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.
Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.
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 -$5,000
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...
435 Village Circle
Winter Haven, FL 33880
Village Park
Residential
MLS# L4962605 / Active
ENJOY FLORIDA LIVING AS IT`S FINEST...Welcome yourself home to this 2 Bedroom/ 2 Bath home offering over 1,300 sq ft of comfortable living space an...
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
3023 Caneel Street
Winter Haven, FL 33884
Traditions Ph 2a
Residential
MLS# TB8504638 / Active
Welcome to the vibrant lifestyle of Traditions, one of Winter Haven’s most desirable gated 55+ communities! Built in 2020, this impeccably maintain...
4019 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential
MLS# S5145776 / Active
Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communit...
Reduced -$2,500
6235 Knotty Pine Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential
MLS# P4939218 / Active
CUTE AND COZY 2 BR/2 BA HOME IN GARDEN GROVE OAKS 55+ COMMUNITY! This one-owner home is in one of Winter Haven`s most sought-after 55+ communities ...
The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's
personal, non-commercial use and may not be used for any purpose other than to
identify prospective properties consumer may be interested in purchasing. Any information relating
to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX)
program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.
MLS IDX data last updated on 07-13-2026 7:53 PM EST.
For a fresh updated list of 55 Plus Homes for sale in Winter Haven Florida, visit our website daily.
These 55 plus homes above are brought to you by David Shippey REALTOR®