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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 Reduced42

2 Bedroom Homes in Winter Haven, FL — Page 6

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 Reduced42

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$159,900

2 bd · 2 ba · 1,288 sqft

6114 Grand Oaks Dr SE, Winter Haven, FL

Kimberly Davis · CROSBY & ASSOCIATES, INC.

Price Reduced48Active

$139,900

2 bd · 2 ba · 1,000 sqft

447 Village Cir SW, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

56Active

$195,000

2 bd · 2 ba · 1,008 sqft

4925 Cypress Gardens Rd #100, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

55Active

$146,000

2 bd · 2 ba · 1,107 sqft

6473 Peppertree Path NE, Winter Haven, FL

Don Cleveland, JR · COLDWELL BANKER REALTY

Price Reduced65Active

$115,000

2 bd · 2 ba · 1,200 sqft

4155 Sprucewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced54Active

$154,000

2 bd · 2 ba · 1,248 sqft

6309 Grove Pointe Dr SE, Winter Haven, FL

Sanda Andrews · GOOD COMPANY REALTY INC.

Price Reduced21Active

$170,000

2 bd · 3 ba · 1,184 sqft

2500 21st St NW #15, Winter Haven, FL

Adriana Sanchez · AROD PARTNERS REALTY

Price Reduced63Active

$139,900

2 bd · 2 ba · 1,056 sqft

6773 Brentwood Dr NE, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced28Active

$151,000

2 bd · 2 ba · 1,144 sqft

6450 Hollyberry Ln NE, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced23Active

$142,500

2 bd · 2 ba · 1,252 sqft

607 Country Ln NE #607, Winter Haven, FL

Glenda Pruitt · FLORIDA HOME CHOICE REALTY

Price Reduced18Active

$114,900

2 bd · 1 ba · 672 sqft

220 King Rd, Winter Haven, FL

Craig Burke · CRAIG BURKE REAL ESTATE GROUP, LLC

63Active

$125,000

2 bd · 2 ba · 1,008 sqft

4918 Rosewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced35Active

$179,000

2 bd · 1 ba · 1,080 sqft

121 Bates Ave SE, Winter Haven, FL

Emily Jones · RE/MAX REALTY PLUS

Price ReducedOpen house Sat, Oct 24 · 10:00 AM46Active

$245,000

2 bd · 2 ba · 1,158 sqft

1678 Linz Ct, Winter Haven, FL

Bryan Dicks · COLDWELL BANKER REALTY

25Active

$125,000

2 bd · 2 ba · 960 sqft

1700 6th St NW #B23, Winter Haven, FL

Jean Julme · CENTRIC REALTY SERVICES LLC

Price Reduced36Active

$299,999

2 bd · 3 ba · 1,408 sqft

503 Avenue B NW #503, Winter Haven, FL

James Barris · EXP REALTY LLC

31Active

$325,000

2 bd · 2 ba · 1,647 sqft

319 Niblick Cir, Winter Haven, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

Price Reduced35Active

$169,000

2 bd · 3 ba · 1,334 sqft

2500 21st St NW #23, Winter Haven, FL

Tomi Miller-Troupe · COLDWELL BANKER REALTY

Price Reduced32Active

$99,900

2 bd · 2 ba · 792 sqft

9705 Lake Bess Rd #715, Winter Haven, FL

Kathryn Valentine · THREE MOUNTAINS REALTY

Price Reduced39Active

$154,900

2 bd · 2 ba · 930 sqft

8304 Waterview Way #8304, Winter Haven, FL

Catrina Marshall · DALTON WADE INC

Price Reduced64Active

$125,000

2 bd · 2 ba · 1,368 sqft

4239 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced16Active

$210,000

2 bd · 2 ba · 1,220 sqft

1581 Oakview Cir SE, Winter Haven, FL

Vanessa Aybar Badillo · LPT REALTY, LLC

Price Reduced30Active

$390,000

2 bd · 2 ba · 1,538 sqft

194 S Lake Mariam Dr, Winter Haven, FL

Don Jerue · KELLER WILLIAMS REALTY SMART 1

Price Reduced70Active

$114,900

2 bd · 2 ba · 1,104 sqft

4056 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

1…5 6 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

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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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.