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3 beds New construction With a pool

55+ Community Homes in Winter Haven, FL

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24 of 125 Listings

Map

24 of 125 Listings

Price Reduced33

55+ Community Homes in Winter Haven, FL — Page 4

125 listings

55+ Community Homes in Winter Haven, FL

Hide Map

24 of 125 Listings

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55+ Community Homes in Winter Haven, FL

24 of 125 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced33

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$422,999

2 bd · 2 ba · 1,533 sqft

1108 Sawgrass Dr, Winter Haven, FL

Samuel Williams · LA ROSA REALTY CENTRAL FLORIDA LLC

70Active

$99,000

2 bd · 2 ba · 1,056 sqft

4253 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced29Active

$189,000

2 bd · 2 ba · 972 sqft

1213 8th St NW, Winter Haven, FL

Holly Patterson · KELLER WILLIAMS REALTY SMART

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced42Active

$159,900

2 bd · 2 ba · 1,288 sqft

6114 Grand Oaks Dr SE, Winter Haven, FL

Kimberly Davis · CROSBY & ASSOCIATES, INC.

68Active

$395,000

4 bd · 3 ba · 2,322 sqft

3890 Bedford Ave, Winter Haven, FL

Christie Weeks · DREAM REALTY GROUP

48Active

$145,000

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

55Active

$146,000

2 bd · 2 ba · 1,107 sqft

6473 Peppertree Path NE, Winter Haven, FL

Don Cleveland, JR · COLDWELL BANKER REALTY

Price Reduced59Active

$95,000

2 bd · 2 ba · 720 sqft

4173 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Open house Sat, Oct 17 · 10:00 AM75Active

$579,900

3 bd · 2 ba · 2,354 sqft

5268 Pebble Beach Blvd, Winter Haven, FL

Barb Wiechmann · ROOST REALTY GROUP LLC

Price Reduced65Active

$115,000

2 bd · 2 ba · 1,200 sqft

4155 Sprucewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER 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 Reduced29Active

$100,000

2 bd · 2 ba · 1,056 sqft

125 Lake Hazel Dr, Winter Haven, FL

Jenn Manzella · FLORIDA REALTY MARKETPLACE

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

63Active

$125,000

2 bd · 2 ba · 1,008 sqft

4918 Rosewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced46Active

$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 Reduced26Active

$405,900

4 bd · 3 ba · 2,282 sqft

4020 Carteret Dr, Winter Haven, FL

Sofia Lovinsky · KELLER WILLIAMS ADVANTAGE III

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 Reduced70Active

$114,900

2 bd · 2 ba · 1,104 sqft

4056 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced42Active

$220,000

2 bd · 2 ba · 1,790 sqft

6825 S Lake Henry Dr NE, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

38Active

$169,500

2 bd · 2 ba · 1,080 sqft

6081 Southern Oaks Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

Price Reduced37Active

$120,000

2 bd · 2 ba · 1,008 sqft

345 24th St NW #25, Winter Haven, FL

Michele Elchin · DALTON WADE INC

1…3 4 5 6

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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 49 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.9%

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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 49 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.9%

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.