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 130
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
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 Haven’s premier 55+ gated communit... 

More Details

$262,500
Reduced -$2,500
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
27 Photos 4020 Carteret Drive Winter Haven, FL 33884

4020 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# O6389154 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2282 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Seller is willing to offer funds towards Buyer`s Closing Costs. Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bat... 

More Details

$405,900
Reduced -$14,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III
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
57 Photos 3614 Plymouth Drive Winter Haven, FL 33884

3614 Plymouth Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# TB8522011 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Perfectly situated on a premium pond-front homesite in the sought-after 55+ gated community of Traditions at Lake Ruby, this beautifully maintained... 

More Details

$320,000
Provided courtesy of LPT REALTY LLC
39 Photos 3440 Grenville Drive Winter Haven, FL 33884

3440 Grenville Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# O6401312 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1275 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan wit... 

More Details

$229,800
Reduced -$10,100
Provided courtesy of LOVELAND PROPERTIES
68 Photos 3890 Bedford Avenue Winter Haven, FL 33884

3890 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# L4961088 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2322 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, c... 

More Details

$395,000
Provided courtesy of DREAM REALTY GROUP
57 Photos 2733 Attwater Loop Winter Haven, FL 33884

2733 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# P4937444 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2032 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated... 

More Details

$359,500
Reduced -$2,196
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
41 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

NEW PRICE IMPROVEMENT! WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE D... 

More Details

$263,900
Reduced -$10,000
Provided courtesy of LPT REALTY, LLC
40 Photos 3023 Caneel Street Winter Haven, FL 33884

3023 Caneel Street
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# TB8504638 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Welcome to the vibrant lifestyle of Traditions, one of Winter Haven’s most desirable gated 55+ communities! Built in 2020, this impeccably maintain... 

More Details

$235,000
Provided courtesy of DALTON WADE INC

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 07-13-2026 7:53 PM 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®