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.
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
1700 6th Street UNIT C2
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential
MLS# L4960231 / Active
Welcome to easy, low-maintenance Florida living in this fully furnished 1 bedroom, 1 bathroom ground-floor condo located in the well-established Wi...
1347 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2 South
Residential
MLS# L4960249 / Active
Are you looking for a move-in ready home? Well, you found it! This home is like a new build, only better. It is clean as a whistle, has tasteful li...
1678 Linz Court
Winter Haven, FL 33884
Vienna Square Ph 2c
Residential
MLS# L4960316 / Active
BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Squar...
4511 Redwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential
MLS# L4960495 / Active
Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a pe...
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
6450 Hollyberry Lane
Winter Haven, FL 33881
Brookhaven Village
Residential
MLS# L4960650 / Active
One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Villagea highly sought-after 55+ community where you ...
Reduced -$1,000
6643 Westchester Drive
Winter Haven, FL 33881
Lake N Golf Estates Add
Residential
MLS# L4960802 / Active
Welcome to easy Florida lake view living in this beautifully updated 2-bedroom, 2-bath home located in a friendly 55+ no pet community on the shore...
6561 Chinaberry Dr Ne
Winter Haven, FL 33881
Brookhaven Village First Add
Residential
MLS# L4960831 / Active
Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desira...
5268 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential
MLS# L4960893 / Active
DON""T SCROLL PAST THIS BEAUTIFUL DESIGNER HOME in the PREMIER Active 55+ Community in LAKE ASHTON. You will LOVE THE EXPANSIVE WATER VIEW OVER THE...
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 06-10-2026 8:43 AM 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®