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3 beds New construction With a pool

55+ Community Homes in Winter Haven, FL

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24 of 126 Listings

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24 of 126 Listings

Price Reduced37

55+ Community Homes in Winter Haven, FL — Page 5

126 listings

55+ Community Homes in Winter Haven, FL

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24 of 126 Listings

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55+ Community Homes in Winter Haven, FL

24 of 126 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced37

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$120,000

2 bd · 2 ba · 1,008 sqft

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

Michele Elchin · DALTON WADE INC

62Active

$118,000

2 bd · 2 ba · 1,104 sqft

4228 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced38Active

$90,500

2 bd · 2 ba · 1,176 sqft

188 Sweet Circle Dr, Winter Haven, FL

Chris Cain · MOSAIC SERVICES LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced33Active

$96,000

3 bd · 3 ba · 1,666 sqft

400 El Camino Dr #210, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

35Active

$109,900

2 bd · 2 ba · 840 sqft

1700 6th St NW #C1, Winter Haven, FL

Annie Wood · HARPER REALTY FL, LLC

Price Reduced35Active

$279,975

3 bd · 2 ba · 1,725 sqft

257 Meadowbrook Blvd, Winter Haven, FL

Katherine Montana - De Jesus · KELLER WILLIAMS REALTY SMART 1

Price Reduced43Active

$444,000

3 bd · 2 ba · 2,045 sqft

6308 Pinehurst Loop, Winter Haven, FL

Cliff Glansen · FLATFEE.COM

Price Reduced15Active

$105,000

2 bd · 2 ba · 960 sqft

1700 6th St NW #B24, Winter Haven, FL

Rosa Suarez · LPT REALTY, LLC

Price Reduced21Active

$57,900

2 bd · 1 ba · 248 sqft

7041 Fairview Village Cir, Winter Haven, FL

Sandra Perry · WATSON REALTY CORP.

Price Reduced16Active

$65,000

1 bd · 1 ba · 931 sqft

100 El Camino Dr #111, Winter Haven, FL

Sharon Gastelbondo · LPT REALTY, LLC

Price Reduced68Active

$334,800

3 bd · 2 ba · 1,918 sqft

4577 Back Nine Dr, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

Price Reduced62Active

$284,500

3 bd · 2 ba · 2,109 sqft

2925 Dayton Dr, Winter Haven, FL

Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

Price Reduced54Active

$335,000

2 bd · 2 ba · 1,677 sqft

5197 Pebble Beach Blvd, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

Price Reduced19Active

$84,900

2 bd · 2 ba · 1,152 sqft

4165 Rolling Oaks Dr, Winter Haven, FL

Reta Stead · SOUTHERN BELLE REALTY

Price Reduced64Active

$106,000

2 bd · 2 ba · 1,216 sqft

4251 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced46Active

$158,000

2 bd · 2 ba · 1,248 sqft

6315 Grove Pointe Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

Price Reduced31Active

$104,900

2 bd · 2 ba · 1,056 sqft

4179 Rolling Oaks Dr, Winter Haven, FL

Reta Stead · SOUTHERN BELLE REALTY

Price Reduced11Active

$59,900

1 bd · 1 ba · 850 sqft

400 El Camino Dr #223, Winter Haven, FL

Scott Cohara · KELLER WILLIAMS CLASSIC

Price Reduced32Active

$129,900

2 bd · 2 ba · 1,120 sqft

6033 Grand Oaks Dr SE, Winter Haven, FL

Peggy Lewellen · COLDWELL BANKER REALTY

Price Reduced71Active

$248,000

2 bd · 2 ba · 1,164 sqft

1709 Linz Ct, Winter Haven, FL

Marti Sutton · CENTURY 21 WATSON & MYERS REALTY

Price Reduced41Active

$253,900

3 bd · 2 ba · 1,719 sqft

3923 Baldwin Ln, Winter Haven, FL

Brian Reeves · LPT REALTY, LLC

Price Reduced32Active

$75,000

3 bd · 2 ba · 1,176 sqft

95 Parson Dr, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

Price Reduced27Active

$99,000

2 bd · 2 ba · 1,008 sqft

4246 Cedarwood St, Winter Haven, FL

Andi Gamble · LPT REALTY, LLC

Price Reduced51Active

$145,000

2 bd · 2 ba · 1,248 sqft

6044 Grand Oaks Dr SE, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

1…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 99.7% of asking price

Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $270,000$207,500–$329,495 typical range
Price per sq. ft.: $161
Sales: 135
Paid in cash: 36.3%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $294,400

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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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 99.7% of asking price

Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $270,000$207,500–$329,495 typical range
Price per sq. ft.: $161
Sales: 135
Paid in cash: 36.3%

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

48 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.