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 Winter Park
$2,995,000
1836 Whitehall Dr
Winter Park, FL 32789
5 bd · 7 ba · 4,168 sqft
Kenilworth Shores Sec 06
MLS ID #O6416158, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,598,000
2430 Chantilly Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,916 sqft
Winter Park Village
MLS ID #O6436367, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$2,050,000
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
$1,600,000
723 Symonds Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,065 sqft
Horton Aaron
MLS ID #O6406823, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$1,525,000
341 E Reading Way
Winter Park, FL 32789
4 bd · 4 ba · 3,723 sqft
Charmont
MLS ID #O6420387, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$4,350,000
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
$1,829,000
1550 Palm Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,706 sqft
Lake Knowles Terrace 2nd Add
MLS ID #O6436458, RE/MAX 200 REALTY.
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
$3,150,000
125 S Interlachen Ave #2
Winter Park, FL 32789
3 bd · 5 ba · 3,244 sqft
South Interlachen Place
MLS ID #O6411134, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$2,695,000
660 W Morse Blvd
Winter Park, FL 32789
3 bd · 4 ba · 3,286 sqft
Morse & Pennsylvania Twnhms
MLS ID #O6419377, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$1,495,000
446 Melrose Ave
Winter Park, FL 32789
4 bd · 2 ba · 2,640 sqft
Virginia Heights Rep
MLS ID #O6402113, PREMIER SOTHEBY'S INTL. REALTY.
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
$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
$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
$1,599,000
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
$2,549,000
1823 Sunset Dr
Winter Park, FL 32789
5 bd · 5 ba · 3,479 sqft
Lake Knowles Terrace Add 02
MLS ID #O6421690, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$3,195,000
2119 Howard Dr
Winter Park, FL 32789
5 bd · 6 ba · 4,139 sqft
Timberlane
MLS ID #O6442111, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$1,498,000
1841 Lake Spier Drive
Winter Park, FL 32789
3 bd · 4 ba · 2,467 sqft
South Lakemont Shores
MLS ID #O6407841, FANNIE HILLMAN & ASSOCIATES.
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
$1,250,000
120 Broadview Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,747 sqft
Killarney Estates
MLS ID #O6440960, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$1,450,000
120 Broadview Ave
Winter Park, FL 32789
0.23 acres
Killarney Estates
MLS ID #O6440974, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$2,089,000
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
$3,600,000
207 E Kings Way
Winter Park, FL 32789
5 bd · 5 ba · 3,719 sqft
Charmont
MLS ID #O6337304, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,750,000
1750 Carollee Lane
Winter Park, FL 32789
4 bd · 4 ba · 3,249 sqft
Green Terrace V/140 Lot 3 Blk B
MLS ID #O6391179, PREMIER SOTHEBY'S INTL. REALTY.
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 2, 2026 at 11:52 AM 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