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 -$5,000
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...
3008 Caneel Street
Winter Haven, FL 33884
Traditions Ph 2a
Residential
MLS# P4937668 / Active
Situated in the desirable, maintenance-free gated community of Traditions, this gorgeous 2-bedroom, 2-bath villa with a flex room offers the perfec...
257 Meadowbrook Boulevard
Winter Haven, FL 33881
Lucerne Park Reserve
Residential
MLS# P4937588 / Active
PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home ...
Reduced -$2,000
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
2349 Salzburg Loop
Winter Haven, FL 33884
Vienna Square Ph 01
Residential
MLS# P4937532 / Active
HERONS, CRANES, EGRETS, AND DUCKS! You'll have a birds eye view of Florida's most beautiful waterfowl from this custom 3 bedroom 3 bath home locate...
Reduced -$5,000
39 Kimberly Court
Winter Haven, FL 33880
Brandy Chase Village A Rep
Residential
MLS# P4937502 / Active
Welcome to Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. T...
Reduced -$5,000
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
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MLS IDX data last updated on 06-15-2026 8:08 AM EST.
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