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 31-40 of 132
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
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
70 Photos 1709 Linz Ct Winter Haven, FL 33884

1709 Linz Ct
Winter Haven, FL 33884
Vienna Square
Residential

MLS# P4936273 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1164 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square

NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happyhomeowner. Bright, fresh, and relax... 

More Details

$259,000
Provided courtesy of CENTURY 21 WATSON & MYERS REALTY
46 Photos 1678 Linz Court Winter Haven, FL 33884

1678 Linz Court
Winter Haven, FL 33884
Vienna Square Ph 2c
Residential

MLS# L4960316 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1158 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 2c

BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Squar... 

More Details

$258,500
Provided courtesy of COLDWELL BANKER REALTY
21 Photos 133 El Dorado Winter Haven, FL 33884

133 El Dorado
Winter Haven, FL 33884
Florida Highland Co
Residential

MLS# R4911459 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1639 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Florida Highland Co

Charming and well-maintained and can be your HOME in Winter Haven! This property features a functional open concept floor plan with spacious living... 

More Details

$255,000
Provided courtesy of HOMES UNLIMITED REAL ESTATE CORP
40 Photos 3363 Livingston Way Winter Haven, FL 33884

3363 Livingston Way
Winter Haven, FL 33884
Traditions Phase 1
Residential

MLS# TB8478803 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1118 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Phase 1

Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throug... 

More Details

$245,000
Reduced -$10,000
Provided courtesy of AGILE GROUP REALTY
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

$239,900
Reduced -$9,000
Provided courtesy of LOVELAND PROPERTIES
42 Photos 6825 S Lake Henry Drive Winter Haven, FL 33881

6825 S Lake Henry Drive
Winter Haven, FL 33881
Lucerne Park Fruit Assn
Residential

MLS# S5143698 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1790 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lucerne Park Fruit Assn

One or more photo(s) has been virtually staged. Enjoy true Florida lakefront living in this spacious 2-bedroom, 2-bath home offering almost 1800 sq... 

More Details

$239,000
Reduced -$10,900
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
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 Havens most desirable gated 55+ communities! Built in 2020, this impeccably maintaine... 

More Details

$235,000
Provided courtesy of DALTON WADE INC
44 Photos 1561 Vienna Square Drive Winter Haven, FL 33884

1561 Vienna Square Drive
Winter Haven, FL 33884
Vienna Square Ph 2a
Residential

MLS# P4932767 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1231 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 2a

R E D U C E D ... YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. T... 

More Details

$225,000
Reduced -$2,000
Provided courtesy of FLORIDA HOME CHOICE 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 06-18-2026 7:51 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®