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Buy

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

204 listings

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3 beds New construction With a pool

4 Bedroom Homes in Winter Haven, FL

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24 of 204 Listings

Map

24 of 204 Listings

33Active

4 Bedroom Homes in Winter Haven, FL — Page 5

204 listings

4 Bedroom Homes in Winter Haven, FL

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24 of 204 Listings

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4 Bedroom Homes in Winter Haven, FL

24 of 204 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

33Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$224,500

4 bd · 2 ba · 1,784 sqft

1500 Avenue H NE, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced44Active

$675,000

4 bd · 3 ba · 2,312 sqft

2004 Leisure Dr, Winter Haven, FL

Ralph Harvey · LISTWITHFREEDOM.COM

Price Reduced16Active

$237,500

4 bd · 2 ba · 1,828 sqft

1973 Carnostie Rd, Winter Haven, FL

Casandra Vann · KELLER WILLIAMS REALTY Y

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced40Active

$424,900

4 bd · 3 ba · 2,565 sqft

1714 Upland Ln, Winter Haven, FL

Daniel Araque · KELLER WILLIAMS LEGACY REALTY

60Active

$399,900

4 bd · 3 ba · 1,894 sqft

4132 Martindale Loop, Winter Haven, FL

Mike Webb · TRADE WINDS REALTY

Price Reduced83Active

$484,900

4 bd · 3 ba · 2,552 sqft

3158 Beauchamp Ct, Winter Haven, FL

Kennedy Matthews · JULIE MATTHEWS GROUP LLC

Price Reduced16Active

$279,900

4 bd · 3 ba · 3,016 sqft

709 Sarner Pass Way, Winter Haven, FL

Jesse Carriedo · REALTYCITY INC

Price Reduced40Active

$199,900

4 bd · 2 ba · 1,048 sqft

2390 29th St NW, Winter Haven, FL

John Scalia · EXP REALTY LLC

20Active

$314,900

4 bd · 2 ba · 1,863 sqft

1802 White Elephant Loop, Winter Haven, FL

Chris Courtney · PREFERRED REAL ESTATE BROKERS

Price Reduced15Active

$179,000

4 bd · 2 ba · 1,464 sqft

444 Avenue B NE, Winter Haven, FL

Malak Hassani Benbachir · KELLER WILLIAMS REALTY SMART 1

Price Reduced62Active

$299,000

4 bd · 2 ba · 1,907 sqft

372 Lake Daisy Cir, Winter Haven, FL

Chrissi Jasso · ASSOCIATE REALTY

Price Reduced79Active

$520,000

4 bd · 4 ba · 2,118 sqft

1475 S Lake Howard Dr, Winter Haven, FL

Deanna Stone · THE STONES REAL ESTATE FIRM

Price Reduced33Active

$260,000

4 bd · 2 ba · 1,840 sqft

428 McKenna Dr, Winter Haven, FL

EJ Jimenez · KELLER WILLIAMS ADVANTAGE III

Price Reduced41Active

$400,000

4 bd · 3 ba · 2,112 sqft

1826 6th St SE, Winter Haven, FL

Daphne Manning · LA ROSA REALTY PRESTIGE

Price Reduced28Active

$307,499

4 bd · 3 ba · 2,039 sqft

5449 San Pietro Dr, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

Price Reduced28Active

$309,380

4 bd · 3 ba · 2,039 sqft

5394 San Pietro Dr, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

Price Reduced86Active

$462,000

4 bd · 3 ba · 2,550 sqft

1814 Sandhill Ln, Winter Haven, FL

Stacy Tuttle · REMAX EXPERTS

Price Reduced30Active

$316,380

4 bd · 3 ba · 2,039 sqft

5445 San Pietro Dr, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

5Active

$329,900

4 bd · 3 ba · 1,896 sqft

1642 Teagan Ln, Winter Haven, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

Price Reduced65Active

$574,900

4 bd · 3 ba · 2,916 sqft

1801 Sandhill Ln, Winter Haven, FL

Emily Cassidy · LAND SOURCE REALTY, LLC

29Active

$318,000

4 bd · 2 ba · 1,654 sqft

5148 Magnolia Preserve Blvd, Winter Haven, FL

Teneke Outing · LA ROSA REALTY CENTRAL FLORIDA LLC

Price Reduced39Active

$649,900

4 bd · 3 ba · 3,155 sqft

815 Lake Ned Rd, Winter Haven, FL

Barry Macchione · REMAX EXPERTS

Price Reduced55Active

$385,000

4 bd · 3 ba · 2,356 sqft

136 Lake Mariam Rd SE, Winter Haven, FL

Jill Baird, LLC · KELLER WILLIAMS ADVANTAGE III

34Active

$339,900

4 bd · 2 ba · 1,720 sqft

1738 Hummingbird Rd, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

1…4 5 6…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

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

By price

Homes Under $100K
Homes Under $200K
Homes Under $300K
Homes Under $400K

By bedrooms

2 Bedroom Homes
3 Bedroom Homes
4 Bedroom Homes
5 Bedroom Homes

By type

Single-Family Homes
Townhomes
Condos
Manufactured Homes

By feature

New Construction Homes
Homes with a Pool
Waterfront Homes
Foreclosures & Short Sales
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.