Winter Garden Homes Under $500K for Sale
Every home priced under $500K currently for sale in Winter Garden — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Garden market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
24+ Homes Under $500K in the Winter Garden area
$215,000
14501 Grove Resort Ave #1528
Winter Garden, FL 34787
3 bd · 3 ba · 1,396 sqft
Grove Residence & Spa Hotel Condo I
MLS ID #O6451566, EXP REALTY LLC.
Listing provided by Stellar MLS
$409,000
15717 Kinnow Mandarin Ln
Winter Garden, FL 34787
3 bd · 3 ba · 1,868 sqft
Highlands/Summerlake Grvs Ph I
MLS ID #S5158170, REALTY HUB.
Listing provided by Stellar MLS
$435,000
10606 Words Dr
Winter Garden, FL 34787
4 bd · 3 ba · 1,863 sqft
Storey Grove Ph 4
MLS ID #O6448083, C23 REALTY LLC.
Listing provided by Stellar MLS
$239,000
200 Southern Pecan Circle #206
Winter Garden, FL 34787
2 bd · 2 ba · 1,276 sqft
Southern Pines Condo
MLS ID #O6411162, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$425,000
17802 Jefferson St
Winter Garden, FL 34787
4 bd · 2 ba · 1,778 sqft
Edgewater Beach
MLS ID #O6428887, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$430,000
5545 Bowman Dr
Winter Garden, FL 34787
2 bd · 3 ba · 1,998 sqft
Overlook 2/Hamlin Ph 1 & 6
MLS ID #O6407484, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$179,000
14501 Grove Resort Ave #3401
Winter Garden, FL 34787
3 bd · 3 ba · 1,544 sqft
Grove Residence & Spa Hotel Condo Li
MLS ID #S5154833, FLARE PROPERTIES LLC.
Listing provided by Stellar MLS
$185,000
14501 Grove Resort Ave #2119
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Residence & Spa Hotel Condo Ii
MLS ID #S5154456, FLARE PROPERTIES LLC.
Listing provided by Stellar MLS
$215,000
14501 Grove Resort Ave #1310
Winter Garden, FL 34787
2 bd · 2 ba · 1,265 sqft
Grove Resort And Spa Hotel Condo
MLS ID #O6397317, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$485,000
14543 Golden Harbor Ln
Winter Garden, FL 34787
3 bd · 3 ba · 2,039 sqft
Watermark
MLS ID #O6433451, PREFERRED REAL ESTATE BROKERS.
Listing provided by Stellar MLS
$495,000
13879 Lanyard Way
Winter Garden, FL 34787
3 bd · 3 ba · 1,983 sqft
Encore/Ovation Ph 3
MLS ID #G5115521, LPT REALTY, LLC.
Listing provided by Stellar MLS
$419,000
10534 Tribute Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,636 sqft
Storey Grove Ph 4
MLS ID #O6345956, LEGACY PLUS REALTY.
Listing provided by Stellar MLS
$399,000
11120 Suspense Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,636 sqft
Storey Grove Ph 1b-1
MLS ID #O6443446, ALLIVE REALTY.
Listing provided by Stellar MLS
$487,500
12086 Shine View Ln
Winter Garden, FL 34787
3 bd · 3 ba · 1,817 sqft
Waterleigh
MLS ID #O6436174, DR HORTON REALTY OF CENTRAL FLORIDA LLC.
Listing provided by Stellar MLS
$499,900
14099 Frasier St
Winter Garden, FL 34787
3 bd · 3 ba · 2,206 sqft
Highland Rdg Ph 2
MLS ID #S5155066, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$188,000
93 Windtree Ln #102
Winter Garden, FL 34787
2 bd · 2 ba · 918 sqft
Windtree Gardens
MLS ID #O6426740, REVEL REALTY LLC.
Listing provided by Stellar MLS
$369,900
15510 Campden St
Winter Garden, FL 34787
3 bd · 3 ba · 1,924 sqft
Stoneybrook West I
MLS ID #S5154448, MULTI CHOICE REALTY LLC.
Listing provided by Stellar MLS
$165,000
14501 Grove Resort Ave #2604
Winter Garden, FL 34787
2 bd · 2 ba · 1,375 sqft
Grove Residence & Spa Hotel Condo Ii
MLS ID #O6367873, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.
Listing provided by Stellar MLS
$395,000
10114 Salt Point Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,626 sqft
Waterleigh Ph 2e
MLS ID #O6447275, KELLER WILLIAMS ADVANTAGE 2 REALTY.
Listing provided by Stellar MLS
$483,500
15877 Tollington Aly
Winter Garden, FL 34787
3 bd · 3 ba · 1,835 sqft
Encore/Ovation Ph 4b
MLS ID #O6427665, RE/MAX SELECT GROUP.
Listing provided by Stellar MLS
$398,000
16306 Prairie School Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,792 sqft
Hawksmoor
MLS ID #O6433563, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$379,000
1221 Priory Cir
Winter Garden, FL 34787
3 bd · 3 ba · 1,675 sqft
Stoneybrook West I
MLS ID #S5155802, AROD PARTNERS REALTY.
Listing provided by Stellar MLS
$449,990
7276 Windy Willow St
Winter Garden, FL 34787
3 bd · 3 ba · 1,764 sqft
Hamlin Meadows
MLS ID #G5115862, OLYMPUS EXECUTIVE REALTY INC.
Listing provided by Stellar MLS
$454,990
7272 Windy Willow St
Winter Garden, FL 34787
3 bd · 3 ba · 1,697 sqft
Hamlin Meadows
MLS ID #G5115861, OLYMPUS EXECUTIVE REALTY INC.
Listing provided by Stellar MLS
More Winter Garden Homes for Sale
All Winter Garden 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 1:01 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