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433 listings in Winter Park
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Winter Park
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Listings
$695,000
715 S RANGER BLVD
WINTER PARK, 32792
4 bd·3 ba·2,312 sqft
89 days on market
Pool
Listed by DAHLIA REALTY GROUP
$500,000
2054 EASTBROOK BLVD
WINTER PARK, 32792
4 bd·3 ba·2,031 sqft
85 days on market
Pool
Listed by Melissa Stalzer, LPT REALTY, LLC
$649,900
860 N DENNING DR
WINTER PARK, 32789
3 bd·2.5 ba·1,411 sqft
135 days on market
Listed by LaDarrius Sanders, OUTLET REALTY
$836,000
338 BLUE HERON DR
WINTER PARK, 32789
3 bd·3 ba·2,017 sqft
126 days on market
Pool
Listed by STOCKWORTH REALTY GROUP
$6,000,000
1571 WOODLAND AVE
WINTER PARK, 32789
5 bd·7 ba·7,397 sqft
21 days on market
Pool
Listed by Vonda Fields, CHARLES RUTENBERG REALTY ORLANDO
$998,000
1404 BORDER DR
WINTER PARK, 32789
4 bd·4 ba·2,469 sqft
134 days on market
Listed by Brian Hyser, THE AGENCY FL
$2,375,000
946 ENCLAVE PL
WINTER PARK, 32792
5 bd·4.5 ba·3,989 sqft
131 days on market
PoolNew construction
Listed by Matthew Burks, CORCORAN PREMIER REALTY
$2,195,000
942 ENCLAVE PL
WINTER PARK, 32792
5 bd·5 ba·3,831 sqft
44 days on market
PoolNew construction
Listed by Matthew Burks, CORCORAN PREMIER REALTY
$2,125,000
950 ENCLAVE PL
WINTER PARK, 32792
5 bd·4.5 ba·3,797 sqft
44 days on market
PoolNew construction
Listed by Laura Earl, CORCORAN PREMIER REALTY
$1,600,000
723 SYMONDS AVE
WINTER PARK, 32789
4 bd·4 ba·3,065 sqft
140 days on market
Listed by Nick McKee, KELLER WILLIAMS WINTER PARK
$1,498,000
1841 LAKE SPIER DRIVE
WINTER PARK, 32789
3 bd·4 ba·2,467 sqft
138 days on market
Waterfront
Listed by Nicole Seybold, FANNIE HILLMAN & ASSOCIATES
$1,049,900
1448 LAKE FLORENCE WAY
WINTER PARK, 32792
5 bd·4.5 ba·3,652 sqft
139 days on market
Pool
Listed by Abby Nelson, RE/MAX 200 REALTY
$623,000
2418 EUSTON RD
WINTER PARK, 32789
3 bd·2.5 ba·2,048 sqft
131 days on market
Listed by Rick Bavec, TOLARIS REALTY GROUP LLC
$599,000
1946 STRATHAVEN RD
WINTER PARK, 32792
4 bd·3 ba·2,102 sqft
104 days on market
Listed by Youbel Montesino, LPT REALTY, LLC
$450,000
316 BECKETT CT
WINTER PARK, 32792
4 bd·2 ba·1,651 sqft
104 days on market
Listed by Patrick Westervelt, LLC, VINTAGE REALTY SOLUTIONS
$248,900
193 LEWFIELD CIR
WINTER PARK, 32792
2 bd·2.5 ba·1,300 sqft
91 days on market
Listed by Efrain Reyes, COLDWELL BANKER REALTY
$1,450,000
120 BROADVIEW AVE
WINTER PARK, 32789
98 days on market
Listed by David Murray, PROMAX PROPERTY SOLUTIONS
$1,250,000
120 BROADVIEW AVE
WINTER PARK, 32789
3 bd·2 ba·1,747 sqft
103 days on market
Listed by David Murray, PROMAX PROPERTY SOLUTIONS
$999,000
616 BRECHIN DR
WINTER PARK, 32792
4 bd·4.5 ba·2,638 sqft
63 days on market
Pool
Listed by Alison Mosley, PREMIER SOTHEBY'S INTL. REALTY
$650,000
300 CAROLINA AVE #402C
WINTER PARK, 32789
3 bd·2 ba·1,350 sqft
141 days on market
Listed by Erin Baker, FANNIE HILLMAN & ASSOCIATES
$350,000
700 MELROSE AVE #J24
WINTER PARK, 32789
1 bd·1 ba·987 sqft
127 days on market
Listed by Scott Butts, KIMBRIDGE REALTY, LLC
$225,000
2503 TAHOE CIR #2503
WINTER PARK, 32792
2 bd·2 ba·1,173 sqft
89 days on market
Listed by KELLER WILLIAMS WINTER PARK
$180,000
2923 ANTIQUE OAKS CIR #34
WINTER PARK, 32792
2 bd·2 ba·1,105 sqft
74 days on market
Listed by Steve Pugh, EXP REALTY LLC
$2,475,000
926 ENCLAVE PL
WINTER PARK, 32792
5 bd·4.5 ba·4,150 sqft
139 days on market
PoolNew construction
Listed by Laura Earl, CORCORAN PREMIER REALTY
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: August 30, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.