARNEY DRIVE,
Winter Park, FL 32789
HANSON REAL ESTATE GROUP, INC.
SOLD
JUN 4, 2026
$445,000
4 Beds
2 Baths
1,808 sqft
1832 E CHERYL DRIVE,
Winter Park, FL 32792
SELECTIVE REALTY GROUP LLC
SOLD
JUN 4, 2026
$370,000
4 Beds
2 Baths
2,050 sqft
1409 Aster Ct,
Winter Park, FL 32792
SOLD
JUN 3, 2026
$1,900,000
4 Beds
2.5 Baths
2,841 sqft
1760 ALABAMA DRIVE,
Winter Park, FL 32789
DAILLAND REAL ESTATE
SOLD
JUN 1, 2026
$4,250,000
4 Beds
4 Baths
3,181 sqft
1336 COLLEGE POINT,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
MAY 29, 2026
$4,500,000
4 Beds
4.5 Baths
3,922 sqft
1521 HARRIS CIRCLE,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
MAY 29, 2026
$600,000
4 Beds
2 Baths
1,750 sqft
2330 COLDSTREAM DRIVE,
Winter Park, FL 32792
DTB FLORIDA REALTY, INC.
SOLD
MAY 29, 2026
$4,300,000
4 Beds
6.5 Baths
6,242 sqft
1760 VIA VENETIA,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
MAY 28, 2026
$482,000
4 Beds
3 Baths
1,378 sqft
958 HANOVER AVENUE,
Winter Park, FL 32789
AGILE GROUP REALTY
SOLD
MAY 28, 2026
$2,032,850
4 Beds
3.5 Baths
3,195 sqft
872 GRANVILLE DRIVE,
Winter Park, FL 32789
CORCORAN PREMIER REALTY
SOLD
MAY 26, 2026
$400,000
4 Beds
3 Baths
2,295 sqft
4269 Steed Ter,
Winter Park, FL 32792
SOLD
MAY 26, 2026
$581,000
4 Beds
2.5 Baths
2,157 sqft
7917 PLEASANT PINE CIRCLE,
Winter Park, FL 32792
LORI GILMORE REAL ESTATE LLC
SOLD
MAY 22, 2026
$775,000
4 Beds
2 Baths
2,112 sqft
521 FAIRFAX AVENUE,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
MAY 22, 2026
$841,500
4 Beds
5.5 Baths
2,479 sqft
2119 HOWARD DRIVE,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
SOLD
MAY 22, 2026
$455,000
4 Beds
2 Baths
1,659 sqft
1240 Gladiolas Dr,
Winter Park, FL 32792

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