Winter Park, FL Homes For Sale
470 listings. Live MLS data, refreshed nightly. Winter Park market overview
Winter Park, FL
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Listings
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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
$625,000
1016 ARAGON AVE
WINTER PARK, 32789
4 bd·3 ba·1,840 sqft
45 days on market
Pool
Listed by Pam Stewart, PALMANO GROUP RE BROKERAGE LLC
$419,990
2181 LINDEN RD
WINTER PARK, 32792
5 bd·3 ba·1,442 sqft
32 days on market
Listed by Paula Chavez, KELLER WILLIAMS ADVANTAGE III
$279,000
283 SANDLEWOOD TRL #3
WINTER PARK, 32789
2 bd·2.5 ba·960 sqft
58 days on market
Listed by Crystal Adams, PA, RE/MAX INNOVATION
$1,449,000
150 E READING WAY
WINTER PARK, 32789
3 bd·2.5 ba·2,080 sqft
8 days on market
Listed by Wendy Williams Crumit, FANNIE HILLMAN & ASSOCIATES
$625,000
1016 ARAGON AVE
WINTER PARK, 32789
4 bd·1,840 sqft
45 days on market
Pool
Listed by Pam Stewart, PALMANO GROUP RE BROKERAGE LLC
$659,000
900 CARVER ST
WINTER PARK, 32789
3 bd·3 ba·1,794 sqft
61 days on market
Listed by Farhad Haniff, EXP REALTY LLC
$349,000
7605 ALOMA PINES CT
WINTER PARK, 32792
3 bd·2.5 ba·1,872 sqft
41 days on market
Listed by Simon Colak
$925,000
311 E MORSE BLVD #4-5
WINTER PARK, 32789
2 bd·2 ba·1,763 sqft
35 days on market
Listed by Kim Garcia, KELLER WILLIAMS ADVANTAGE REALTY
$879,000
1621 CHESTNUT AVE
WINTER PARK, 32789
3 bd·2.5 ba·2,022 sqft
43 days on market
Listed by Kelly Price, KELLY PRICE & COMPANY LLC
$575,000
7525 LODGE POLE TRL
WINTER PARK, 32792
4 bd·2 ba·1,936 sqft
45 days on market
Pool
Listed by Amy Turner, KELLER WILLIAMS WINTER PARK
$229,999
151 N ORLANDO AVE #261
WINTER PARK, 32789
1 bd·1 ba·582 sqft
26 days on market
Listed by Nikita Ager, LLC, FLORIDA REALTY INVESTMENTS
$194,900
623 GRENADINE CT #623
WINTER PARK, 32792
2 bd·2 ba·1,037 sqft
26 days on market
Listed by Carolyn Kickhofel, COLDWELL BANKER REALTY
$147,000
285 LEWFIELD CIR #285
WINTER PARK, 32792
1 bd·1 ba·678 sqft
40 days on market
Listed by Millie Soto, COLDWELL BANKER REALTY
$1,999,900
1133 BELLA LAGO CV
WINTER PARK, 32792
33 days on market
Waterfront
Listed by Hang Kendall, LPT REALTY, LLC
$139,998
3019 ANTIQUE OAKS CIR #127
WINTER PARK, 32792
1 bd·1 ba·749 sqft
48 days on market
Listed by Steven Koleno, BEYCOME OF FLORIDA LLC
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: August 28, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.