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
$1,049,000
1517 Harmon Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,135 sqft
Lawndale
MLS ID #O6443217, BEYCOME OF FLORIDA LLC.
Listing provided by Stellar MLS
$4,500,000
1631 Hillcrest Ave
Winter Park, FL 32789
5 bd · 6 ba · 4,754 sqft
Ellno Willo
MLS ID #O6443872, CHRIS QUARLES PROPERTIES LLC.
Listing provided by Stellar MLS
$3,390,000
1751 Glencoe Rd
Winter Park, FL 32789
5 bd · 7 ba · 4,520 sqft
Forest Hills
MLS ID #O6442410, ONE LUXURY INTERNATIONAL LLC.
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
$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
$1,419,900
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
$3,495,000
1600 Legion Dr
Winter Park, FL 32789
5 bd · 6 ba · 4,483 sqft
Green Oaks Rep
MLS ID #O6450869, COLDWELL BANKER REALTY.
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
$3,250,000
2823 Parkland Circle
Winter Park, FL 32789
5 bd · 6 ba · 4,459 sqft
Lake Forest Park
MLS ID #O6444919, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,499,000
641 Northwood Circle
Winter Park, FL 32789
3 bd · 5 ba · 2,756 sqft
Winter Park Oasis
MLS ID #O6412554, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$6,195,000
698 N New York Ave
Winter Park, FL 32789
5 bd · 6 ba · 5,096 sqft
Greens/Pk
MLS ID #O6439388, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$6,995,000
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
$4,250,000
702 Via Bella
Winter Park, FL 32789
4 bd · 6 ba · 3,720 sqft
Palmer Ave Lakeside Prop
MLS ID #O6437125, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,875,000
922 N Pennsylvania Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,440 sqft
Tantum Add
MLS ID #O6424685, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,495,000
462 W Lyman Ave
Winter Park, FL 32789
3 bd · 3 ba · 1,944 sqft
Winter Park
MLS ID #O6423842, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$3,075,000
1821 Englewood Rd
Winter Park, FL 32789
5 bd · 6 ba · 3,863 sqft
Forest Hills
MLS ID #O6345085, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,450,000
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
$1,399,000
512 W Swoope Ave
Winter Park, FL 32789
3 bd · 3 ba · 2,585 sqft
Vilasa Twnhms
MLS ID #O6417375, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$1,890,000
2614 Parkland Dr
Winter Park, FL 32789
4 bd · 4 ba · 3,307 sqft
Parklando 03
MLS ID #O6444165, JW GASTON LLC.
Listing provided by Stellar MLS
$5,500,000
1166 Palmer Ave
Winter Park, FL 32789
5 bd · 7 ba · 5,181 sqft
Palmer Ave Lakeside Prop
MLS ID #O6442798, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$2,195,000
1271 Palmer Ave
Winter Park, FL 32789
4 bd · 5 ba · 2,850 sqft
J Kronenberger Sub
MLS ID #O6441038, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$1,095,000
1922 Hammerlin Ave
Winter Park, FL 32789
3 bd · 3 ba · 1,873 sqft
Edgewood Sub
MLS ID #O6439477, PALM PROPERTIES OF CF, INC..
Listing provided by Stellar MLS
$2,725,000
1773 Walnut Ave
Winter Park, FL 32789
5 bd · 5 ba · 3,784 sqft
Conwill Estates
MLS ID #O6437159, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,699,000
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
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 October 22, 2026 at 2:22 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