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Recently Sold Homes in Winter Park, FL

805 homes

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SOLD
JAN 16, 2026
$660,000
4 Beds
2.5 Baths
2,824 sqft
4019 Quenita Dr,
Winter Park, FL 32792
COMPASS FLORIDA LLC
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SOLD
JAN 16, 2026
$637,500
3 Beds
2.5 Baths
1,951 sqft
595 Huntington Ave #4,
Winter Park, FL 32789
COLDWELL BANKER RESIDENTIAL RE
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SOLD
JAN 16, 2026
$409,000
3 Beds
2 Baths
1,794 sqft
900 Carver St,
Winter Park, FL 32789
LEGACY REALTY & BROKERS LLC
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SOLD
JAN 16, 2026
$800,000
3 Beds
3.5 Baths
2,116 sqft
1251 Arlington Pl,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
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SOLD
JAN 16, 2026
$250,000
3 Beds
2 Baths
1,285 sqft
1605 Puritan Ave,
Winter Park, FL 32792
REALTY LYNK INC
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SOLD
JAN 15, 2026
$360,200
3 Beds
2 Baths
1,401 sqft
320 Granada Dr,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
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SOLD
JAN 15, 2026
$1,707,880
5 Beds
4 Baths
3,312 sqft
1417 Miller Ave,
Winter Park, FL 32789
CORCORAN PREMIER REALTY
SOLD
JAN 15, 2026
$420,000
4 Beds
2.5 Baths
1,477 sqft
1847 Azalea Ave,
Winter Park, FL 32789
COLDWELL BANKER REALTY
SOLD
JAN 15, 2026
$299,000
2 Beds
2 Baths
1,078 sqft
2804 Whispering Way,
Winter Park, FL 32792
TOP VALUE PROPERTIES LLC
SOLD
JAN 15, 2026
$470,000
5 Beds
3 Baths
1,546 sqft
3319 Ellwood Ct,
Winter Park, FL 32792
BALDWIN PARK REALTY LLC
SOLD
JAN 14, 2026
$912,500
4 Beds
3 Baths
2,838 sqft
210 Laurel Park Ct,
Winter Park, FL 32792
EXP REALTY LLC
SOLD
JAN 13, 2026
$425,000
3 Beds
2 Baths
1,562 sqft
2218 King Richards Ct,
Winter Park, FL 32792
EXP REALTY LLC
SOLD
JAN 12, 2026
$343,000
4 Beds
2 Baths
1,821 sqft
2829 Aloma Ave,
Winter Park, FL 32792
KELLER WILLIAMS CLASSIC
SOLD
JAN 12, 2026
$500,000
4 Beds
2 Baths
2,303 sqft
2758 Sandwell Dr,
Winter Park, FL 32792
CALL IT CLOSED INTL REALTY
SOLD
JAN 12, 2026
$1,900,000
4 Beds
3 Baths
2,918 sqft
2220 Via Tuscany,
Winter Park, FL 32789
SOLD
JAN 12, 2026
$1,865,375
5215 Howell Branch Rd,
Winter Park, FL 32792
RE/MAX TOWN & COUNTRY REALTY
SOLD
JAN 12, 2026
$750,000
3 Beds
2.5 Baths
1,957 sqft
1278 S Pennsylvania Ave #13,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
JAN 9, 2026
$405,000
3 Beds
2 Baths
1,516 sqft
3425 Ferndell Dr,
Winter Park, FL 32792
LOKATION
SOLD
JAN 8, 2026
$417,500
3 Beds
2 Baths
1,685 sqft
2148 Blossom Ln,
Winter Park, FL 32789
MP FLORIDA PROPERTY & REALTY INC
SOLD
JAN 8, 2026
$850,000
2 Beds
2 Baths
1,320 sqft
801 Audubon Ln,
Winter Park, FL 32789
SOTERA LIVING
SOLD
JAN 8, 2026
$750,000
4 Beds
2 Baths
2,111 sqft
1712 Golfside Dr,
Winter Park, FL 32792
ERA GRIZZARD REAL ESTATE
SOLD
JAN 8, 2026
$1,120,000
4 Beds
3 Baths
3,710 sqft
5236 Lake Howell Rd,
Winter Park, FL 32792
BHHS FLORIDA REALTY
SOLD
JAN 8, 2026
$425,000
4 Beds
2 Baths
2,195 sqft
5338 Tangerine Ave,
Winter Park, FL 32792
CENTURY 21 CARIOTI
SOLD
JAN 6, 2026
$622,500
2 Beds
2 Baths
1,637 sqft
1835 Jessica Ct,
Winter Park, FL 32789
EXP REALTY LLC
SOLD
JAN 6, 2026
$1,250,000
5 Beds
4 Baths
3,800 sqft
1440 Place Vendome,
Winter Park, FL 32789
SOLD
JAN 6, 2026
$425,000
3 Beds
2 Baths
1,640 sqft
5201 Ardmore Dr,
Winter Park, FL 32792
WRA BUSINESS & REAL ESTATE
SOLD
JAN 6, 2026
$180,000
2 Beds
2 Baths
1,018 sqft
2941 Antique Oaks Cir #79,
Winter Park, FL 32792
KELLER WILLIAMS CLASSIC
SOLD
JAN 5, 2026
$530,000
3 Beds
2 Baths
1,771 sqft
212 Blossom Ln,
Winter Park, FL 32789
BHHS FLORIDA REALTY
SOLD
JAN 5, 2026
$505,000
3 Beds
2 Baths
1,263 sqft
1651 N Park Ave,
Winter Park, FL 32789
COLDWELL BANKER RESIDENTIAL RE
SOLD
JAN 5, 2026
$190,000
2 Beds
2 Baths
1,120 sqft
626 Saint Johns Ct #S,
Winter Park, FL 32792
COLDWELL BANKER REALTY
SOLD
JAN 2, 2026
$4,800,000
5 Beds
5 Baths
6,699 sqft
641 Bonita Dr,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
JAN 2, 2026
$1,300,000
4 Beds
3 Baths
2,310 sqft
1400 S Pennsylvania Ave,
Winter Park, FL 32789
JACK KELLER INC
SOLD
JAN 2, 2026
$195,000
1 Bed
1 Bath
871 sqft
700 Melrose Ave #D21,
Winter Park, FL 32789
RE/MAX PRIME PROPERTIES
SOLD
JAN 2, 2026
$300,000
3 Beds
1 Bath
1,252 sqft
2565 Madeline Ave,
Winter Park, FL 32789
SOLD
JAN 2, 2026
$295,000
3 Beds
2.5 Baths
1,652 sqft
1509 Winter Green Blvd,
Winter Park, FL 32792
EXP REALTY LLC
SOLD
JAN 2, 2026
$570,000
2 Beds
2.5 Baths
1,718 sqft
640 Killarney Bay Ct #4,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
JAN 1, 2026
$315,000
2 Beds
2 Baths
1,221 sqft
615 Warrenton Rd,
Winter Park, FL 32792
RE/MAX DOWNTOWN
SOLD
JAN 1, 2026
$1,875,000
4 Beds
4.5 Baths
3,314 sqft
1752 Chestnut Ave,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
SOLD
JAN 1, 2026
$1,350,000
3 Beds
2.5 Baths
2,350 sqft
311 E Morse Blvd #8-1,
Winter Park, FL 32789
SOLD
DEC 31, 2025
$365,000
4 Beds
2 Baths
1,530 sqft
1083 Eastbrook Blvd,
Winter Park, FL 32792
ORANGE SLICE PROPERTIES

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