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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

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24 of 125 Listings

33Active

55+ Community Homes in Winter Haven, FL — Page 3

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

33Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$78,800

2 bd · 1 ba · 840 sqft

1700 6th St NW #a38, Winter Haven, FL

Shelby Beasley · S & D REAL ESTATE SERVICE LLC

35Active

$162,000

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #807, Winter Haven, FL

Lisa Simpson · KELLER WILLIAMS REALTY SMART 1

29Active

$149,900

3 bd · 2 ba · 1,218 sqft

333 Lake Howard Dr NW #211B, Winter Haven, FL

Steven Smith, PA · LOCKHART & ASSOCIATES INC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

34Active

$140,000

2 bd · 2 ba · 1,144 sqft

6666 Briarhill Dr NE, Winter Haven, FL

EJ Jimenez · KELLER WILLIAMS ADVANTAGE III

Price Reduced53Active

$155,000

2 bd · 2 ba · 1,080 sqft

6235 Knotty Pine Dr SE, Winter Haven, FL

Kelly Jones · KELLER WILLIAMS REALTY SMART 1

56Active

$215,000

3 bd · 3 ba · 1,549 sqft

2216 Starboard, Winter Haven, FL

Bree Allison · KELLER WILLIAMS TAMPA CENTRAL

Price Reduced35Active

$339,900

5 bd · 3 ba · 2,696 sqft

321 Alexzander Way, Winter Haven, FL

Joshua Nogowski · TAH FLORIDA LLC

Price Reduced29Active

$249,900

3 bd · 2 ba · 1,495 sqft

5308 Green Dr, Winter Haven, FL

Misty McCracken · FATHOM REALTY FL LLC

52Active

$449,900

3 bd · 2 ba · 2,069 sqft

1061 Sawgrass Dr, Winter Haven, FL

Barb Wiechmann · ROOST REALTY GROUP LLC

Price Reduced57Active

$110,000

2 bd · 2 ba · 1,056 sqft

4242 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

18Active

$92,000

2 bd · 2 ba · 840 sqft

1700 6th St NW #C21, Winter Haven, FL

Don Jerue · KELLER WILLIAMS REALTY SMART 1

Price Reduced57Active

$310,000

3 bd · 2 ba · 2,109 sqft

3614 Plymouth Dr, Winter Haven, FL

Andrew Duncan · LPT REALTY LLC

64Active

$140,000

2 bd · 2 ba · 1,344 sqft

4146 Sprucewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

40Active

$119,000

2 bd · 2 ba · 1,190 sqft

700 Mirror Ter NW #506, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

74Active

$124,900

2 bd · 2 ba · 1,403 sqft

4158 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

67Active

$129,000

2 bd · 2 ba · 1,344 sqft

4132 Sprucewood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

32Active

$99,000

3 bd · 2 ba · 1,226 sqft

333 Lake Howard Dr NW #314D, Winter Haven, FL

Justin Cans · IMPACT REALTY TAMPA BAY

40Active

$164,900

2 bd · 2 ba · 1,351 sqft

700 Mirror Ter NW #507, Winter Haven, FL

Scott Kline · KLINE REAL ESTATE SERVICES

60Active

$334,900

3 bd · 2 ba · 1,700 sqft

5312 Nicklaus Dr, Winter Haven, FL

Emily Bastos Porto · COLDWELL BANKER RESIDENTIAL RE

28Active

$90,000

2 bd · 2 ba · 1,352 sqft

134 Lake Hazel Dr, Winter Haven, FL

Kelley Blackburn · COLDWELL BANKER REALTY

61Active

$309,900

2 bd · 2 ba · 1,819 sqft

4130 Bedford Ave, Winter Haven, FL

Bryan Dicks · COLDWELL BANKER REALTY

Price Reduced36Active

$94,900

2 bd · 2 ba · 1,372 sqft

150 El Dorado #105, Winter Haven, FL

Rosalia Abreu · ALLSTATE REALTY SERVICES

Price Reduced43Active

$129,900

2 bd · 2 ba · 1,265 sqft

4212 Cedarwood St, Winter Haven, FL

Karl Erickson · FLORIDA HOMES REALTY & MORTGAGE

40Active

$235,000

2 bd · 2 ba · 1,385 sqft

3023 Caneel St, Winter Haven, FL

Marco Silva Bravo · GOYAL & DECOSTER REALTY

1 2 3 4…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.