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
$435,000
2020 Portcastle Cir
Winter Garden, FL 34787
3 bd · 3 ba · 1,857 sqft
Stone Crk A-1 & A-2
MLS ID #O6446086, EXP REALTY LLC.
Listing provided by Stellar MLS
$155,000
Winter Garden, FL 34787
2 bd · 2 ba · 1,265 sqft
Grove Residence & Spa Hotel Condo Ii
MLS ID #O6456209, WELCOME HOME REALTY GROUP LLC.
Listing provided by Stellar MLS
$369,000
14169 Avenue Of The Grvs
Winter Garden, FL 34787
2 bd · 3 ba · 1,476 sqft
Signature Lks-Pcl 01d Ph 01
MLS ID #O6444697, THE SIMON SIMAAN GROUP.
Listing provided by Stellar MLS
$20,000
Killarney Cove Dr
Oakland, FL 34787
0.28 acres
MLS ID #O6456042, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$20,000
Killarney Cove Dr
Oakland, FL 34787
0.28 acres
MLS ID #O6456041, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$20,000
Killarney Cove Dr
Oakland, FL 34787
0.28 acres
MLS ID #O6456040, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$60,000
Killarney Cove Dr
Oakland, FL 34787
0.84 acres
MLS ID #O6456035, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$265,000
1351 & 1359 Avalon Rd
Winter Garden, FL 34787
0.46 acres
MLS ID #TB8565873, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$375,000
6208 Aralia Ivy Ln
Winter Garden, FL 34787
3 bd · 3 ba · 1,560 sqft
Hamilton Gardens
MLS ID #O6427212, WEICHERT REALTORS HALLMARK PROPERTIES.
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
$489,990
15111 Groveside Rd
Winter Garden, FL 34787
3 bd · 3 ba · 1,846 sqft
Parkview At Hamlin
MLS ID #O6423268, DRB GROUP REALTY, LLC.
Listing provided by Stellar MLS
$165,000
14501 Grove Resort Ave #3239
Winter Garden, FL 34787
2 bd · 2 ba · 1,375 sqft
Grove Resort And Spa Hotel Condominium
MLS ID #S5160379, FLARE PROPERTIES LLC.
Listing provided by Stellar MLS
$283,800
14501 Grove Resort Ave #1516
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Resort And Spa Hotel
MLS ID #S5160899, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$430,000
14501 Grove Resort Ave #3618
Winter Garden, FL 34787
3 bd · 3 ba · 1,544 sqft
Grove Resort And Spa Hotel
MLS ID #S5160518, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$247,990
14501 Grove Resort Ave #1535
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Resort And Spa Hotel Condominium 1
MLS ID #S5150001, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$249,000
14501 Grove Resort Ave #1203
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Resort And Spa Hotel Condominium
MLS ID #S5144506, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$241,000
14501 Grove Resort Ave #1443
Winter Garden, FL 34787
2 bd · 2 ba · 1,375 sqft
Grove Resort And Spa Hotel
MLS ID #S5144504, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$239,990
14501 Grove Resort Ave #3535
Winter Garden, FL 34787
2 bd · 2 ba · 1,434 sqft
Grove Resort And Spa Hotel Condominium 3
MLS ID #S5138632, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$235,100
14501 Grove Resort Ave #1637
Winter Garden, FL 34787
2 bd · 2 ba · 1,375 sqft
Grove Resort And Spa Hotel Condominium 1
MLS ID #S5095151, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$279,000
15613 Boggy Oak Cir #110a
Winter Garden, FL 34787
2 bd · 2 ba · 1,216 sqft
Tucker Oaks Condo
MLS ID #O6450253, COLEDEV REAL ESTATE LLC.
Listing provided by Stellar MLS
$195,000
14501 Grove Resort Ave #2223
Winter Garden, FL 34787
2 bd · 2 ba · 1,265 sqft
Grove Resort And Spa Hotel
MLS ID #S5144425, SACKS REALTY GROUP, INC..
Listing provided by Stellar MLS
$299,900
14813 Strahan Blvd
Winter Garden, FL 34787
1 acres
MLS ID #S5155609, FLORIDA REALTY RESULTS LLC.
Listing provided by Stellar MLS
$230,000
14501 Grove Resort Ave #3424
Winter Garden, FL 34787
2 bd · 2 ba · 1,375 sqft
Grove Residence & Spa Hotel Condo 3
MLS ID #S5141575, EXP REALTY LLC.
Listing provided by Stellar MLS
$489,900
13151 Calming Breeze Way
Winter Garden, FL 34787
3 bd · 3 ba · 2,096 sqft
Serenade/Ovation Ph 1
MLS ID #O6455019, REDFIN CORPORATION.
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 November 10, 2026 at 8:18 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