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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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...
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 -$9,000
6433 Jacaranda Avenue
Winter Haven, FL 33881
Brookhaven Village
Residential
MLS# S5144807 / Active
Significant price improvement and a highly motivated seller make this an exceptional opportunity in the sought-after 55+ Brookhaven Village communi...
Increase +$5,100
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
6081 Southern Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential
MLS# L4959229 / Active
Welcome to 6081 Southern Oaks Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks wh...
2790 Adeline Avenue
Winter Haven, FL 33881
Willowbrook South
Residential
MLS# O6391726 / Active
Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an ar...
Reduced -$3,000
5365 Hogan Lane
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential
MLS# P4938226 / Active
Welcome to the next exciting chapter of your life in Lake Ashton, Central Floridas premier 55+ active-adult community, where this immaculately main...
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MLS IDX data last updated on 06-19-2026 8:15 AM EST.
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