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Recently Sold 2 Bedroom Homes in Winter Park, FL

820 homes

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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
SOLD
MAY 20, 2026
$450,000
3 Beds
2 Baths
1,487 sqft
2346 Coldstream Dr,
Winter Park, FL 32792
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SOLD
MAY 20, 2026
$265,100
3 Beds
2 Baths
1,509 sqft
7348 Grand Ave,
Winter Park, FL 32792
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SOLD
MAY 18, 2026
$830,000
3 Beds
1 Bath
1,318 sqft
1741 OAKHURST AVENUE,
Winter Park, FL 32789
STELLAR NON-MEMBER OFFICE
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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
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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
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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 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
$285,000
3 Beds
1.5 Baths
1,332 sqft
7796 FERNBROOK WAY,
Winter Park, FL 32792
PREMIER SOTHEBY'S INTL. REALTY
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 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 8, 2026
$560,000
3 Beds
2 Baths
1,618 sqft
218 ORANGE TERRACE DRIVE,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
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 7, 2026
$776,533
3 Beds
2 Baths
1,566 sqft
781 NORTHWOOD CIRCLE,
Winter Park, FL 32789
COLDWELL BANKER REALTY
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
SOLD
MAY 5, 2026
$720,000
3 Beds
2 Baths
1,575 sqft
643 DUNBLANE DRIVE,
Winter Park, FL 32792
ZEN LIVING HOMES LLC
SOLD
MAY 4, 2026
$150,000
3 Beds
2 Baths
1,120 sqft
2717 Eastham Rd,
Winter Park, FL 32792
SOLD
MAY 4, 2026
$470,000
3 Beds
2.5 Baths
2,312 sqft
1537 BANTAM WAY,
Winter Park, FL 32792
LIVE MVRK LLC
SOLD
MAY 1, 2026
$432,500
3 Beds
2 Baths
1,611 sqft
7716 WICKLOW CIRCLE,
Orlando, FL 32817
CHARLES RUTENBERG REALTY ORLANDO
SOLD
APR 30, 2026
$425,000
3 Beds
2 Baths
1,355 sqft
1909 EDWIN BOULEVARD,
Winter Park, FL 32792
CHARLES RUTENBERG REALTY ORLANDO
SOLD
APR 30, 2026
$795,000
3 Beds
2 Baths
1,893 sqft
1680 PALMER AVENUE,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 30, 2026
$800,000
3 Beds
2 Baths
1,930 sqft
737 N CAPEN AVENUE,
Winter Park, FL 32789
LPT REALTY, LLC
SOLD
APR 29, 2026
$421,000
3 Beds
2 Baths
1,400 sqft
633 LANDER ROAD,
Winter Park, FL 32792
KELLER WILLIAMS ADVANTAGE 2 REALTY
SOLD
APR 29, 2026
$360,000
3 Beds
2 Baths
1,310 sqft
5647 GARDEN GROVE,
Winter Park, FL 32792
WATSON REALTY CORP
SOLD
APR 27, 2026
$435,800
3 Beds
2 Baths
1,560 sqft
5418 ARDMORE DRIVE,
Winter Park, FL 32792
WEMERT GROUP REALTY LLC
SOLD
APR 24, 2026
$865,000
3 Beds
2.5 Baths
2,114 sqft
628 DUNBLANE DRIVE,
Winter Park, FL 32792
FANNIE HILLMAN & ASSOCIATES
SOLD
APR 24, 2026
$409,000
3 Beds
2 Baths
1,670 sqft
4048 Waterview Loop,
Winter Park, FL 32792
SOLD
APR 23, 2026
$490,000
3 Beds
2 Baths
1,745 sqft
2126 N HAMPTON CIRCLE,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
APR 21, 2026
$385,000
3 Beds
2.5 Baths
1,755 sqft
2232 SHADOWLAND LOOP,
Winter Park, FL 32792
U S GLORY 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 14, 2026
$430,000
3 Beds
2.5 Baths
1,756 sqft
1375 MERRYDALE WAY,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
APR 13, 2026
$365,000
3 Beds
2 Baths
1,552 sqft
5097 Lake Howell Rd,
Winter Park, FL 32792
SOLD
APR 13, 2026
$376,000
3 Beds
2 Baths
1,424 sqft
3324 BALSAM DRIVE,
Winter Park, FL 32792
KELLER WILLIAMS REALTY AT THE PARKS
SOLD
APR 10, 2026
$250,000
3 Beds
1.5 Baths
1,232 sqft
1823 MAYWOOD ROAD,
Winter Park, FL 32792
RE/MAX 200 REALTY

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