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.

Modify Search Criteria

Displaying results 61-70 of 132
69 Photos 6216 Pinehurst Loop Winter Haven, FL 33884

6216 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# P4937694 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

Stunning Sebastian Floor Plan Home in an Exclusive, Secure 55+ Florida Community, Lake Ashton. Discover this exceptional single-family home built i... 

More Details

$459,000
Provided courtesy of LAKE ASHTON REALTY INC.
37 Photos 345 24th Street UNIT #25 Winter Haven, FL 33880

345 24th Street UNIT #25
Winter Haven, FL 33880
Imperial Villas
Residential

MLS# P4937740 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1008 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Villas

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... 

More Details

$145,000
Reduced -$13,000
Provided courtesy of DALTON WADE INC
40 Photos 3588 Raleigh Drive Winter Haven, FL 33884

3588 Raleigh Drive
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# L4959265 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1719 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

Welcome to 3588 Raleigh Dr! Located within the gated 55+ community of Traditions, this well-maintained corner-lot home offers a blend of comfort, f... 

More Details

$268,500
Reduced -$4,000
Provided courtesy of THE MARKET REALTY COMPANY
38 Photos 6081 Southern Oaks Drive Winter Haven, FL 33884

6081 Southern Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# L4959229 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1080 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Welcome to 6081 Southern Oaks Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks wh... 

More Details

$169,500
Provided courtesy of LOCKHART & ASSOCIATES INC
52 Photos 6086 Southern Oaks Drive Winter Haven, FL 33884

6086 Southern Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# L4959284 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1040 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Welcome to 6086 Southern Oaks Drive SE, a beautifully updated and well- maintained, move in ready manufactured home located in the highly sought af... 

More Details

$185,000
Provided courtesy of LOCKHART & ASSOCIATES INC
23 Photos 825 3rd Street Winter Haven, FL 33881

825 3rd Street
Winter Haven, FL 33881
Ida Lake Sub
Residential

MLS# O6380870 / Active
3 Beds, 1.00 Total Baths, 1 Full Bath, 1152 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Ida Lake Sub

The property is in the process of being split (Lot Split) there is a vacant separate lot to the left of the house. The asking price for the current... 

More Details

$330,000
Reduced -$25,000
Provided courtesy of FLORIDA REALTY INVESTMENTS
42 Photos 6825 S Lake Henry Drive Winter Haven, FL 33881

6825 S Lake Henry Drive
Winter Haven, FL 33881
Lucerne Park Fruit Assn
Residential

MLS# S5143698 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1790 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lucerne Park Fruit Assn

One or more photo(s) has been virtually staged. Enjoy true Florida lakefront living in this spacious 2-bedroom, 2-bath home offering almost 1800 sq... 

More Details

$239,000
Reduced -$10,900
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
59 Photos 5828 Marsh Landing Drive Winter Haven, FL 33881

5828 Marsh Landing Drive
Winter Haven, FL 33881
Lakeside Landings Ph 01
Residential

MLS# L4958953 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2078 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeside Landings Ph 01

Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your ... 

More Details

$387,500
Provided courtesy of FLORIDA REAL ESTATE COMPANY
70 Photos 4056 Rolling Oaks Drive Winter Haven, FL 33880

4056 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4937783 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1104 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

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... 

More Details

$125,000
Reduced -$5,000
Provided courtesy of COLDWELL BANKER REALTY
22 Photos 1700 6th Street UNIT C31 Winter Haven, FL 33881

1700 6th Street UNIT C31
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# L4959370 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 840 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

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... 

More Details

$99,900
Reduced -$9,890
Provided courtesy of KELLER WILLIAMS REALTY SMART 1

Broker Reciprocity 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 06-08-2026 2:00 AM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

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®