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3 beds New construction With a pool

4 Bedroom Homes in Winter Haven, FL

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24 of 205 Listings

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24 of 205 Listings

Price Reduced33

4 Bedroom Homes in Winter Haven, FL — Page 4

205 listings

4 Bedroom Homes in Winter Haven, FL

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24 of 205 Listings

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4 Bedroom Homes in Winter Haven, FL

24 of 205 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced33

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$300,000

4 bd · 3 ba · 1,964 sqft

1166 Yumuri St, Winter Haven, FL

Francis Zipeto · KELLER WILLIAMS CLASSIC

31Active

$359,900

4 bd · 2 ba · 2,522 sqft

2145 River Hawk Loop, Winter Haven, FL

Rodrigo Gomes De Almeida · KELLER WILLIAMS REALTY SMART 1

Price Reduced53Active

$419,900

4 bd · 3 ba · 2,687 sqft

4734 Monterey Dr, Winter Haven, FL

Damon Trueman · PROPERTY SHOPPE OF CENTRAL FL

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

28Active

$329,900

4 bd · 2 ba · 2,020 sqft

312 Towhee Rd, Winter Haven, FL

Ike Fountain · FREEDOM REALTY

Price Reduced59Active

$314,000

4 bd · 3 ba · 2,200 sqft

1836 Carnostie Rd, Winter Haven, FL

Trisha Deokinandan · ALORA REALTY GROUP INC

13Active

$305,000

4 bd · 3 ba · 1,879 sqft

981 Harold Pass, Winter Haven, FL

Ashley Porto · GLASSTONE GROUP INC

38Active

$326,990

4 bd · 2 ba · 1,828 sqft

2759 Adeline Ave, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

28Active

$289,900

4 bd · 2 ba · 1,476 sqft

116 Harbor Dr, Winter Haven, FL

Allison McDaniel · XCELLENCE

33Active

$255,000

4 bd · 2 ba · 1,532 sqft

1024 31st St NW, Winter Haven, FL

Marco Silva Bravo · GOYAL & DECOSTER REALTY

Price Reduced25Active

$321,299

4 bd · 3 ba · 2,226 sqft

5386 San Pietro Dr, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

15Active

$299,000

4 bd · 2 ba · 1,833 sqft

7158 Summit Pl, Winter Haven, FL

Glenda Pruitt · FLORIDA HOME CHOICE REALTY

2Active

$399,990

4 bd · 3 ba · 2,061 sqft

819 Andrew St, Winter Haven, FL

Adam Schott · DRB GROUP REALTY, LLC

Price Reduced41Active

$219,900

4 bd · 3 ba · 1,936 sqft

3941 Warbler Dr, Winter Haven, FL

Mark D'Italia · PROPERTY LOGIC RE

Price Reduced32Active

$389,900

4 bd · 2 ba · 2,420 sqft

408 Coleman Dr, Winter Haven, FL

Michael Mcgee · MAINSTAY BROKERAGE LLC

14Active

$330,900

4 bd · 4 ba · 2,227 sqft

4498 Rapallo Ave E, Winter Haven, FL

George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

21Active

$350,165

4 bd · 2 ba · 2,021 sqft

2236 Labrador Loop, Winter Haven, FL

Bill Maltbie · MALTBIE REALTY GROUP

22Active

$395,470

4 bd · 3 ba · 2,797 sqft

2232 Labrador Loop, Winter Haven, FL

Bill Maltbie · MALTBIE REALTY GROUP

48Active

$470,000

4 bd · 2 ba · 1,990 sqft

4123 Island Lakes Dr, Winter Haven, FL

Michelle Howard · KELLER WILLIAMS REALTY SMART 1

35Active

$326,490

4 bd · 3 ba · 2,305 sqft

6064 Navona Way, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

48Active

$425,000

4 bd · 3 ba · 2,434 sqft

5009 Strada Dr, Winter Haven, FL

Florentino Beltran · KELLER WILLIAMS ADVANTAGE 2 REALTY

Price ReducedOpen house Sat, Oct 10 · 1:00 PM35Active

$289,990

4 bd · 2 ba · 1,625 sqft

296 Meredith Blvd, Winter Haven, FL

Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

Price Reduced40Active

$299,900

4 bd · 3 ba · 1,933 sqft

1325 Diego Ter, Winter Haven, FL

Maritza Saint Hilaire · OLYMPUS EXECUTIVE REALTY INC

15Active

$580,000

4 bd · 3 ba · 2,050 sqft

915 Hillside Ct S, Winter Haven, FL

Karen Myers · UNITED REALTY GROUP INC

37Active

$376,990

4 bd · 3 ba · 2,308 sqft

1734 Hummingbird Rd, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

1…3 4 5…9

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 99.7% of asking price

Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $270,000$207,500–$329,495 typical range
Price per sq. ft.: $161
Sales: 135
Paid in cash: 36.3%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 48 days

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

Year-over-year: -18.2%

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.

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

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New Construction Homes
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55+ Community Homes

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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 99.7% of asking price

Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $270,000$207,500–$329,495 typical range
Price per sq. ft.: $161
Sales: 135
Paid in cash: 36.3%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 48 days

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

Year-over-year: -18.2%

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.