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 130
65 Photos 4127 Sprucewood Street Winter Haven, FL 33880

4127 Sprucewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4936494 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1035 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit o... 

More Details

$85,000
Reduced -$5,000
Provided courtesy of COLDWELL BANKER REALTY
44 Photos 6775 Brentwood Drive Winter Haven, FL 33881

6775 Brentwood Drive
Winter Haven, FL 33881
Lake N Golf Estates
Residential

MLS# S5146696 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1320 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates

One or more photo(s) has been virtually staged. Welcome to 6775 Brentwood Dr NE, located in the desirable, no pet community of Lake N Golf Estates,... 

More Details

$132,500
Reduced -$4,400
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
33 Photos 400 El Camino Drive UNIT #210 Winter Haven, FL 33884

400 El Camino Drive UNIT #210
Winter Haven, FL 33884
Orchid Spgs Vill 400 San Miguel
Residential

MLS# S5142500 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1666 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Spgs Vill 400 San Miguel

Short Sale. Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living ... 

More Details

$120,000
Reduced -$10,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
43 Photos 4420 Limewood Street Winter Haven, FL 33880

4420 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# S5142224 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 864 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Welcome home to 4420 Limewood St in Winter Haven, located in the desirable 55+ co-op community of Oakwood Estates—a neighborhood known for active l... 

More Details

$105,000
Reduced -$7,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
64 Photos 4146 Sprucewood Street Winter Haven, FL 33880

4146 Sprucewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4939076 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1344 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

You won't want to miss this opportunity. This 1344 sf home located in Oakwood Estates, a 55+ community. From the carport walk into the lanai, perfe... 

More Details

$140,000
Provided courtesy of COLDWELL BANKER REALTY
68 Photos 3890 Bedford Avenue Winter Haven, FL 33884

3890 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# L4961088 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2322 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, c... 

More Details

$395,000
Provided courtesy of DREAM REALTY GROUP
20 Photos 6394 Lolly Bay Loop Winter Haven, FL 33881

6394 Lolly Bay Loop
Winter Haven, FL 33881
Brookhaven Village Second Add
Residential

MLS# L4958069 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1620 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village Second Add

Located in the 55+ community of Brookhaven Village, this fee-simple manufactured home offers 1,620 square feet of living space with a functional la... 

More Details

$179,900
Reduced -$10,000
Provided courtesy of COLDWELL BANKER REALTY
43 Photos 6308 Pinehurst Loop Winter Haven, FL 33884

6308 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# A4678252 / 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

Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton ... 

More Details

$456,900
Reduced -$3,000
Provided courtesy of FLATFEE.COM
70 Photos 1709 Linz Ct Winter Haven, FL 33884

1709 Linz Ct
Winter Haven, FL 33884
Vienna Square
Residential

MLS# P4936273 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1164 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square

NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and rela... 

More Details

$259,000
Provided courtesy of CENTURY 21 WATSON & MYERS 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.

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 07-14-2026 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®