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3 beds New construction With a pool

4 Bedroom Homes in Winter Haven, FL

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13 of 205 Listings

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13 of 205 Listings

Price Reduced25Active

4 Bedroom Homes in Winter Haven, FL — Page 9

205 listings

4 Bedroom Homes in Winter Haven, FL

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13 of 205 Listings

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4 Bedroom Homes in Winter Haven, FL

13 of 205 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced25Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$445,000

4 bd · 3 ba · 2,850 sqft

240 Santa Rosa Dr, Winter Haven, FL

Brian Surrency · LIVE FLORIDA REALTY

27Active

$288,900

4 bd · 2 ba · 1,665 sqft

4160 Giorgio Dr, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

Price Reduced52Active

$410,000

4 bd · 3 ba · 2,495 sqft

108 Lake Region Blvd N, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced50Active

$259,900

4 bd · 3 ba · 2,159 sqft

511 Marcia Loop, Winter Haven, FL

Deanna Stone · THE STONES REAL ESTATE FIRM

Price Reduced43Active

$287,500

4 bd · 2 ba · 1,836 sqft

1864 Emily Dr, Winter Haven, FL

Octavia Cheveresan · RE/MAX ACTION FIRST OF FLORIDA

Price ReducedOpen house Wed, Oct 7 · 12:00 PM21Active

$354,999

4 bd · 3 ba · 2,670 sqft

5331 Mickey Ave, Winter Haven, FL

Stephanie Morales, LLC · AXEN REALTY, LLC

Price Reduced13Active

$370,900

4 bd · 3 ba · 2,242 sqft

Address withheld · Winter Haven, FL

Erica Ranson · BROOKS REALTY GROUP LLC

Price Reduced54Active

$370,000

4 bd · 3 ba · 2,781 sqft

1908 Crossroads Blvd, Winter Haven, FL

Jill Lingenfelter · CENTURY 21 MYERS REALTY

1Active

$341,066

4 bd · 2 ba · 1,816 sqft

974 Lunar Ln, Winter Haven, FL

Ed Laderer · VANTAGE PROPERTY MANAGEMENT LLC

Price ReducedOpen house Sat, Oct 10 · 11:00 AM19Active

$339,999

4 bd · 3 ba · 2,077 sqft

5163 Kinsley Dr, Winter Haven, FL

Stephanie Morales, LLC · AXEN REALTY, LLC

Price Reduced15Active

$305,000

4 bd · 2 ba · 1,857 sqft

621 Vittorio Dr, Winter Haven, FL

Jesus Nessy · MY REALTY GROUP, LLC.

9Active

$219,000

4 bd · 2 ba · 1,520 sqft

119 Allen Ave, Winter Haven, FL

Randall Patrick · WESTBAY REAL ESTATE

Price ReducedOpen house Wed, Oct 7 · 12:00 PM17Active

$323,635

4 bd · 2 ba · 1,919 sqft

5147 Kinsley Dr, Winter Haven, FL

Stephanie Morales, LLC · AXEN REALTY, LLC

1…8 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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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.