55+ Community Homes in Winter Haven, FL

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24 of 125 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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New66Active
$310,000
3 bd · 2 ba · 1,680 sqft
5344 Nicklaus Dr, Winter Haven, FL
Lori Raath · LAKE ASHTON REALTY INC.
New17Active
$249,900
2 bd · 2 ba · 1,719 sqft
4035 Carteret Dr, Winter Haven, FL
Bryan Rhoads · LKV REALTY, LLC
72Active
$434,700
3 bd · 2 ba · 2,312 sqft
1321 Oakmont Dr, Winter Haven, FL
Lori Raath · LAKE ASHTON REALTY INC.

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.

About 55+ Community Homes in Winter Haven, FL

55+ Community Homes in Winter Haven, FL: 125 active listings as of October 4, 2026, 05:17 UTC.

Property types among these 125 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property type	Listings	Share
Manufactured Home	49	39.2%
Single Family Residence	37	29.6%
Condominium	27	21.6%

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

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

55+ Community Homes in Winter Haven, FL

Your local brokerage

Listing data & MLS disclosures

About 55+ Community Homes in Winter Haven, FL

Winter Haven housing market

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

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

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Winter Haven, FL community profile

Explore Winter Haven homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Winter Haven, FL community profile

Winter Haven housing market

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

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

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026