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
6261 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential
MLS# L4959857 / Active
Experience the best of Florida resort-style living in this exceptional Ashton floor plan located in the sought-after Lake Ashton Golf Club Communit...
Reduced -$5,000
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
4239 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4937986 / Active
Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The pr...
3363 Livingston Way
Winter Haven, FL 33884
Traditions Phase 1
Residential
MLS# TB8478803 / Active
Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throug...
Reduced -$10,000
4410 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# P4937929 / Active
Pack your bags and move right into this very well maintained home located in Oakwood Estates, a 55+ community. The floorplan offers two living area...
Reduced -$5,000
1581 Oakview Circle
Winter Haven, FL 33880
Oakview
Residential
MLS# G5108372 / Active
Move-in ready with a NEW ROOF (2024), updated major systems, and brand-new kitchen appliances, this beautifully maintained villa offers the low-mai...
Reduced -$4,900
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 Florida 55+ community ...
Reduced -$10,000
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
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 -$6,000
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MLS IDX data last updated on 07-14-2026 2:00 AM EST.
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