Homes Under $500K in Winter Haven, FL

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24 of 736 Listings

Map

24 of 736 Listings

New33

736 listings

Homes Under $500K in Winter Haven, FL

Show Map

24 of 736 Listings

Map

Homes Under $500K in Winter Haven, FL

24 of 736 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New33

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$279,990

4 bd · 2 ba · 1,851 sqft

3101 Royal Tern Dr, Winter Haven, FL

Paul Jacques · XCELLENCE

New43Active

$259,900

2 bd · 2 ba · 1,843 sqft

441 San Jose Dr, Winter Haven, FL

Brian Cox · KELLER WILLIAMS REALTY SMART 1

New4Active

$262,950

3 bd · 2 ba · 1,286 sqft

3883 Avenue O NW, Winter Haven, FL

Angie Reynolds · PORCHLIGHT HOMES LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New29Active

$245,000

4 bd · 2 ba · 1,683 sqft

720 Lake Ned Rd, Winter Haven, FL

Jeff Jones · MARK SPAIN REAL ESTATE

19Active

$175,000

2 bd · 2 ba · 1,103 sqft

1905 Garden Lake Dr, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

New72Active

$434,700

3 bd · 2 ba · 2,312 sqft

1321 Oakmont Dr, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

New23Active

$309,900

3 bd · 2 ba · 1,525 sqft

3304 Costello Cir, Winter Haven, FL

Jason Stone · BHHS FLORIDA PROPERTIES GROUP

New74Active

$179,000

3 bd · 3 ba · 1,584 sqft

5850 Cypress Gardens Blvd #303, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

Open house Sun, Oct 4 · 1:00 PM52Active

$249,000

2 bd · 3 ba · 1,380 sqft

950 14th St NE, Winter Haven, FL

Laura Slocumb · REMAX EXPERTS

30Active

$295,000

3 bd · 2 ba · 1,246 sqft

5814 Driftwood Dr, Winter Haven, FL

Solomon Gallant · S & D REAL ESTATE SERVICE LLC

New41Active

$330,000

3 bd · 2 ba · 1,959 sqft

645 Avenue M SE, Winter Haven, FL

Bryan Dicks · COLDWELL BANKER REALTY

New24Active

$200,000

3 bd · 2 ba · 1,345 sqft

651 Lake Dexter Cir, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

New38Active

$250,000

2 bd · 2 ba · 1,507 sqft

4302 Shadow Wood Ln, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

New27Active

$145,000

2 bd · 1 ba · 1,209 sqft

624 Lake Elizabeth Dr, Winter Haven, FL

Cheryl Kypreos · HOMESMART

13Active

$350,000

4 bd · 2 ba · 2,280 sqft

521 Adriel Ave, Winter Haven, FL

William Ortiz Collazo · LA ROSA REALTY KISSIMMEE

66Active

$335,000

3 bd · 2 ba · 2,148 sqft

1215 Fairlane Ct NW, Winter Haven, FL

Bree Allison · KELLER WILLIAMS TAMPA CENTRAL

NewOpen house Fri, Oct 2 · 4:00 PM51Active

$425,000

4 bd · 3 ba · 2,280 sqft

2900 Crump Rd, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

New27Active

$236,990

3 bd · 3 ba · 1,423 sqft

3039 Captain Jax Way, Winter Haven, FL

Ben Goldstein · LENNAR REALTY

New27Active

$236,990

3 bd · 3 ba · 1,423 sqft

3059 Captain Jax Way, Winter Haven, FL

Ben Goldstein · LENNAR REALTY

37Active

$336,990

5 bd · 3 ba · 2,447 sqft

6055 Navona Way, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

37Active

$360,000

5 bd · 3 ba · 2,616 sqft

4230 Roberta Dr, Winter Haven, FL

Giovanni Hernandez · FORTEX REALTY INC

35Active

$149,900

3 bd · 3 ba · 1,622 sqft

100 El Camino Dr #301, Winter Haven, FL

Craig Burke · CRAIG BURKE REAL ESTATE GROUP, LLC

52Active

$419,000

3 bd · 2 ba · 2,099 sqft

215 S Lake Howard Dr, Winter Haven, FL

Brandy Duncan · COLDWELL BANKER REALTY

33Active

$309,990

4 bd · 3 ba · 1,866 sqft

6059 Navona Way, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Haven housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400

Winter Haven, FL community profile

Population: 58,351
Median income: $56,564
Housing units: 26,800
People per sq. mi.: 605.3
Area: 96.4 sq. mi.

Source: HJN community data

Explore Winter Haven homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Haven, FL community profile

Population: 58,351
Median income: $56,564
Housing units: 26,800
People per sq. mi.: 605.3
Area: 96.4 sq. mi.

Source: HJN community data

Winter Haven housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400

Homes for sale

762

Median days on market

49 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,632 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Haven housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Winter Haven, FL community profile

Explore Winter Haven homes

Your local brokerage

Listing data & MLS disclosures

Winter Haven, FL community profile

Winter Haven housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026