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.
4338 Cherrywood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4928579 / Active
Check out the improvements recently completed!! The home is move in ready!! The flooring has all been replaced with new plush carpet and vinyl plan...
Reduced -$5,000
1776 6th Street UNIT #303
Winter Haven, FL 33881
Lakeridge Condo
Residential
MLS# P4929979 / Active
Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake ...
4321 Cherrywood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4931788 / Active
Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the...
Reduced -$10,000
912 Avenue T
Winter Haven, FL 33880
Woodmere
Residential
MLS# S5113072 / Active
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...
4908 Rosewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4932743 / Active
Check out this wonderfully maintained home located in Oakwood Estates, a 55+ community. The HVAC has just been replaced and the roof is 3 years old...
Reduced -$10,000
1561 Vienna Square Drive
Winter Haven, FL 33884
Vienna Square Ph 2a
Residential
MLS# P4932767 / Active
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...
Reduced -$2,000
6308 Bayberry Boulevard
Winter Haven, FL 33881
Brookhaven Village
Residential
MLS# P4933148 / Active
LOW-COST YEAR AROUND LIVING! VERY WELL MAINTAINED! Fully Furnished everything stays! Pet Friendly lot. Gorgeous updating, Very Clean & Move-In read...
Reduced -$4,000
17 Kendra Court
Winter Haven, FL 33880
Brandy Chase Village A Rep
Residential
MLS# B4901832 / Active
Just reduced approx. $30,000 below appraised value to allow for remodeling! This 2 Bedroom, 2 Bath home is located in Brandy Chase Village, a well-...
Reduced -$10,000
508 Lakeside Ranch Way
Winter Haven, FL 33881
Lakeside Ranch For Mobile Homes
Residential
MLS# P4933855 / Active
ENJOY THIS WELL KEPT FURNISHED MANUFACTURED HOME IN GATED 55 AND OVER COMMUNITY. THIS PROPERTY IS IN A CO-OP. OUTSIDE OF HOME RECENTLY PAINTED 2026...
Reduced -$9,000
1703 Linz Court
Winter Haven, FL 33884
Vienna Square Phase 3a
Residential
MLS# P4933885 / Active
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...
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 06-07-2026 2:00 AM EST.
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®