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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

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24 of 177 Listings

Price Reduced38

2 Bedroom Homes in Winter Haven, FL — Page 5

177 listings

2 Bedroom Homes in Winter Haven, FL

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24 of 177 Listings

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2 Bedroom Homes in Winter Haven, FL

24 of 177 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced38

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$178,490

2 bd · 3 ba · 1,334 sqft

2500 21st St NW #22, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced23Active

$449,000

2 bd · 3 ba · 965 sqft

1620 17th St NW, Winter Haven, FL

Kimberly Saddler · LA ROSA REALTY PRESTIGE

31Active

$200,999

2 bd · 1 ba · 968 sqft

1101 28th St NW, Winter Haven, FL

Yulimar Machado · OUTLET REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced25Active

$199,000

2 bd · 2 ba · 1,090 sqft

105 Laurel Cove Way #105, Winter Haven, FL

Chip Fortenberry, III · CROSBY & ASSOCIATES, INC.

40Active

$119,000

2 bd · 2 ba · 1,190 sqft

700 Mirror Ter NW #506, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

28Active

$400,000

2 bd · 2 ba · 1,120 sqft

1549 Drexel Ave NE, Winter Haven, FL

Michael Brenner · CENTURY 21 MYERS REALTY

Price Reduced74Active

$119,900

2 bd · 2 ba · 1,403 sqft

4158 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced67Active

$124,000

2 bd · 2 ba · 1,344 sqft

4132 Sprucewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

38Active

$94,999

2 bd · 2 ba · 989 sqft

6443 Hollyberry Ln NE, Winter Haven, FL

Steve Donahue · LIVE FLORIDA REALTY

Price Reduced38Active

$290,000

2 bd · 2 ba · 1,260 sqft

132 Duval Rd, Winter Haven, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

40Active

$164,900

2 bd · 2 ba · 1,351 sqft

700 Mirror Ter NW #507, Winter Haven, FL

Scott Kline · KLINE REAL ESTATE SERVICES

61Active

$309,900

2 bd · 2 ba · 1,819 sqft

4130 Bedford Ave, Winter Haven, FL

Bryan Dicks · COLDWELL BANKER REALTY

Price Reduced36Active

$94,900

2 bd · 2 ba · 1,372 sqft

150 El Dorado #105, Winter Haven, FL

Rosalia Abreu · ALLSTATE REALTY SERVICES

25Active

$495,000

2 bd · 3 ba · 1,640 sqft

154 2nd Street SW #Unit 7, Winter Haven, FL

Zachary Strang · POLK REALTY ADVISORS LLC

Price Reduced44Active

$405,000

2 bd · 2 ba · 2,249 sqft

75 Sunset View Dr #75, Winter Haven, FL

Jill Lingenfelter · CENTURY 21 MYERS REALTY

22Active

$169,500

2 bd · 2 ba · 1,252 sqft

702 Country Ln NE #702, Winter Haven, FL

Glenda Pruitt · FLORIDA HOME CHOICE REALTY

Price Reduced37Active

$214,900

2 bd · 2 ba · 1,368 sqft

10 Enclave Dr, Winter Haven, FL

Erin Floyd · COLDWELL BANKER REALTY

Price Reduced52Active

$165,000

2 bd · 2 ba · 1,278 sqft

1004 Medinah Dr, Winter Haven, FL

Susan Human · HUMAN TOUCH REAL ESTATE FIRM

40Active

$235,000

2 bd · 2 ba · 1,385 sqft

3023 Caneel St, Winter Haven, FL

Marco Silva Bravo · GOYAL & DECOSTER REALTY

Price Reduced43Active

$129,900

2 bd · 2 ba · 1,265 sqft

4212 Cedarwood St, Winter Haven, FL

Karl Erickson · FLORIDA HOMES REALTY & MORTGAGE

Price Reduced33Active

$422,999

2 bd · 2 ba · 1,533 sqft

1108 Sawgrass Dr, Winter Haven, FL

Samuel Williams · LA ROSA REALTY CENTRAL FLORIDA LLC

Price Reduced70Active

$97,000

2 bd · 2 ba · 1,056 sqft

4253 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

38Active

$524,900

2 bd · 2 ba · 896 sqft

612 Morgan Rd, Winter Haven, FL

Stephanie Bombinski · AGENT GROUP REALTY

Price Reduced29Active

$189,000

2 bd · 2 ba · 972 sqft

1213 8th St NW, Winter Haven, FL

Holly Patterson · KELLER WILLIAMS REALTY SMART

1…4 5 6…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
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.

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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New Construction Homes
Homes with a Pool
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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.