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432 listings in Winter Park
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Winter Park
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Listings
New
$1,350,000
1320 ORCHID AVE
WINTER PARK, 32789
4 bd·4 ba·2,998 sqft
1 day on market
Listed by Isis Sarcos, EXP REALTY LLC
$1,295,000
720 PANSY AVE
WINTER PARK, 32789
3 bd·4 ba·2,191 sqft
49 days on market
Listed by Nick McKee, KELLER WILLIAMS WINTER PARK
$739,777
4039 COOL WATER CT
WINTER PARK, 32792
4 bd·2 ba·2,267 sqft
43 days on market
Pool
Listed by Karen Arbutine, RE/MAX CENTRAL REALTY
$699,000
1850 BRYAN AVE
WINTER PARK, 32789
3 bd·2 ba·1,563 sqft
49 days on market
Listed by Jennifer King, CORCORAN PREMIER REALTY
New
$365,000
7506 CRANES CREEK CT #30
WINTER PARK, 32792
3 bd·2.5 ba·1,861 sqft
1 day on market
Listed by Sylvia Marchese, TRANSCONTINENTAL REALTY GROUP,
$220,000
1810 STATE ROAD 436
WINTER PARK, 32792
15,232 sqft
40 days on market
Listed by Kyler Moreland, REMAX SUNSTATE REALTY
$159,900
3651 N GOLDENROD RD #C205
WINTER PARK, 32792
2 bd·2 ba·840 sqft
10 days on market
Listed by Hitesh Khatri, CFRP REALTY LLC
$285,000
2657 EXUMA WAY
WINTER PARK, 32792
3 bd·2 ba·1,467 sqft
21 days on market
Listed by Jerry Agan, HAVEN PROPERTY GROUP LLC
$255,000
5108 LAZY OAKS DR #5108
WINTER PARK, 32792
2 bd·2 ba·1,008 sqft
39 days on market
Listed by Steven Koleno, BEYCOME OF FLORIDA LLC
$575,000
1259 INDIANA AVE
WINTER PARK, 32789
2 bd·2.5 ba·1,648 sqft
51 days on market
Listed by Karan Wienker, COLDWELL BANKER REALTY
$950,000
1220 HOWELL BRANCH RD
WINTER PARK, 32789
3 bd·2 ba·1,487 sqft
44 days on market
Listed by Fook Snipper, PARK PLACE REAL ESTATE
$950,000
471 HOLT AVE
WINTER PARK, 32789
4 bd·3 ba·2,528 sqft
41 days on market
Listed by Tina Bollet, FLORIDA HOME TEAM REALTY LLC
$269,000
151 N ORLANDO AVE #242
WINTER PARK, 32789
2 bd·1 ba·710 sqft
29 days on market
Waterfront
Listed by COLONIALTOWN REALTY
$1,550,000
2430 CHANTILLY AVE
WINTER PARK, 32789
4 bd·4 ba·2,916 sqft
55 days on market
PoolNew construction
Listed by Kelly Price, KELLY PRICE & COMPANY LLC
$1,600,000
2207 KINDEL AVE
WINTER PARK, 32789
3 bd·2.5 ba·2,733 sqft
50 days on market
Listed by Sandra Velasquez, THE SIMON SIMAAN GROUP
No photo
New
$849,999
724 MONMOUTH WAY
WINTER PARK, 32792
5 bd·3.5 ba·2,832 sqft
0 days on market
$3,265,000
1761 LEGION DR
WINTER PARK, 32789
5 bd·5.5 ba·4,949 sqft
46 days on market
Pool
Listed by Harry Pool, III, COLDWELL BANKER REALTY
$1,875,000
751 PANSY AVE
WINTER PARK, 32789
3 bd·3.5 ba·2,703 sqft
52 days on market
Pool
Listed by Julie Christensen, ONE LUXURY INTERNATIONAL LLC
$3,600,000
276 DETMAR DR
WINTER PARK, 32789
4 bd·5 ba·4,202 sqft
3 days on market
Pool
Listed by Melanie Johnston, CALL IT CLOSED INTL REALTY
$1,829,000
1550 PALM AVE
WINTER PARK, 32789
4 bd·3.5 ba·2,706 sqft
39 days on market
PoolNew construction
Listed by Brian Mitnik, RE/MAX 200 REALTY
$242,500
1250 S DENNING DR #Unit 233
WINTER PARK, 32789
2 bd·2 ba·913 sqft
49 days on market
Pool
Listed by STOCKWORTH REALTY GROUP
New
$189,900
222 LEWFIELD CIR
WINTER PARK, 32792
2 bd·2 ba·953 sqft
1 day on market
Listed by Joshua Neudigate, MARKET CONNECT REALTY LLC
$4,299,000
2403 EUSTON RD
WINTER PARK, 32789
53 days on market
Listed by Marie Helen Ledbetter, COLDWELL BANKER REALTY
$1,299,000
1445 VIA SANGRO PL
WINTER PARK, 32792
6 bd·5.5 ba·5,021 sqft
42 days on market
Pool
Listed by Suzanne Seenandan, PREFERRED RE BROKERS III
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: September 4, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.