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3 beds New construction With a pool

2 Bedroom Homes in Winter Haven, FL

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8 of 176 Listings

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8 of 176 Listings

1Active
$120,000
2 bd · 2 ba · 1,176 sqft

2 Bedroom Homes in Winter Haven, FL — Page 8

176 listings

2 Bedroom Homes in Winter Haven, FL

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8 of 176 Listings

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2 Bedroom Homes in Winter Haven, FL

8 of 176 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

1Active
$120,000
2 bd · 2 ba · 1,176 sqft

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

100 Lakeside Ranch Dr, Winter Haven, FL

Chanmarlie Lim · HOME WISE REALTY GROUP, INC.

Price Reduced31Active

$179,999

2 bd · 2 ba · 1,252 sqft

2218 Abbey Rd, Winter Haven, FL

Larry King · VIVA ORLANDO REALTY INC.

Price Reduced16Active

$205,000

2 bd · 2 ba · 1,118 sqft

1224 Vienna Square Dr, Winter Haven, FL

Don Jerue · KELLER WILLIAMS REALTY SMART 1

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced10Active

$124,000

2 bd · 2 ba · 1,050 sqft

689 Lake Howard Dr NW #1E, Winter Haven, FL

Maria Rivera · RIVERA & ASSOCIATES REALTY

Price Reduced46Active

$193,000

2 bd · 2 ba · 1,139 sqft

683 Broadmoor Cir #683, Winter Haven, FL

Darlene Bice · TOWN & COUNTRY REAL ESTATE

Price Reduced26Active

$248,000

2 bd · 2 ba · 1,164 sqft

1703 Linz Ct, Winter Haven, FL

Austin Schreiber · DGCF REALTY ADVISORS LLC

Price Reduced24Active

$79,000

2 bd · 2 ba · 1,128 sqft

508 Lakeside Ranch Way, Winter Haven, FL

Jean Murphy · CENTURY 21 MYERS REALTY

Price Reduced34Active

$139,000

2 bd · 2 ba · 1,332 sqft

5850 Cypress Gardens Blvd #304, Winter Haven, FL

Matthew Davis · FLORIDA HOMES REALTY & MTG

1…7 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

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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.