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Homes with a Pool in Winter Haven, FL

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24 of 86 Listings

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24 of 86 Listings

Price Reduced58

Homes with a Pool in Winter Haven, FL — Page 2

86 listings

Homes with a Pool in Winter Haven, FL

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24 of 86 Listings

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Homes with a Pool in Winter Haven, FL

24 of 86 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced58

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$533,000

4 bd · 2 ba · 2,806 sqft

318 Hamilton Shores Dr NE, Winter Haven, FL

Dani Borow · KELLER WILLIAMS REALTY

Price Reduced25Active

$304,900

4 bd · 2 ba · 2,355 sqft

215 Santa Rosa Dr, Winter Haven, FL

Cynthia Fernandez · XCLUSIVE HOMES LLC

52Active

$849,900

5 bd · 4 ba · 4,108 sqft

25 Lakewood Cswy, Winter Haven, FL

Melissa Meyer · KEENE'S POINTE REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

63Active

$1,399,900

4 bd · 3 ba · 3,309 sqft

3640 Crump Rd, Winter Haven, FL

Amy Reynolds · LOCKHART & ASSOCIATES INC

48Active

$269,000

3 bd · 2 ba · 1,144 sqft

153 Browning Cir, Winter Haven, FL

Kimberly Jones · RE/MAX HERITAGE PROFESSIONALS

Price Reduced59Active

$789,900

4 bd · 3 ba · 3,648 sqft

9469 Waterford Oaks Dr, Winter Haven, FL

Zach Zehnder · KELLER WILLIAMS ST PETE REALTY

30Active

$330,000

4 bd · 3 ba · 2,836 sqft

5888 Windridge Dr, Winter Haven, FL

Danique Haywood · MARK SPAIN REAL ESTATE

Price Reduced26Active

$309,900

4 bd · 3 ba · 2,004 sqft

506 Clayton Cir, Winter Haven, FL

Anne Halbert · LIVE FLORIDA REALTY

Price Reduced44Active

$415,000

3 bd · 2 ba · 2,251 sqft

280 Santa Rosa Dr, Winter Haven, FL

Ashley James · KELLER WILLIAMS REALTY SMART 1

Price Reduced56Active

$880,000

2 bd · 3 ba · 2,768 sqft

1019 W Lake Eloise Ter, Winter Haven, FL

Ashley Adams · HOGAN & ASSOCIATES REAL ESTATE FIRM

17Active

$369,900

4 bd · 3 ba · 2,070 sqft

3035 Buckeye Pointe Dr, Winter Haven, FL

Wil Sanders · EXP REALTY LLC

Price Reduced50Active

$435,000

3 bd · 3 ba · 2,352 sqft

205 Thomas Ct, Winter Haven, FL

Stephanie Mayo · REGAL REAL ESTATE LLC

28Active

$289,900

4 bd · 2 ba · 1,476 sqft

116 Harbor Dr, Winter Haven, FL

Allison McDaniel · XCELLENCE

Price Reduced64Active

$389,000

3 bd · 4 ba · 1,675 sqft

228 W Lake Ina Dr, Winter Haven, FL

Casandra Vann · KELLER WILLIAMS REALTY

Price Reduced55Active

$264,900

3 bd · 2 ba · 1,172 sqft

1557 N Lake Shipp Dr SW, Winter Haven, FL

Tiffani Kline · HOUSE OF GLASS REAL ESTATE PM

Price Reduced32Active

$389,900

4 bd · 2 ba · 2,420 sqft

408 Coleman Dr, Winter Haven, FL

Michael Mcgee · MAINSTAY BROKERAGE LLC

100Active

$749,000

3 bd · 4 ba · 2,493 sqft

4040 Palma Ceia Cir, Winter Haven, FL

Deanna Stone · THE STONES REAL ESTATE FIRM

48Active

$425,000

4 bd · 3 ba · 2,434 sqft

5009 Strada Dr, Winter Haven, FL

Florentino Beltran · KELLER WILLIAMS ADVANTAGE 2 REALTY

Price Reduced37Active

$299,000

3 bd · 2 ba · 1,847 sqft

144 Waterside Cir, Winter Haven, FL

Ythamarie Rosario · KELLER WILLIAMS ADVANTAGE III

42Active

$435,000

3 bd · 2 ba · 2,702 sqft

1755 Beth Ln, Winter Haven, FL

Joni Reiter · COLDWELL BANKER REALTY

Price Reduced45Active

$249,765

3 bd · 2 ba · 1,473 sqft

3334 Avenue J NW, Winter Haven, FL

Nicki Salas Fuentes · ELEVE REAL ESTATE LLC

Price Reduced35Active

$349,900

3 bd · 2 ba · 1,890 sqft

906 Avenue M SE, Winter Haven, FL

Joleigh Nolen · COLDWELL BANKER REALTY

55Active

$125,000

1 bd · 1 ba · 714 sqft

235 6th St NW #307, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

Price Reduced69Active

$399,000

3 bd · 2 ba · 2,418 sqft

6704 Winterset Gardens Rd, Winter Haven, FL

Rachel Santos · WEICHERT REALTORS HALLMARK PRO

1 2 3 4

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

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

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%