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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

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24 of 176 Listings

Price Reduced72

2 Bedroom Homes in Winter Haven, FL — Page 2

176 listings

2 Bedroom Homes in Winter Haven, FL

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24 of 176 Listings

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2 Bedroom Homes in Winter Haven, FL

24 of 176 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced72

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$254,000

2 bd · 2 ba · 1,277 sqft

400 Bayou Rd, Winter Haven, FL

Tina McDonald · OLYMPUS EXECUTIVE REALTY INC

21Active

$162,000

2 bd · 2 ba · 1,017 sqft

1205 Eagle Pond Dr #1205, Winter Haven, FL

Gabriel Silva Andrada · FLORIDA SPIRIT HOMES

Price Reduced53Active

$344,900

2 bd · 2 ba · 1,888 sqft

4075 Bedford Ave, Winter Haven, FL

Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

35Active

$169,900

2 bd · 2 ba · 768 sqft

5974 Foxhollow Dr, Winter Haven, FL

Nancy Rosa Cruz · TFP FLORIDA REALTY LLC

Price Reduced17Active

$145,998

2 bd · 1 ba · 826 sqft

213 10th Wahneta St W, Winter Haven, FL

Jennifer Daniell · J&T PROPERTY SOLUTIONS GROUP LLC

33Active

$210,000

2 bd · 2 ba · 1,224 sqft

2206 San Marcos Cir SE, Winter Haven, FL

Tomi Miller-Troupe · COLDWELL BANKER REALTY

25Active

$119,000

2 bd · 1 ba · 826 sqft

1100 Martinique Dr #203, Winter Haven, FL

Cyleste Goodson · FLORIDA REAL ESTATE COMPANY

Price Reduced38Active

$660,000

2 bd · 2 ba · 2,230 sqft

2425 Gerber Dairy Rd, Winter Haven, FL

Tracy Holmes · KELLER WILLIAMS REALTY SMART 1

32Active

$165,000

2 bd · 2 ba · 1,014 sqft

6204 Knotty Pine Dr SE, Winter Haven, FL

Susan Brown · COLDWELL BANKER REALTY

15Active

$129,900

2 bd · 2 ba · 823 sqft

606 Pavare Ct #606, Winter Haven, FL

Amy Reynolds · LOCKHART & ASSOCIATES INC

34Active

$79,500

2 bd · 2 ba · 989 sqft

97 Parson Dr, Winter Haven, FL

Chris Cain · MOSAIC SERVICES LLC

Price Reduced32Active

$225,000

2 bd · 2 ba · 904 sqft

3344 Timberline Rd W, Winter Haven, FL

Eric Jenkins, PA · KELLER WILLIAMS REALTY- PALM HARBOR

Price Reduced45Active

$245,000

2 bd · 2 ba · 1,666 sqft

2801 Wingfoot Ct, Winter Haven, FL

Nancy Cini · VILLAGE REALTY OF WINTER HAVEN

35Active

$215,000

2 bd · 2 ba · 1,143 sqft

6364 Lolly Bay Loop NE, Winter Haven, FL

Daniel Betancourt · EXP REALTY LLC

Price Reduced39Active

$92,900

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #304, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

27Active

$184,900

2 bd · 2 ba · 1,436 sqft

2215 Starboard Dr #29, Winter Haven, FL

Scott Kline · KLINE REAL ESTATE SERVICES

Price Reduced22Active

$145,000

2 bd · 2 ba · 1,073 sqft

350 Winter Ridge Blvd #350, Winter Haven, FL

Giovanna D'Alessandro · RP INVESTMENT REALTY LLC

41Active

$175,000

2 bd · 2 ba · 1,340 sqft

6107 Grand Oaks Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

Price Reduced12Active

$99,000

2 bd · 2 ba · 1,030 sqft

333 Lake Howard Dr NW #302B, Winter Haven, FL

Karen Myers · UNITED REALTY GROUP INC

25Active

$152,000

2 bd · 2 ba · 1,144 sqft

6455 Hollyberry Ln NE, Winter Haven, FL

Harrison Perez Collazo · CAISSA REALTY INVESTMENT INC

52Active

$198,000

2 bd · 2 ba · 1,856 sqft

6627 Westchester Dr NE, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

19Active

$139,000

2 bd · 2 ba · 1,148 sqft

1550 11th St NE #G6, Winter Haven, FL

Christopher Collany · COLLANY PROPERTIES

Price Reduced19Active

$230,000

2 bd · 2 ba · 1,240 sqft

625 Avenue B SW, Winter Haven, FL

Luis Lozano Padierna · REAL BROKER, LLC

40Active

$220,000

2 bd · 2 ba · 1,664 sqft

6600 Scenic Point Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

1 2 3…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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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.