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 Dr Nw UNIT 314D
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential
MLS# TB8515282 / Active
Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Wint...
1700 6th Street UNIT B24
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential
MLS# O6371915 / Active
55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining...
Reduced -$11,000
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
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...
409 Village Circle
Winter Haven, FL 33880
Village Park
Residential
MLS# L4960521 / Active
Charming and well maintained! 2-Bedroom 2- Bath Home in Desirable 55+ Community - You Own the Land with low HOA fees!This inviting home features fr...
Reduced -$7,000
1700 6th Street UNIT C31
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential
MLS# L4959370 / Active
HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully upda...
Reduced -$9,890
345 24th Street UNIT #23
Winter Haven, FL 33880
Imperial Villas
Residential
MLS# L4960143 / Active
**PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well mainta...
Reduced -$14,900
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...
1700 6th Street UNIT C1
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential
MLS# L4958845 / Active
Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to y...
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MLS IDX data last updated on 06-19-2026 8:02 PM EST.
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