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
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...
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...
Reduced -$8,100
5308 Green Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential
MLS# O6420480 / Active
A 55+ resort style, guarded and gated community, plus incredible value make this home a MUST SEE! Welcome to a well maintained, bright and cheery 3...
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...
689 Lake Howard Drive UNIT 1E
Winter Haven, FL 33880
Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B
Residential
MLS# TB8360466 / Active
Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend o...
3440 Grenville Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential
MLS# O6401312 / Active
Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan wit...
Reduced -$10,100
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MLS IDX data last updated on 07-13-2026 7:53 PM EST.
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