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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333 Lake Howard Drive UNIT 302D
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential
MLS# L4962292 / Active
One or more photo(s) has been virtually staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This...
333 Lake Howard Drive UNIT 312B
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential
MLS# P4939038 / Active
Virtually Staged. Introducing a beautifully renovated 2-bedroom, 2-bath condo located on the lakefront of Lake Howard in Winter Haven. This top-flo...
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...
5264 Green Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential
MLS# P4937885 / Active
5264 Green Drive Winter Haven, Florida is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded 55+ community with res...
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...
1700 6th Street UNIT B23
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential
MLS# O6391774 / Active
This beautifully maintained **DELUXE UNIT** is move-in ready and offers everything youve been searching forlocated in a desirable **55+ community**...
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
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
419 Greenfield Road
Winter Haven, FL 33884
Cypresswood Mdws
Residential
MLS# TB8513442 / Active
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, b...
Reduced -$5,000
100 El Camino Drive UNIT #101
Winter Haven, FL 33884
Orchid Spgs Vill 100 Condo
Residential
MLS# S5147114 / Active
Owner motivated and ready to negotiate WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Lo...
Reduced -$15,490
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MLS IDX data last updated on 06-17-2026 7:58 PM EST.
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