5 Bedroom Homes in Winter Haven, FL

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11 Listings

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11 Listings

66Active

11 listings

5 Bedroom Homes in Winter Haven, FL

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11 Listings

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5 Bedroom Homes in Winter Haven, FL

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

66Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$725,000

5 bd · 3 ba · 2,916 sqft

9504 Waterford Oaks Blvd, Winter Haven, FL

Brooke Boyette · KELLER WILLIAMS TAMPA PROPERTIES

66Active

$750,000

5 bd · 4 ba · 3,611 sqft

9513 Waterford Oaks Blvd, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

44Active

$598,000

5 bd · 3 ba · 3,068 sqft

1020 Lena Run Ct, Winter Haven, FL

Sarah Garner · COLDWELL BANKER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced92Active

$750,000

5 bd · 4 ba · 3,694 sqft

1016 S Lake Mariam Dr, Winter Haven, FL

Kelly Jones · KELLER WILLIAMS REALTY SMART 1

52Active

$849,900

5 bd · 4 ba · 4,108 sqft

25 Lakewood Cswy, Winter Haven, FL

Melissa Meyer · KEENE'S POINTE REALTY

80Active

$765,000

5 bd · 4 ba · 3,812 sqft

328 Hamilton Shores Dr NE, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

Price Reduced57Active

$519,990

5 bd · 3 ba · 2,653 sqft

445 Talamone Dr, Winter Haven, FL

Jimmy Aguilar · 3D TEAM REALTY LLC

Price Reduced59Active

$430,000

5 bd · 3 ba · 2,577 sqft

3097 Buckeye Pointe Dr, Winter Haven, FL

Desiree Carlson · RE/MAX HERITAGE PROFESSIONALS

67Active

$1,195,000

5 bd · 6 ba · 3,235 sqft

250 Brigham Rd NW, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced15Active

$299,000

5 bd · 2 ba · 4,053 sqft

1450 W Lake Cannon Dr NW, Winter Haven, FL

Veronica Davis · EXP REALTY LLC

Price Reduced69Active

$479,000

5 bd · 3 ba · 2,006 sqft

1818 6th St SE, Winter Haven, FL

Washington Costa · GARCIA REALTY GROUP

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

August 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $280,000$204,200–$384,975 typical range
Price per sq. ft.: $154
Sales: 290
Paid in cash: 45.2%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 34 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -5.1%

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

August 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $280,000$204,200–$384,975 typical range
Price per sq. ft.: $154
Sales: 290
Paid in cash: 45.2%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 34 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -5.1%

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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 Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 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 Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026