Winter Garden Homes for Sale Under $300K
Homes, condos and townhomes listed at $300,000 or less.
- For sale now
- 105
- Median list price
- $217K
- Median $ / sq ft
- $175
- Median days listed
- 148
Newest 24 of 105 homes under $300k in Winter Garden
$185,000
14200 Avalon Rd #409
Winter Garden, FL 34787
2 bd · 2 ba · 1,253 sqft
Palisades
MLS ID #O6410860, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$235,000
1229 Winter Green Way
Winter Garden, FL 34787
2 bd · 2 ba · 1,144 sqft
Village Grove Ph 02
MLS ID #A4712547, REDFIN CORPORATION.
Listing provided by Stellar MLS
$210,000
421 Eron Way #36
Winter Garden, FL 34787
2 bd · 2 ba · 930 sqft
Townhomes Winter Garden
MLS ID #O6456332, HOMEVEST REALTY.
Listing provided by Stellar MLS
$300,000
14501 Grove Resort Ave #1603
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Residence & Spa Hotel Condo I
MLS ID #O6357304, SUNSHINE REALTY & PROP. MGNT.
Listing provided by Stellar MLS
$179,000
87 Windtree Ln #K
Winter Garden, FL 34787
2 bd · 2 ba · 918 sqft
Windtree Gardens Condo Ph 03
MLS ID #O6450975, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$208,000
1451 E Bay St
Winter Garden, FL 34787
3 bd · 1 ba · 1,139 sqft
Joe Louis Park
MLS ID #O6456697, HOMEVEST REALTY.
Listing provided by Stellar MLS
$130,000
386 Railroad Ave
Winter Garden, FL 34787
2 bd · 1 ba · 660 sqft
Loveless & Sewell
MLS ID #O6456566, ORANGE REALTY MASTERS.
Listing provided by Stellar MLS
$217,000
988 Stucki Ter
Winter Garden, FL 34787
3 bd · 2 ba · 1,216 sqft
Westside Townhomes Phase 2 19/100 Lot 5 Blk 11
MLS ID #TB8539994, BEACHFRONT REALTY INC.
Listing provided by Stellar MLS
$174,900
14501 Grove Resort Ave #3438
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Residence & Spa Hotel Condo Il
MLS ID #O6434706, ACME REAL ESTATE FLORIDA 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
$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
$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
$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
$180,000
14501 Grove Resort Ave #2616
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Residence & Spa Hotel Condo Ii
MLS ID #O6406283, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.
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
$250,000
14501 Grove Resort Ave #3211
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Resort And Spa
MLS ID #O6408877, UNITED REALTY GROUP INC.
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
$169,000
14501 Grove Resort Ave #3406
Winter Garden, FL 34787
2 bd · 2 ba · 1,265 sqft
Grove Residence & Spa Hotel Condo 3
MLS ID #S5154450, FLARE PROPERTIES 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
$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
$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
Search all Winter Garden listings on the map →
Winter Garden homes under $300k by price
- Under $300K104
- $300K–$500K1
Neighborhoods with the most homes under $300k for sale
- Grove Resort And Spa Hotel Condominium16 listed
- Grove Residence & Spa Hotel Condo14 listed
- Grove Residence & Spa Hotel Condo Ii13 listed
- Grove Resort And Spa Hotel Condo8 listed
- Southern Pines Condo8 listed
- Townhomes Winter Garden5 listed
- Grove Residence & Spa Hotel Condo I4 listed
- Palisades3 listed
- Windtree Gardens Condo3 listed
- Grove Resort And Spa Hotel3 listed
Winter Garden homes under $300k: quick answers
How many homes under $300k are for sale in Winter Garden?+
105 homes under $300k are listed for sale in Winter Garden, FL right now, 7 of them new in the last 7 days. Homes, condos and townhomes listed at $300,000 or less.
What do homes under $300k cost in Winter Garden?+
The median list price is $217K (about $175 per square foot), with listings from $130K to $300K.
How long do homes under $300k in Winter Garden stay on the market?+
The listings for sale now have been on the market a median of 148 days.
Which Winter Garden neighborhoods have the most homes under $300k for sale?+
Grove Resort And Spa Hotel Condominium (16), Grove Residence & Spa Hotel Condo (14), Grove Residence & Spa Hotel Condo Ii (13), Grove Resort And Spa Hotel Condo (8), Southern Pines Condo (8).
More Winter Garden homes for sale
Homes Under $300K in other cities
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 13, 2026 at 9:57 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.
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