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 81-90 of 132
63 Photos 4918 Rosewood Street Winter Haven, FL 33880

4918 Rosewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4938247 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1008 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

This home is a MUST SEE? You will find many updates in this home from the beautiful granite counters in the kitchen and new kitchen cabinets to the... 

More Details

$125,000
Provided courtesy of COLDWELL BANKER REALTY
25 Photos 1700 6th Street UNIT B23 Winter Haven, FL 33881

1700 6th Street UNIT B23
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# O6391774 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 960 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

This beautifully maintained **DELUXE UNIT** is move-in ready and offers everything youve been searching forlocated in a desirable **55+ community**... 

More Details

$125,000
Provided courtesy of CENTRIC REALTY SERVICES LLC
70 Photos 4158 Rolling Oaks Drive Winter Haven, FL 33880

4158 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4938916 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1403 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Walk right in to this fully furnished home located in Oakwood Estates, a 55+ community. The kitchen is laid out perfect for entertaining and contai... 

More Details

$124,900
Provided courtesy of COLDWELL BANKER REALTY
10 Photos 689 Lake Howard Drive UNIT 1E Winter Haven, FL 33880

689 Lake Howard Drive UNIT 1E
Winter Haven, FL 33880
Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B
Residential

MLS# TB8360466 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 1050 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B

Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend o... 

More Details

$124,000
Provided courtesy of RIVERA & ASSOCIATES REALTY
1 Photos 100 Lakeside Ranch Drive Winter Haven, FL 33881

100 Lakeside Ranch Drive
Winter Haven, FL 33881
Lakeside Ranch For Mobile Homes
Residential

MLS# O6303367 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1176 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeside Ranch For Mobile Homes

LAKEFRONT COMMUNITY...Welcome home to Lakeside Ranch, a gated 55+ community with NO LOT RENT! This 2 Bedroom/2 Bath home features a large living ro... 

More Details

$120,000
Provided courtesy of HOME WISE REALTY GROUP, INC.
65 Photos 4155 Sprucewood Street Winter Haven, FL 33880

4155 Sprucewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4938325 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1200 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open an... 

More Details

$120,000
Provided courtesy of COLDWELL BANKER REALTY
40 Photos 700 Mirror Terrace UNIT #506 Winter Haven, FL 33881

700 Mirror Terrace UNIT #506
Winter Haven, FL 33881
Spring Lake Towers
Residential

MLS# P4939037 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1190 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Spring Lake Towers

PRICED TO SELL!! **GORGEOUS VIEWS FROM THIS FURNISHED DIRECT LAKEFRONT CONDO** THE 2ND BEDROOM EXTENDS THE LIVING AREA AND CAN BE CLOSED FOR GUEST ... 

More Details

$119,000
Provided courtesy of JUDY B CLEAVES PROPERTIES INC
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

$119,000
Reduced -$6,000
Provided courtesy of COLDWELL BANKER REALTY
62 Photos 4228 Cedarwood Street Winter Haven, FL 33880

4228 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4937684 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1104 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Move right into this very well maintained home. This home features some new vinyl flooring and newer windows. The hall bathroom has been upgraded w... 

More Details

$118,000
Provided courtesy of COLDWELL BANKER REALTY
43 Photos 333 Lake Howard Drive UNIT 203C Winter Haven, FL 33880

333 Lake Howard Drive UNIT 203C
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# L4961519 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and th... 

More Details

$118,000
Provided courtesy of COLDWELL BANKER REALTY

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 06-18-2026 7:51 PM 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®