Winter Haven Homes Under $500K for Sale
Every home priced under $500K currently for sale in Winter Haven — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Haven 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 Haven area
$284,500
2523 Avenue E Sw
Winter Haven, FL 33880
3 bd · 2 ba · 1,930 sqft
West Winter Haven
MLS ID #TB8530987, SIVEN PREMIER REAL ESTATE.
Listing provided by Stellar MLS
$274,500
2519 Avenue E Sw
Winter Haven, FL 33880
3 bd · 2 ba · 1,675 sqft
West Winter Haven
MLS ID #TB8530908, SIVEN PREMIER REAL ESTATE.
Listing provided by Stellar MLS
$232,400
3339 Queens Cove Loop
Winter Haven, FL 33880
3 bd · 2 ba · 1,158 sqft
Queens Cove Ph 02
MLS ID #O6386232, ENTERA REALTY LLC.
Listing provided by Stellar MLS
$289,900
996 Summer Glen Dr
Winter Haven, FL 33880
4 bd · 2 ba · 1,851 sqft
Coventry Cove Ph Il
MLS ID #O6412843, ENTERA REALTY LLC.
Listing provided by Stellar MLS
$250,000
1816 5th St Se
Winter Haven, FL 33880
3 bd · 2 ba · 1,352 sqft
Southeast Terrace
MLS ID #L4966255, KELLER WILLIAMS REALTY SMART 1.
Listing provided by Stellar MLS
$180,000
3349 Timberline Rd W
Winter Haven, FL 33880
2 bd · 2 ba · 994 sqft
Timber Wood
MLS ID #L4966253, KELLER WILLIAMS REALTY SMART 1.
Listing provided by Stellar MLS
$319,900
714 Avenue O Se
Winter Haven, FL 33880
5 bd · 2 ba · 2,104 sqft
Highland Estates
MLS ID #O6443591, HOUWZER INC.
Listing provided by Stellar MLS
$255,000
218 6th Jpv St
Winter Haven, FL 33880
3 bd · 2 ba · 1,228 sqft
Jan Phyl Village Rep
MLS ID #P4940098, BROKERS REALTY OF CENTRAL FLOR.
Listing provided by Stellar MLS
$155,000
2050 San Marcos Dr Se #211
Winter Haven, FL 33880
2 bd · 2 ba · 1,078 sqft
Park Lake 03 02 Amd
MLS ID #P4940172, BROKERS REALTY OF CENTRAL FLOR.
Listing provided by Stellar MLS
$349,900
4273 Stafford Dr
Winter Haven, FL 33880
3 bd · 2 ba · 1,475 sqft
Lake Thomas Woods Add 03
MLS ID #P4935622, THOMAS REALTY.
Listing provided by Stellar MLS
$418,000
4734 Monterey Dr
Winter Haven, FL 33880
4 bd · 3 ba · 2,687 sqft
MLS ID #L4964145, PROPERTY SHOPPE OF CENTRAL FL.
Listing provided by Stellar MLS
$50,000
138 1st Eloise St
Winter Haven, FL 33880
0.23 acres
Leslie J A Sub
MLS ID #R4911764, FREEDOM PROPERTY AGENT LLC.
Listing provided by Stellar MLS
$272,000
702 Avenue C Sw
Winter Haven, FL 33880
5 bd · 3 ba · 1,726 sqft
Sunset Park
MLS ID #O6442691, AGENT TRUST REALTY CORPORATION.
Listing provided by Stellar MLS
$279,000
212 Majestic Gardens Ln
Winter Haven, FL 33880
3 bd · 2 ba · 1,348 sqft
Gardens Ph 01
MLS ID #TB8547254, EXP REALTY LLC.
Listing provided by Stellar MLS
$118,000
4157 Rolling Oaks Dr
Winter Haven, FL 33880
2 bd · 2 ba · 1,464 sqft
Oakwood Estates
MLS ID #L4966053, LA ROSA REALTY PRESTIGE.
Listing provided by Stellar MLS
$349,900
906 Avenue M Se
Winter Haven, FL 33880
3 bd · 2 ba · 1,890 sqft
Lesnick Park
MLS ID #P4939351, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$315,000
292 Spirit Landings Cir
Winter Haven, FL 33880
4 bd · 3 ba · 2,332 sqft
Spirit Lndgs
MLS ID #O6305100, KELLER WILLIAMS ADVANTAGE III.
Listing provided by Stellar MLS
$249,000
151 1st St
Winter Haven, FL 33880
3 bd · 2 ba · 1,259 sqft
Leslie J A Sub
MLS ID #O6413676, MILLI REAL ESTATE SERVICES LLC.
Listing provided by Stellar MLS
$324,500
1508 Majestic Ln
Winter Haven, FL 33880
4 bd · 3 ba · 1,900 sqft
Eagle Lndg Ph Ii
MLS ID #L4962086, LA ROSA REALTY PRESTIGE.
Listing provided by Stellar MLS
$319,900
113 Avenue C Se
Winter Haven, FL 33880
4 bd · 2 ba · 1,392 sqft
Haven Terrace
MLS ID #O6443878, LPT REALTY, LLC.
Listing provided by Stellar MLS
$225,000
3344 Timberline Rd W
Winter Haven, FL 33880
2 bd · 2 ba · 904 sqft
Timber Wood
MLS ID #W7889482, KELLER WILLIAMS REALTY- PALM HARBOR.
Listing provided by Stellar MLS
$160,000
217 Grove Ridge Dr
Winter Haven, FL 33880
2 bd · 2 ba · 1,344 sqft
MLS ID #L4964035, LA ROSA REALTY PRESTIGE.
Listing provided by Stellar MLS
$195,000
1828 Avenue O Sw
Winter Haven, FL 33880
3 bd · 2 ba · 1,354 sqft
Orangewood Add
MLS ID #A4711107, FLATFEE.COM.
Listing provided by Stellar MLS
$294,999
265 Majestic Gardens Ln
Winter Haven, FL 33880
3 bd · 2 ba · 1,951 sqft
Gardens Ph 01
MLS ID #L4962565, BHHS FLORIDA PROPERTIES GROUP.
Listing provided by Stellar MLS
More Winter Haven Homes for Sale
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 5, 2026 at 5:45 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