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.
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4056 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4937783 / Active
Pack your bags and move right into this fully furnished home. This home has many updates!! Although the bedrooms have updated carpets there is nice...
Reduced -$6,000
345 24th Street UNIT #25
Winter Haven, FL 33880
Imperial Villas
Residential
MLS# P4937740 / Active
Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperia...
Reduced -$13,000
6216 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential
MLS# P4937694 / Active
Stunning Sebastian Floor Plan Home in an Exclusive, Secure 55+ Florida Community, Lake Ashton. Discover this exceptional single-family home built i...
4228 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4937684 / Active
Move right into this very well maintained home. This home features some new vinyl flooring and newer windows. The hall bathroom has been upgraded w...
257 Meadowbrook Boulevard
Winter Haven, FL 33881
Lucerne Park Reserve
Residential
MLS# P4937588 / Active
PRICE IMPROVEMENT! Motivated seller! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built i...
Reduced -$3,450
1209 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential
MLS# P4937555 / Active
Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. A golf membership (expires Sept. 30, 2026) for a single golfer wil...
Reduced -$11,000
2733 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 02
Residential
MLS# P4937444 / Active
This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated...
Reduced -$2,196
7041 Fairview Village Circle
Winter Haven, FL 33881
Fairview Village
Residential
MLS# P4937431 / Active
Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake ...
Reduced -$2,000
4577 Back Nine Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential
MLS# P4937386 / Active
Virtually Staged. Welcome Home!!! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclu...
2925 Dayton Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential
MLS# P4937324 / Active
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...
Reduced -$15,400
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MLS IDX data last updated on 07-14-2026 2:00 AM EST.
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