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432 listings in Winter Park
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Winter Park
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Listings
$849,000
437 N CAPEN AVE
WINTER PARK, 32789
3 bd·2.5 ba·1,904 sqft
70 days on market
Listed by Brandon Geers, COMPASS FLORIDA LLC
$470,000
2008 HOUNDSLAKE DR
WINTER PARK, 32792
4 bd·2 ba·2,250 sqft
127 days on market
Listed by Nicholas Feinsod, MARK SPAIN REAL ESTATE
$374,900
1840 ASTER DR
WINTER PARK, 32792
3 bd·2 ba·1,666 sqft
119 days on market
Listed by KONA REALTY SERVICES LLC
$2,995,000
1836 WHITEHALL DR
WINTER PARK, 32789
5 bd·6.5 ba·4,168 sqft
110 days on market
PoolNew construction
Listed by Bianca Khoury, PREMIER SOTHEBY'S INTL. REALTY
$1,999,900
240 N PHELPS AVE
WINTER PARK, 32789
5 bd·4.5 ba·2,889 sqft
125 days on market
PoolNew construction
Listed by Nick McKee, KELLER WILLIAMS WINTER PARK
$1,595,000
1113 VIA DEL MAR
WINTER PARK, 32789
39 days on market
Waterfront
Listed by David Barany
$774,900
1265 ARLINGTON PL
WINTER PARK, 32789
3 bd·3.5 ba·2,030 sqft
118 days on market
Listed by FANNIE HILLMAN & ASSOCIATES
$4,700,000
231 CHELTON CIR
WINTER PARK, 32789
4 bd·6 ba·5,550 sqft
118 days on market
Pool
Listed by Joseph Doher, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
$1,369,000
1473 BERKSHIRE AVE
WINTER PARK, 32789
5 bd·4 ba·2,446 sqft
132 days on market
PoolNew construction
Listed by KARDOSH REALTY
$242,400
2500 LEE RD #104
WINTER PARK, 32789
2 bd·2 ba·956 sqft
96 days on market
Listed by Stephen Hachey, FLAT FEE MLS REALTY
$199,900
2500 LEE RD #220
WINTER PARK, 32789
2 bd·1 ba·851 sqft
7 days on market
Listed by Thomas Nickley, Jr, KELLER WILLIAMS REALTY AT THE PARKS
$2,995,000
125 S INTERLACHEN AVE #2
WINTER PARK, 32789
3 bd·4 ba·3,244 sqft
71 days on market
Listed by Erin Legler, CHARLES RUTENBERG REALTY ORLANDO
$1,800,000
2032 KIMBRACE PL
WINTER PARK, 32792
5 bd·4 ba·3,382 sqft
65 days on market
Pool
Listed by Robert Sassos, SIMPLICITY: A RE BROKERAGE CO
$494,900
2715 PRINCE JOHN RD
WINTER PARK, 32792
3 bd·2 ba·1,565 sqft
43 days on market
Listed by Donna Peebles, VIA PROPERTIES LLC
$1,499,000
641 NORTHWOOD CIRCLE
WINTER PARK, 32789
3 bd·4 ba·2,756 sqft
135 days on market
Pool
Listed by Sandra Cuba, PREMIER SOTHEBY'S INTL. REALTY
$695,000
2831 MULFORD AVE
WINTER PARK, 32789
4 bd·2.5 ba·1,647 sqft
109 days on market
Listed by Patrick Arenson, UNITED REAL ESTATE PREFERRED
$2,625,000
413 W MORSE BLVD
WINTER PARK, 32789
3 bd·3.5 ba·3,048 sqft
114 days on market
Listed by AV Blalock, COLDWELL BANKER REALTY
$3,500,000
2240 VENETIAN WAY
WINTER PARK, 32789
4 bd·3.5 ba·4,036 sqft
46 days on market
WaterfrontPool
Listed by Johnny Hurlburt, COLDWELL BANKER REALTY
$649,900
840 W CANTON AVE
WINTER PARK, 32789
3 bd·2 ba·1,370 sqft
66 days on market
Listed by Ken Pozek, REAL BROKER, LLC
$535,000
1250 FORMOSA AVE
WINTER PARK, 32789
3 bd·3.5 ba·1,937 sqft
136 days on market
Listed by Jeanine Louis, LLC, EXP REALTY LLC
$399,900
5503 ALBERT DR
WINTER PARK, 32792
3 bd·2 ba·1,366 sqft
96 days on market
Listed by AXEN REALTY LLC
$3,500,000
649 N PARK AVE
WINTER PARK, 32789
3 bd·4 ba·3,180 sqft
11 days on market
Listed by Drew Henner, PREMIER SOTHEBY'S INTL. REALTY
$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
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: August 24, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.