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3 beds New construction With a pool

2 Bedroom Homes in Winter Haven, FL

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24 of 177 Listings

Map

24 of 177 Listings

31Active

2 Bedroom Homes in Winter Haven, FL — Page 4

177 listings

2 Bedroom Homes in Winter Haven, FL

Hide Map

24 of 177 Listings

Map

2 Bedroom Homes in Winter Haven, FL

24 of 177 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

31Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$150,000

2 bd · 2 ba · 1,008 sqft

489 Village Cir SW, Winter Haven, FL

Lindsey Funderburk · JT REALTY & ASSOCIATES

Price Reduced40Active

$160,000

2 bd · 2 ba · 1,017 sqft

1105 Eagle Pond Dr #1105, Winter Haven, FL

Kayly Malinas, PA · JOHN WOOD REALTY, INC.

42Active

$115,000

2 bd · 2 ba · 1,368 sqft

113 Lake Hazel Dr, Winter Haven, FL

Chris Cain · MOSAIC SERVICES LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced27Active

$205,000

2 bd · 1 ba · 900 sqft

434 Avenue D SE, Winter Haven, FL

Kellie Hicks · LOCKHART & ASSOCIATES INC

62Active

$110,000

2 bd · 2 ba · 1,104 sqft

4807 Plumwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

33Active

$129,500

2 bd · 1 ba · 826 sqft

1100 Martinique Dr #106, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

36Active

$165,000

2 bd · 2 ba · 1,139 sqft

665 Broadmoor Cir, Winter Haven, FL

Rayven Santiago · KELLER WILLIAMS REALTY Y

26Active

$185,000

2 bd · 1 ba · 934 sqft

790 Avenue Q SE, Winter Haven, FL

Amy Reynolds · LOCKHART & ASSOCIATES INC

51Active

$149,900

2 bd · 2 ba · 1,190 sqft

700 Mirror Ter NW #511, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced56Active

$92,000

2 bd · 1 ba · 840 sqft

1700 6th St NW #C24, Winter Haven, FL

Chrissi Jasso · ASSOCIATE REALTY

33Active

$78,800

2 bd · 1 ba · 840 sqft

1700 6th St NW #a38, Winter Haven, FL

Shelby Beasley · S & D REAL ESTATE SERVICE LLC

23Active

$215,000

2 bd · 2 ba · 952 sqft

5 Moonlight Ln, Winter Haven, FL

Alicia Davis · KELLER WILLIAMS REALTY SMART 1

Price Reduced18Active

$170,000

2 bd · 1 ba · 896 sqft

139 Avenue G SE, Winter Haven, FL

Paola Arias · MBA REALTY GROUP, INC

35Active

$162,000

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #807, Winter Haven, FL

Lisa Simpson · KELLER WILLIAMS REALTY SMART 1

34Active

$140,000

2 bd · 2 ba · 1,144 sqft

6666 Briarhill Dr NE, Winter Haven, FL

EJ Jimenez · KELLER WILLIAMS ADVANTAGE III

Price Reduced53Active

$155,000

2 bd · 2 ba · 1,080 sqft

6235 Knotty Pine Dr SE, Winter Haven, FL

Kelly Jones · KELLER WILLIAMS REALTY SMART 1

Price Reduced35Active

$219,000

2 bd · 1 ba · 1,199 sqft

1365 Sheridan St SW, Winter Haven, FL

Tina Ford · BERRY REALTY & APPRAISAL SERVICES PA

Price Reduced16Active

$220,000

2 bd · 1 ba · 1,137 sqft

1405 28th St NW, Winter Haven, FL

Matthew Hazlett · EXP REALTY LLC

Price Reduced18Active

$145,000

2 bd · 1 ba · 840 sqft

3319 Avenue U NW, Winter Haven, FL

Jason Braddock · EXP REALTY LLC

Price Reduced57Active

$110,000

2 bd · 2 ba · 1,056 sqft

4242 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced35Active

$199,000

2 bd · 2 ba · 1,333 sqft

1525 Oakview Cir SE, Winter Haven, FL

Rich Gant · LPT REALTY, LLC

18Active

$92,000

2 bd · 2 ba · 840 sqft

1700 6th St NW #C21, Winter Haven, FL

Don Jerue · KELLER WILLIAMS REALTY SMART 1

64Active

$140,000

2 bd · 2 ba · 1,344 sqft

4146 Sprucewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced33Active

$229,000

2 bd · 2 ba · 1,395 sqft

664 Clubhouse Rd, Winter Haven, FL

Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

1…3 4 5…8

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 99.9% 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 30, 2026

Median sale price: $270,000$195,000–$332,030 typical range
Price per sq. ft.: $159
Sales: 200
Paid in cash: 38.0%

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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Single-Family Homes
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By feature

New Construction Homes
Homes with a Pool
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Open Houses
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 99.9% 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 30, 2026

Median sale price: $270,000$195,000–$332,030 typical range
Price per sq. ft.: $159
Sales: 200
Paid in cash: 38.0%

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.