55 Plus Homes for Sale Winter Haven FL


Winter Haven FL Real Estate featuring 55 Plus Homes are listed below. These 55 Plus homes for sale in Winter Haven Florida are updated everyday from our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL 55 Plus homes for sale, please call 863-521-4517 or just click the "Schedule a Tour" or "More Info" button on any property detail pages.

Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.

Modify Search Criteria

Displaying results 101-110 of 132
27 Photos 1703 Linz Court Winter Haven, FL 33884

1703 Linz Court
Winter Haven, FL 33884
Vienna Square Phase 3a
Residential

MLS# P4933885 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1164 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Phase 3a

NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live... 

More Details

$259,000
Provided courtesy of DGCF REALTY ADVISORS LLC
54 Photos 4019 Carteret Drive Winter Haven, FL 33884

4019 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# S5145776 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1719 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Havens premier 55+ gated communiti... 

More Details

$265,000
Reduced -$4,999
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
40 Photos 3588 Raleigh Drive Winter Haven, FL 33884

3588 Raleigh Drive
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# L4959265 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1719 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

Welcome to 3588 Raleigh Dr! Located within the gated 55+ community of Traditions, this well-maintained corner-lot home offers a blend of comfort, f... 

More Details

$268,500
Reduced -$4,000
Provided courtesy of THE MARKET REALTY COMPANY
40 Photos 3923 Baldwin Lane Winter Haven, FL 33884

3923 Baldwin Lane
Winter Haven, FL 33884
Traditions Ph 1
Residential

MLS# P4935847 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1719 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 1

WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITIO... 

More Details

$273,900
Reduced -$25,100
Provided courtesy of LPT REALTY, LLC
35 Photos 2790 Adeline Avenue Winter Haven, FL 33881

2790 Adeline Avenue
Winter Haven, FL 33881
Willowbrook South
Residential

MLS# O6391726 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1328 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Willowbrook South

Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an ar... 

More Details

$274,900
Reduced -$3,000
Provided courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
40 Photos 2470 Salzburg Loop Winter Haven, FL 33884

2470 Salzburg Loop
Winter Haven, FL 33884
Vienna Square Ph 01
Residential

MLS# O6344501 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1935 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 01

This property is located in one of the best neighborhoods in Winter haven. 

More Details

$280,000
Reduced -$9,999
Provided courtesy of PREMIUM REAL ESTATE SERVICES
54 Photos 2925 Dayton Drive Winter Haven, FL 33884

2925 Dayton Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4937324 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Discover the charm of this delightful 3-bedroom, 2-bath home located in the maintenance-free, 55+ gated community of Traditions at Lake Ruby. Thoug... 

More Details

$284,500
Reduced -$15,400
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
41 Photos 257 Meadowbrook Boulevard Winter Haven, FL 33881

257 Meadowbrook Boulevard
Winter Haven, FL 33881
Lucerne Park Reserve
Residential

MLS# P4937588 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1725 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lucerne Park Reserve

PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home ... 

More Details

$287,950
Reduced -$2,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
51 Photos 912 Avenue T Winter Haven, FL 33880

912 Avenue T
Winter Haven, FL 33880
Woodmere
Residential

MLS# S5113072 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2149 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Woodmere

Location, Location! This charming 3-bedroom, 2-bath home, large living room and a huge family room ( could be a 4th bedroom) is situated in the vib... 

More Details

$295,000
Provided courtesy of CENTURY 21 WOLF'S CROSSING REALTY
61 Photos 4130 Bedford Avenue Winter Haven, FL 33884

4130 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# L4962090 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1819 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT ""TRADITIONS OF RUBY LAKE"". ... 

More Details

$309,900
Provided courtesy of COLDWELL BANKER REALTY

Broker Reciprocity The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 06-19-2026 2:00 AM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

For a fresh updated list of 55 Plus Homes for sale in Winter Haven Florida, visit our website daily.

These 55 plus homes above are brought to you by David Shippey REALTOR®