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432 listings in Winter Park
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Winter Park
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Listings
New
$499,000
2231 NAIRN DR
WINTER PARK, 32792
1,088 sqft
0 days on market
Listed by David Auerbach, PARK TOWN REAL ESTATE LLC
New
$499,000
230 STRATHY LN
WINTER PARK, 32792
920 sqft
0 days on market
Listed by David Auerbach, PARK TOWN REAL ESTATE LLC
$389,000
2033 CANNY CV
WINTER PARK, 32792
3 bd·2.5 ba·1,907 sqft
88 days on market
Listed by Monica Puche, LPT REALTY, LLC
$1,800,000
281 BREWER AVE
WINTER PARK, 32789
5 bd·4.5 ba·4,029 sqft
91 days on market
Pool
Listed by John Henthorn, HENTHORN REAL ESTATE
$1,275,000
240 KILLARNEY DR
WINTER PARK, 32789
3 bd·2.5 ba·1,329 sqft
11 days on market
Waterfront
Listed by PREMIER SOTHEBYS INT'L REALTY
$1,250,000
230 KILLARNEY DR
WINTER PARK, 32789
4 bd·1 ba·1,260 sqft
11 days on market
Waterfront
Listed by PREMIER SOTHEBYS INT'L REALTY
$395,000
2568 LOTAFUN AVE
WINTER PARK, 32789
3 bd·2 ba·1,201 sqft
56 days on market
Listed by Randall Wolber, Jr
$775,000
1562 ARBOR PARK DR
WINTER PARK, 32789
4 bd·2.5 ba·1,899 sqft
22 days on market
Listed by Abby Greenberg, COMPASS FLORIDA LLC
New
$335,000
2526 PASSAMONTE DR #10F
WINTER PARK, 32792
3 bd·2.5 ba·1,790 sqft
1 day on market
Listed by Kathi Thomas
$250,000
2487 HARBOUR WAY
WINTER PARK, 32792
3 bd·3 ba·1,803 sqft
98 days on market
Listed by Joel Garay, LOKATION
$1,875,000
922 N PENNSYLVANIA AVE
WINTER PARK, 32789
4 bd·4 ba·3,440 sqft
99 days on market
Listed by Mick Night, PREMIER SOTHEBY'S INTL. REALTY
New
$1,600,000
250 KILLARNEY
WINTER PARK, 32789
4 bd·3.5 ba·2,568 sqft
1 day on market
Pool
Listed by Nancy Rossman, FLORIDA PROPERTY SPECIALIST
$699,500
1418 LONE FEATHER TRL
WINTER PARK, 32792
4 bd·2.5 ba·2,197 sqft
80 days on market
Listed by Harif Hazera LLC, PREMIER SOTHEBY'S INTL. REALTY
$1,495,000
462 W LYMAN AVE
WINTER PARK, 32789
3 bd·2.5 ba·1,944 sqft
100 days on market
Listed by Mick Night, PREMIER SOTHEBY'S INTL. REALTY
$699,000
436 W SWOOPE AVE
WINTER PARK, 32789
4 bd·3.5 ba·2,602 sqft
39 days on market
Listed by Kim Griffin, RE/MAX EXCLUSIVE COLLECTION
$368,000
885 CARNATION DR
WINTER PARK, 32792
4 bd·2 ba·1,240 sqft
55 days on market
Pool
Listed by Tashania Brown, RADIUS REALTY GROUP LLC
$1,995,000
1415 GROVE TER
WINTER PARK, 32789
91 days on market
Waterfront
$250,000
2450 GRAND TETON CIR #2450
WINTER PARK, 32792
3 bd·2 ba·1,311 sqft
53 days on market
Listed by John Campese, CHARLES RUTENBERG REALTY ORLANDO
$2,500,000
1477 W FAIRBANKS AVE
WINTER PARK, 32789
6,049 sqft
91 days on market
Listed by Sharon Helsby, FANNIE HILLMAN & ASSOCIATES
$549,900
1003 LAKE BELL DR
WINTER PARK, 32789
3 bd·2 ba·1,837 sqft
79 days on market
Waterfront
Listed by Bryan Douglas, KELLER WILLIAMS REALTY AT THE PARKS
$430,000
2041 JEWELL AVE
WINTER PARK, 32789
3 bd·1 ba·1,508 sqft
95 days on market
Listed by Martha Coronel, IAD REAL ESTATE
$2,549,000
1823 SUNSET DR
WINTER PARK, 32789
5 bd·4.5 ba·3,479 sqft
104 days on market
PoolNew construction
Listed by Christopher Christensen, ONE LUXURY INTERNATIONAL LLC
$190,000
1250 S DENNING DR #109
WINTER PARK, 32789
1 bd·1 ba·658 sqft
27 days on market
$275,000
5184 LAZY OAKS DR
WINTER PARK, 32792
2 bd·2 ba·1,008 sqft
44 days on market
Listed by Joyce Gary, PAINE-ANDERSON PROPERTIES, INC
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: July 22, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.