Homes for sale in Winter Park.
333 active listings in Winter Park, FL — live Stellar MLS inventory.
Communities in Winter Park
60 subdivisions with active listings
Listings in Winter Park
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$8,950,000
1120 Preserve Point Dr
Winter Park, FL 32789
7 bd · 11 ba · 11,255 sqft
Windsong-Preserve Point
MLS ID #O6350054, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$6,950,000
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
$6,495,000
550 Palmer Ave
Winter Park, FL 32789
5 bd · 7 ba · 5,939 sqft
Osceola Place
MLS ID #O6349188, FANNIE HILLMAN & ASSOCIATES.
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
$5,995,000
1200 Via Salerno
Winter Park, FL 32789
5 bd · 6 ba · 5,476 sqft
Cloister Grove Sub
MLS ID #O6381761, PREMIER SOTHEBY'S INTL. REALTY.
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
$5,250,000
2211 Azalea Pl
Winter Park, FL 32789
5 bd · 7 ba · 7,278 sqft
Maitland Shores
MLS ID #O6319674, FORTUNE INTERNATIONAL 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
$4,500,000
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
$4,295,000
643 N Park Ave
Winter Park, FL 32789
3 bd · 5 ba · 4,231 sqft
Park Hill
MLS ID #O6403591, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$4,285,000
1441 Cardinal Ct
Winter Park, FL 32789
4 bd · 6 ba · 4,066 sqft
Winflor Court Pt Rep
MLS ID #O6399395, CHARLES RUTENBERG REALTY ORLANDO.
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 June 19, 2026 at 1:03 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA