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.
700 Mirror Terrace UNIT #505
Winter Haven, FL 33881
Spring Lake Towers
Residential
MLS# TB8445379 / Active
Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this l...
Reduced -$20,000
4410 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4937929 / Active
Pack your bags and move right into this very well maintained home located in Oakwood Estates, a 55+ community. The floorplan offers two living area...
Reduced -$5,000
4173 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4938419 / Active
Check this out!! The home has new vinyl plank and new carpet in the bedrooms and a new roof in 2025. Enjoy the nice sized living room with relaxing...
Reduced -$15,000
4246 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# O6325757 / Active
Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroo...
4063 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4937489 / Active
Move right into this very well maintained home. This home comes furnished with most of what you see including dishes, pots and pans, and silverware...
Reduced -$4,005
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
4511 Redwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# L4960495 / Active
Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a pe...
95 Parson Drive
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential
MLS# P4935492 / Active
This 3-bedroom, 2-bath home located in the community of Orange Manor West is perfect for settling into an active community for the 55+. The home fe...
1700 6th Street UNIT C26
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential
MLS# P4934743 / Active
This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, mak...
333 Lake Howard Drive UNIT 203C
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential
MLS# L4961519 / Active
Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and th...
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 06-11-2026 8:46 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®