Winter Park Luxury Homes for Sale
Every luxury home currently for sale in Winter Park — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Park market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
24+ Luxury Homes in the Winter Park area
$1,800,000
281 Brewer Ave
Winter Park, FL 32789
5 bd · 5 ba · 4,029 sqft
Osceola Shores Sec 02
MLS ID #O6424364, HENTHORN REAL ESTATE.
Listing provided by Stellar MLS
$1,999,900
240 N Phelps Ave
Winter Park, FL 32789
5 bd · 5 ba · 2,889 sqft
Sylvan Heights
MLS ID #O6415360, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$2,100,000
Winter Park, FL 32789
4 bd · 5 ba · 2,830 sqft
Lake Killarney Shores
MLS ID #O6456614, PLATINUM REALTY GROUP FLORIDA INC.
Listing provided by Stellar MLS
$1,429,900
1546 Miller Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,984 sqft
Lawndale
MLS ID #O6428019, RE/MAX EXCLUSIVE COLLECTION.
Listing provided by Stellar MLS
$1,850,000
2507 Lafayette Ave
Winter Park, FL 32789
4 bd · 6 ba · 2,675 sqft
Winter Park Village
MLS ID #O6450302, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$6,795,000
901 Golfview Ter
Winter Park, FL 32789
5 bd · 6 ba · 5,479 sqft
Golfview Terrace
MLS ID #O6437917, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$2,500,000
1760 Oakhurst Ave
Winter Park, FL 32789
5 bd · 5 ba · 3,700 sqft
Jenkins Second Add
MLS ID #O6441988, SIERRA REALTY GROUP LLC.
Listing provided by Stellar MLS
$1,949,000
1398 Grove Ter
Winter Park, FL 32789
4 bd · 4 ba · 3,450 sqft
Sylvan Lake Shores
MLS ID #O6454512, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$1,949,000
1951 Winter Park Rd
Winter Park, FL 32789
4 bd · 4 ba · 3,479 sqft
Charmont
MLS ID #O6441816, KELLER WILLIAMS WINTER PARK.
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
$1,599,000
533 Country Club Dr
Winter Park, FL 32789
4 bd · 4 ba · 2,942 sqft
Lake Killarney Shores
MLS ID #O6440841, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$2,750,000
1663 N Park Ave
Winter Park, FL 32789
4 bd · 5 ba · 3,640 sqft
Dixie Terrace
MLS ID #O6453687, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$1,100,000
531 Worthington Dr
Winter Park, FL 32789
3 bd · 3 ba · 2,626 sqft
Kenilworth Shores
MLS ID #O6455524, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$1,425,000
1581 Magnolia Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,642 sqft
Lake Knowles Terrace Add 02
MLS ID #O6396118, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,149,000
1824 Jessica Ct
Winter Park, FL 32789
4 bd · 3 ba · 2,582 sqft
Waterbridge
MLS ID #O6452920, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$1,675,000
2343 Versailles Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,307 sqft
Fontainebleau
MLS ID #O6432029, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$3,195,000
1825 Whitehall Dr
Winter Park, FL 32789
4 bd · 6 ba · 4,311 sqft
Kenilworth Shores Sec 06
MLS ID #O6450811, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$2,350,000
200 S Interlachen Ave #350
Winter Park, FL 32789
3 bd · 4 ba · 3,110 sqft
Versailles Winter Park Condo
MLS ID #O6438596, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$2,629,000
1681 Woodland Ave
Winter Park, FL 32789
5 bd · 5 ba · 3,682 sqft
Comstock Park
MLS ID #O6449440, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,369,000
1473 Berkshire Ave
Winter Park, FL 32789
5 bd · 4 ba · 2,446 sqft
Orwin Manor Westminster Sec
MLS ID #O6415098, KARDOSH REALTY.
Listing provided by Stellar MLS
$1,295,000
720 Pansy Ave
Winter Park, FL 32789
3 bd · 4 ba · 2,191 sqft
Villa View Park
MLS ID #O6434255, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$1,399,900
1737 Indiana Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,984 sqft
Lawndale
MLS ID #S5158760, LOKATION.
Listing provided by Stellar MLS
$1,425,000
100 S Virginia Ave #201
Winter Park, FL 32789
3 bd · 3 ba · 2,756 sqft
Winter Park Residential
MLS ID #O6442678, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$1,775,000
101 S New York Ave #311
Winter Park, FL 32789
3 bd · 4 ba · 3,112 sqft
Winter Park Residential
MLS ID #O6416927, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
More Winter Park Homes for Sale
All Winter Park homes $500K and up, with the live market brief →
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 November 11, 2026 at 6:02 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