Homes for sale in Winter Park.
358 active listings in Winter Park, FL — live Stellar MLS inventory.
Communities in Winter Park
60 subdivisions with active listings
Listings in Winter Park
See all →
$7,250,000
40 Palmer Ave
Winter Park, FL 32789
5 bd · 6 ba · 5,905 sqft
Robert Dhu Macdonald Park
MLS ID #O6380444, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$6,900,000
1260 Alabama Dr
Winter Park, FL 32789
6 bd · 7 ba · 6,396 sqft
J Kronenberger Sub
MLS ID #O6387200, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$6,000,000
1571 Woodland Ave
Winter Park, FL 32789
5 bd · 8 ba · 7,397 sqft
Comstock Park
MLS ID #O6411706, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$5,600,000
2228 Azalea Pl
Winter Park, FL 32789
5 bd · 6 ba · 5,152 sqft
Maitland Shores First Add
MLS ID #O6416342, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$5,500,000
313 Sylvan Dr
Winter Park, FL 32789
4 bd · 5 ba · 4,775 sqft
Sylvan Park
MLS ID #O6407606, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$4,950,000
231 Chelton Cir
Winter Park, FL 32789
4 bd · 7 ba · 5,550 sqft
Forest Hills
MLS ID #O6414890, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.
Listing provided by Stellar MLS
$4,650,000
857 Brock St
Winter Park, FL 32789
5 bd · 6 ba · 4,827 sqft
Park Grove
MLS ID #O6432219, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$4,600,000
540 N Pennsylvania Ave
Winter Park, FL 32789
0.45 acres
Winter Park
MLS ID #O6431538, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$4,595,000
1525 Granville Dr
Winter Park, FL 32789
5 bd · 6 ba · 5,211 sqft
Park Grove
MLS ID #O6422951, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$4,500,000
503 N Interlachen Ave
Winter Park, FL 32789
0.48 acres
Winter Park
MLS ID #O6331207, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$4,299,000
2403 Euston Rd
Winter Park, FL 32789
8.23 acres
Justamere Camp Rep
MLS ID #O6434678, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$4,250,000
229 Alexander Pl
Winter Park, FL 32789
4 bd · 6 ba · 4,431 sqft
Alexander Place
MLS ID #O6412911, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of August 30, 2026 at 2:07 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA