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90 listings

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3 beds New construction With a pool

Homes with a Pool in Winter Haven, FL

90 listings

Homes with a Pool in Winter Haven, FL

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24 of 90 Listings

Map

Homes with a Pool in Winter Haven, FL

24 of 90 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New87

Active

$1,295,000

3 bd · 3 ba · 2,375 sqft

1921 Manor Cir SE, Winter Haven, FL

Dee Norris · NEXTHOME NORRIS & COMPANY REAL

New25Active

$515,000

5 bd · 3 ba · 2,685 sqft

2022 Kapree Ct, Winter Haven, FL

Jerome Baker · BAKER REAL ESTATE PRO. GR LLC

New31Active

$428,000

5 bd · 3 ba · 2,549 sqft

219 Terranova Blvd, Winter Haven, FL

Dwight Head · ALLSTATE REALTY SERVICES

New65Active

$559,900

4 bd · 3 ba · 2,775 sqft

7380 Bent Grass Dr, Winter Haven, FL

Twanna Dewdney · LA ROSA REALTY PRESTIGE

New54Active

$625,000

5 bd · 3 ba · 3,016 sqft

669 Sarner Pass Way, Winter Haven, FL

Miguel Shellie · MARK SPAIN REAL ESTATE

Open house Sat, Oct 17 · 4:30 PM35Active

$275,000

3 bd · 3 ba · 2,631 sqft

4253 Stafford Dr, Winter Haven, FL

Daniel Rodriguez · NEW HEIGHTS REALTY GROUP

51Active

$480,000

4 bd · 3 ba · 1,985 sqft

1075 8th St NW, Winter Haven, FL

Jim Knetsch · LPT REALTY, LLC

25Active

$255,000

3 bd · 2 ba · 1,228 sqft

218 6th Jpv St, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

33Active

$359,900

5 bd · 2 ba · 2,104 sqft

714 Avenue O SE, Winter Haven, FL

Ileana Perez · HOUWZER INC

21Active

$200,000

2 bd · 2 ba · 1,776 sqft

104 13th St SE, Winter Haven, FL

Chuck Ferdinandsen · CHARLES RUTENBERG REALTY ORLANDO

36Active

$485,000

4 bd · 2 ba · 2,400 sqft

10 W Lake Hamilton Cir, Winter Haven, FL

John Keller, III · JACK KELLER INC

57Active

$369,900

4 bd · 3 ba · 2,836 sqft

5809 Windridge Dr, Winter Haven, FL

Kimberly Davis · CROSBY & ASSOCIATES, INC.

61Active

$1,750,000

4 bd · 4 ba · 3,476 sqft

13 Bogey Dr, Winter Haven, FL

Cathy Kluytenaar · THE K TEAM REAL ESTATE SERVICES LLC

38Active

$515,000

3 bd · 2 ba · 2,638 sqft

37 Lake Eloise Ln, Winter Haven, FL

Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

30Active

$595,000

4 bd · 4 ba · 4,128 sqft

815 Lake Jessie Dr, Winter Haven, FL

Aline Oliveira · META ONE REALTY GROUP LLC

51Active

$224,900

3 bd · 1 ba · 1,733 sqft

1325 Lake Shipp Dr N, Winter Haven, FL

Denise Jones · CENTURY 21 MYERS REALTY

Open house Sat, Oct 17 · 11:00 AM51Active

$350,000

3 bd · 2 ba · 1,762 sqft

117 Homewood Dr, Winter Haven, FL

Lisa Matheny · ENGEL & VOELKERS LAKELAND

25Active

$340,000

3 bd · 2 ba · 1,888 sqft

7002 Summit Cir, Winter Haven, FL

Angela Fowler · ANGELA FOWLER REAL ESTATE, LLC

66Active

$725,000

5 bd · 3 ba · 2,916 sqft

9504 Waterford Oaks Blvd, Winter Haven, FL

Brooke Boyette · KELLER WILLIAMS TAMPA PROPERTIES

51Active

$419,000

3 bd · 3 ba · 2,613 sqft

119 Sunfish Dr, Winter Haven, FL

Carlos DeJesus · EXIT REALTY 4CORNERS

20Active

$430,000

4 bd · 2 ba · 2,489 sqft

9 Winterset Dr, Winter Haven, FL

Jennifer Perez Mojica · LPT REALTY, LLC

65Active

$750,000

5 bd · 4 ba · 3,611 sqft

9513 Waterford Oaks Blvd, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced32Active

$1,100,000

3 bd · 2 ba · 2,129 sqft

4401 Chambliss Rd, Winter Haven, FL

Cyleste Goodson · FLORIDA REAL ESTATE COMPANY

62Active

$765,000

3 bd · 2 ba · 2,678 sqft

3831 Gaines Dr, Winter Haven, FL

Jared Lippelgoos · COLDWELL BANKER REALTY

1 2…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.

About Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL: 90 active listings as of October 14, 2026, 20:53 UTC.

Winter Haven housing market

September 2026 · This period is still settling

Selling at 99.9% of asking price

Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 28, 2026

Median sale price: $270,000$196,000–$334,500 typical range
Price per sq. ft.: $160
Sales: 175
Paid in cash: 37.7%

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

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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

Condos

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By feature

New Construction Homes
Homes with a Pool
Waterfront Homes
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55+ Community Homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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 99.9% of asking price

Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 28, 2026

Median sale price: $270,000$196,000–$334,500 typical range
Price per sq. ft.: $160
Sales: 175
Paid in cash: 37.7%

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

42 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.

Homes with a Pool in Winter Haven, FL