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Recently Sold Homes in Winter Park, FL

811 homes

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SOLD
MAR 2, 2026
$415,000
2 Beds
2 Baths
760 sqft
875 W Lyman Ave,
Winter Park, FL 32789
CHARLES RUTENBERG REALTY ORLANDO
SOLD
MAR 2, 2026
$615,000
3 Beds
2 Baths
1,433 sqft
2811 Eastern Pkwy,
Winter Park, FL 32789
RE/MAX TOWN & COUNTRY REALTY
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SOLD
MAR 2, 2026
$310,000
2 Beds
2 Baths
1,312 sqft
1886 Demetree Dr,
Winter Park, FL 32789
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SOLD
FEB 27, 2026
$180,000
2 Beds
2 Baths
987 sqft
200 Saint Andrews Blvd #2302,
Winter Park, FL 32792
COLDWELL BANKER REALTY
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SOLD
FEB 27, 2026
$1,100,000
2 Beds
2 Baths
1,267 sqft
100 S Interlachen Ave #415,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
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SOLD
FEB 27, 2026
$530,000
3 Beds
1.5 Baths
1,295 sqft
508 Darcey Dr,
Winter Park, FL 32792
OLDE TOWN BROKERS INC
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SOLD
FEB 27, 2026
$120,500
2 Beds
2 Baths
800 sqft
7326 Swallow Run #7326,
Winter Park, FL 32792
CREATIVE HOMES OF ORLANDO
SOLD
FEB 27, 2026
$5,400,000
5 Beds
7 Baths
7,916 sqft
1400 Alabama Dr,
Winter Park, FL 32789
THE AGENCY FL
SOLD
FEB 27, 2026
$379,990
3 Beds
2 Baths
1,424 sqft
1378 Chilean Ln,
Winter Park, FL 32792
FUTURE HOME REALTY INC
SOLD
FEB 26, 2026
$325,100
4 Beds
2 Baths
1,979 sqft
3949 Cool Water Ct,
Winter Park, FL 32792
SOLD
FEB 26, 2026
$1,700,000
4 Beds
3 Baths
2,749 sqft
1571 Lasbury Ave,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
SOLD
FEB 26, 2026
$755,000
4 Beds
2 Baths
2,015 sqft
1317 Medinah Ct,
Winter Park, FL 32792
SAND DOLLAR REALTY GROUP INC
SOLD
FEB 26, 2026
$340,000
3 Beds
3.5 Baths
1,872 sqft
7580 Aloma Pines Ct,
Winter Park, FL 32792
USCO CAPITAL GROUP
SOLD
FEB 26, 2026
$700,000
2002 Karolina Ave #8,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
FEB 25, 2026
$502,000
4 Beds
3 Baths
1,835 sqft
326 Fitzhugh Rd,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
FEB 25, 2026
$1,115,000
4 Beds
4 Baths
2,540 sqft
1673 Mayfield Ave,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
FEB 25, 2026
$630,000
3 Beds
2 Baths
1,252 sqft
2805 Northwood Blvd,
Winter Park, FL 32789
LIVE OAK EQUITIES
SOLD
FEB 25, 2026
$714,000
4 Beds
2.5 Baths
2,928 sqft
1449 Pelican Bay Trl,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
FEB 25, 2026
$330,000
3 Beds
2 Baths
1,446 sqft
1573 Lawndale Cir,
Winter Park, FL 32792
KELLER WILLIAMS WINTER PARK
SOLD
FEB 24, 2026
$234,000
2 Beds
1 Bath
710 sqft
151 N Orlando Ave #204,
Winter Park, FL 32789
MAINFRAME REAL ESTATE
SOLD
FEB 24, 2026
$955,000
4 Beds
3.5 Baths
2,824 sqft
512 Clarendon Ave,
Winter Park, FL 32789
COMPASS FLORIDA LLC
SOLD
FEB 24, 2026
$830,000
4 Beds
2 Baths
2,020 sqft
1717 Golfside Dr,
Winter Park, FL 32792
FANNIE HILLMAN & ASSOCIATES
SOLD
FEB 24, 2026
$13,000,000
6 Beds
7.5 Baths
12,190 sqft
2203 Via Tuscany,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
FEB 24, 2026
$1,280,000
4 Beds
4 Baths
3,116 sqft
1429 Chapman Cir,
Winter Park, FL 32789
CORCORAN PREMIER REALTY
SOLD
FEB 24, 2026
$3,800,000
3 Beds
4 Baths
4,237 sqft
637 N Park Ave,
Winter Park, FL 32789
COLDWELL BANKER REALTY
SOLD
FEB 24, 2026
$192,000
2 Beds
2 Baths
1,120 sqft
623 Saint Johns Ct #623,
Winter Park, FL 32792
CENTURY 21 CARIOTI
SOLD
FEB 24, 2026
$268,000
2 Beds
2 Baths
893 sqft
609 Gallery Dr #B204,
Winter Park, FL 32792
A2Z REALTY GROUP
SOLD
FEB 23, 2026
$390,000
3 Beds
2 Baths
1,401 sqft
1670 Clematis Ln,
Winter Park, FL 32792
LPT REALTY, LLC
SOLD
FEB 23, 2026
$125,000
3 Beds
2 Baths
1,149 sqft
1695 Lee Rd #B216,
Winter Park, FL 32789
EXP REALTY LLC
SOLD
FEB 20, 2026
$530,000
3 Beds
2 Baths
1,875 sqft
151 N Orlando Ave #212,
Winter Park, FL 32789
THE AGENCY FL
SOLD
FEB 20, 2026
$300,000
2 Beds
1 Bath
754 sqft
600 W Webster Ave,
Winter Park, FL 32789
REALTY ONE GROUP MVP
SOLD
FEB 20, 2026
$1,900,000
4 Beds
4.5 Baths
3,515 sqft
319 Santiago Dr,
Winter Park, FL 32789
ANNE ROGERS REALTY GROUP INC
SOLD
FEB 20, 2026
$198,000
2 Beds
2.5 Baths
1,031 sqft
7457 Belle River Ct #12,
Winter Park, FL 32792
LIFESTYLE INTERNATIONAL REALTY
SOLD
FEB 20, 2026
$690,000
3 Beds
2 Baths
1,512 sqft
2904 Parkland Dr,
Winter Park, FL 32789
STELLAR NON-MEMBER OFFICE
SOLD
FEB 20, 2026
$450,000
3 Beds
2 Baths
1,671 sqft
1932 Houndslake Dr,
Winter Park, FL 32792
LA ROSA REALTY LLC
SOLD
FEB 20, 2026
$109,900
Studio
890 sqft
3651 N Goldenrod Rd,
Winter Park, FL 32792
SOLD
FEB 20, 2026
$325,000
3 Beds
2.5 Baths
1,408 sqft
3136 Crown Jewel Ct,
Winter Park, FL 32792
REALTY RESOURCE OF CENTRAL FL.
SOLD
FEB 19, 2026
$414,000
3 Beds
2 Baths
1,456 sqft
740 Baffie Ave,
Winter Park, FL 32789
CREEGAN GROUP
SOLD
FEB 19, 2026
$1,500,000
2 Beds
2 Baths
1,609 sqft
315 New England Ave #7,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
SOLD
FEB 19, 2026
$60,000
2 Beds
2 Baths
1,088 sqft
3028 George Mason Ave #7,
Winter Park, FL 32792
FLORIDA REALTY INVESTMENTS

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