Winter Park, FL 32789 Homes For Sale
243 listings. Live MLS data, refreshed nightly. Winter Park market overview
32789
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Listings
New
$425,000
157 E NEW ENGLAND AVE #302
WINTER PARK, 32789
940 sqft
0 days on market
Listed by Dante Sandroni, SANDRONI HOLDINGS REAL ESTATE LLC
$745,000
408 HOLT AVE
WINTER PARK, 32789
2 bd·1,440 sqft
147 days on market
$2,500,000
450 LAKEWOOD DR
WINTER PARK, 32789
5 bd·5 ba·4,572 sqft
137 days on market
Pool
Listed by Vonda Fields, CHARLES RUTENBERG REALTY ORLANDO
$1,599,000
1864 GRINNELL TER
WINTER PARK, 32789
5 bd·3.5 ba·3,028 sqft
154 days on market
Pool
Listed by Robyn Brehne-Glass, COLDWELL BANKER REALTY
$1,495,000
446 MELROSE AVE
WINTER PARK, 32789
4 bd·2 ba·2,640 sqft
170 days on market
Listed by Audra Wilks, PREMIER SOTHEBY'S INTL. REALTY
$995,000
1611 CHESTNUT AVE
WINTER PARK, 32789
4 bd·4 ba·2,916 sqft
136 days on market
Listed by Olivia Maxwell, FANNIE HILLMAN & ASSOCIATES
$490,900
525 OLOLU DR
WINTER PARK, 32789
3 bd·3 ba·1,786 sqft
159 days on market
$999,000
726/720 N PENNSYLVANIA AVE
WINTER PARK, 32789
6 bd·2,282 sqft
166 days on market
Listed by Brandon Geers, COMPASS FLORIDA LLC
$2,399,000
2838 WRIGHT AVE
WINTER PARK, 32789
5 bd·4.5 ba·3,479 sqft
104 days on market
PoolNew construction
Listed by Mick Night, PREMIER SOTHEBY'S INTL. REALTY
$589,000
1319 BESSMOR RD
WINTER PARK, 32789
3 bd·2 ba·1,126 sqft
114 days on market
Listed by Sidney Galloway, GALLOWAY REAL ESTATE
$524,900
1741 WESTCHESTER AVE
WINTER PARK, 32789
3 bd·2 ba·1,434 sqft
165 days on market
Listed by Mick Night, PREMIER SOTHEBY'S INTL. REALTY
$320,000
811 OVERSPIN DR
WINTER PARK, 32789
2 bd·1 ba·749 sqft
180 days on market
Listed by Rick Singh, RICK SINGH REAL ESTATE
$3,995,000
1441 CARDINAL CT
WINTER PARK, 32789
4 bd·5.5 ba·4,066 sqft
137 days on market
Pool
Listed by Damian Bergler, CHARLES RUTENBERG REALTY ORLANDO
$1,049,000
2702 PARKLAND DR
WINTER PARK, 32789
5 bd·3 ba·2,656 sqft
163 days on market
$630,000
2600 EUSTON RD
WINTER PARK, 32789
6 bd·3 ba·3,145 sqft
151 days on market
Listed by AROD PARTNERS REALTY
$2,689,000
620 PINETREE RD
WINTER PARK, 32789
155 days on market
Listed by FANNIE HILLMAN & ASSOCIATES
$1,350,000
1881 LAKE SPIER DR
WINTER PARK, 32789
3 bd·2 ba·1,750 sqft
137 days on market
Waterfront
Listed by NOVA REAL ESTATE SERVICES INC
$1,350,000
1881 LAKE SPIER DR
WINTER PARK, 32789
137 days on market
Waterfront
Listed by NOVA REAL ESTATE SERVICES INC
$99,900
1695 LEE RD #D211
WINTER PARK, 32789
2 bd·1 ba·881 sqft
148 days on market
Listed by Brandy Ray, LOKATION
$1,250,000
1870 STAUNTON AVE
WINTER PARK, 32789
4 bd·3.5 ba·2,525 sqft
126 days on market
New construction
Listed by Vinny Lay, COMPASS FLORIDA LLC
$1,770,000
621 HUNTINGTON AVE
WINTER PARK, 32789
3 bd·3.5 ba·2,399 sqft
133 days on market
Pool
Listed by OLDE TOWN BROKERS INC
$1,485,000
1570 PALMER AVE
WINTER PARK, 32789
4 bd·3.5 ba·3,048 sqft
148 days on market
Pool
Listed by David Auerbach, PARK TOWN REAL ESTATE LLC
$1,750,000
1750 CAROLLEE LANE
WINTER PARK, 32789
4 bd·3.5 ba·3,249 sqft
183 days on market
Pool
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,649,000
1903 N PARK AVE
WINTER PARK, 32789
4 bd·4 ba·2,807 sqft
177 days on market
Pool
Listed by Chris Creegan, CREEGAN GROUP
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: May 11, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.