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3 beds New construction With a pool

2 Bedroom Homes in Winter Haven, FL

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24 of 176 Listings

Map

24 of 176 Listings

2 Bedroom Homes in Winter Haven, FL — Page 3

176 listings

2 Bedroom Homes in Winter Haven, FL

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24 of 176 Listings

Map

2 Bedroom Homes in Winter Haven, FL

24 of 176 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$220,000

2 bd · 2 ba · 1,664 sqft

6600 Scenic Point Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

35Active

$179,000

2 bd · 2 ba · 1,248 sqft

6458 Hollyberry Ln NE, Winter Haven, FL

Harrison Perez Collazo · CAISSA REALTY INVESTMENT INC

34Active

$144,900

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #308, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced17Active

$215,000

2 bd · 2 ba · 1,134 sqft

119 Lantern Ln, Winter Haven, FL

Jeff Jones · MARK SPAIN REAL ESTATE

Price Reduced31Active

$159,000

2 bd · 2 ba · 1,017 sqft

508 Eagle Pond Dr #508, Winter Haven, FL

Laura Barnes · CHAIN OF LAKES REALTY INC

27Active

$147,500

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #504, Winter Haven, FL

Annette Bagwell · ELEVATED REALTY

11Active

$54,900

2 bd · 1 ba · 672 sqft

213 Lakeside Ranch Cir, Winter Haven, FL

Nadia Aguilar · EXIT REALTY 4CORNERS

Price Reduced37Active

$114,900

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #409, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

13Active

$103,000

2 bd · 2 ba · 1,260 sqft

86 Parson Dr, Winter Haven, FL

Darlene Bice · TOWN & COUNTRY REAL ESTATE

Price Reduced12Active

$65,000

2 bd · 2 ba · 864 sqft

187 Sweet Cir, Winter Haven, FL

Darlene Bice · TOWN & COUNTRY REAL ESTATE

46Active

$158,500

2 bd · 2 ba · 1,404 sqft

6703 Canterbury Dr NE, Winter Haven, FL

Brad Martin · BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

16Active

$135,000

2 bd · 2 ba · 1,073 sqft

242 Winter Ridge Blvd #242, Winter Haven, FL

Vikki Thielen · THE MARKET REALTY COMPANY

Price Reduced14Active

$189,900

2 bd · 1 ba · 840 sqft

1248 31st St NW, Winter Haven, FL

Ronnie Holloman · HOLLOMAN GORDON REALTY, INC.

Price Reduced30Active

$239,900

2 bd · 2 ba · 1,092 sqft

2608 Trinity Cir NW, Winter Haven, FL

Natalie Oldenkamp · BHHS FLORIDA PROPERTIES GROUP

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

Price Reduced57Active

$100,000

2 bd · 2 ba · 942 sqft

345 24th St NW #1, Winter Haven, FL

Ronnie DeCarlo · KELLER WILLIAMS CLASSIC

Price Reduced33Active

$209,000

2 bd · 2 ba · 1,090 sqft

410 Laurel Cove Way, Winter Haven, FL

Carlos Hernandez · LPT REALTY, LLC

Price Reduced66Active

$169,900

2 bd · 2 ba · 1,200 sqft

6086 Southern Oaks Dr, Winter Haven, FL

Joanne Summeralls · COLDWELL BANKER REALTY

Price Reduced64Active

$145,000

2 bd · 2 ba · 1,072 sqft

689 Lake Howard Dr NW #213, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

1Active

$99,900

2 bd · 2 ba · 840 sqft

1700 6th St NW #C31, Winter Haven, FL

Candace Garber · TRUDEALS REALTY CORP

43Active

$164,800

2 bd · 2 ba · 1,325 sqft

628 Lakeside Ranch Ln, Winter Haven, FL

Sanda Andrews · GOOD COMPANY REALTY INC.

76Active

$139,900

2 bd · 2 ba · 1,804 sqft

4234 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced58Active

$224,500

2 bd · 2 ba · 1,090 sqft

503 Sweet Bay Cir, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

31Active

$150,000

2 bd · 2 ba · 1,008 sqft

489 Village Cir SW, Winter Haven, FL

Lindsey Funderburk · JT REALTY & ASSOCIATES

1 2 3 4…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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2 Bedroom 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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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.