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.
454 Village Circle
Winter Haven, FL 33880
Village Park
Residential
MLS# L4960932 / Active
NO LOT RENT. Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable...
Reduced -$4,000
5268 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential
MLS# L4960893 / Active
DON""T SCROLL PAST THIS BEAUTIFUL DESIGNER HOME in the PREMIER Active 55+ Community in LAKE ASHTON. You will LOVE THE EXPANSIVE WATER VIEW OVER THE...
6473 Peppertree Path
Winter Haven, FL 33881
Brookhaven Village First Add
Residential
MLS# P4938365 / Active
EASY TO SEE, SCHEDULE YOU'RE VIEWING NOW! NO LOT RENT HERE....YOU OWN IT! OFFERED PARTIALLY FURNISHED, KITCHEN APPLIANCES AND INSIDE LAUNDRY WASHER...
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
4925 Cypress Gardens Road UNIT #100
Winter Haven, FL 33884
Doves Rest Add
Residential
MLS# P4938418 / Active
Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Ai...
333 Lake Howard Drive UNIT 212A
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential
MLS# S5147514 / Active
Wake up to views of Lake Howard and enjoy maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. From the bright Flori...
Reduced -$3,000
447 Village Circle
Winter Haven, FL 33880
Village Park
Residential
MLS# P4938447 / Active
This home is a must see!! Very well maintained home located in Village Park, a 55+ community where dogs are allowed. The home features new thermal ...
3890 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02
Residential
MLS# L4961088 / Active
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...
4038 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# B4902243 / Active
Welcome to paradise, in this 2/2 with a enclosed front porch, to watch the beautiful Florida sunsets. The gated 55 plus community offers many ameni...
6114 Grand Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential
MLS# L4961323 / Active
Waterfront view home on a large lot in amenity-rich community with clubhouse, pool, shuffleboard and fishing pond. This 2 bedroom 2 bathroom home f...
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 11:32 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®