David Shippey
863.521.4517

Retirement Homes for Sale in Winter Haven FL


Winter Haven FL Real Estate featuring Retirement Homes are listed below. These Retirement 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 Retirement homes for sale, please call 863-521-4517 or just click the "Schedule a Showing" or "Request 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 1-10 of 150
26 Photos 333 Lake Howard Drive UNIT 202C Winter Haven, FL 33880

333 Lake Howard Drive UNIT 202C
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# B4901659 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

Price Improvement-Welcome home to your cozy retreat nestled in an inviting 55+ community, just steps away from picturesque Lake Howard, offering tr... 

More Details

$94,950
Reduced -$5,000
Provided courtesy of LANDSEARCH LLC
11 Photos 4067 Rolling Oaks Drive Winter Haven, FL 33880

4067 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# B4901770 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 992 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

This home is move in ready! Being sold furnished. This home has a lot of updates. Newer,washer,dryer,refrig.,stove with warranty still on refrigera... 

More Details

$92,900
Reduced -$4,000
Provided courtesy of SOUTHERN BELLE REALTY
21 Photos 17 Kendra Court Winter Haven, FL 33880

17 Kendra Court
Winter Haven, FL 33880
Brandy Chase Village A Rep
Residential

MLS# B4901832 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 960 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Brandy Chase Village A Rep

2 Bedroom, 2 Bath home in Brandy Chase Village, a well-maintained 55+ community with clubhouse and heated pool. This home is surrounded on each sid... 

More Details

$130,000
Provided courtesy of KLINE REAL ESTATE SERVICES
45 Photos 470 Village Circle Winter Haven, FL 33880

470 Village Circle
Winter Haven, FL 33880
Village Park
Residential

MLS# B4901854 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1128 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Village Park

Move-In Ready! This charming home is nestled in a vibrant 55+ community, offering an array of amenities including a community pool, tennis courts, ... 

More Details

$138,500
Provided courtesy of CRAIG BURKE REAL ESTATE GROUP, LLC
35 Photos 4250 Cedarwood Street Winter Haven, FL 33880

4250 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# B4902006 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1200 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

You will feel right at home in this roomy 2/2, bring clothes, tooth brush and groceries and your home. Home's CHA unit is approximately 3 years old... 

More Details

$109,900
Provided courtesy of SOUTHERN BELLE REALTY
31 Photos 128 Lake Hazel Drive Winter Haven, FL 33884

128 Lake Hazel Drive
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# G5092376 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1680 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Loc... 

More Details

$104,900
Reduced -$5,000
Provided courtesy of MOSAIC SERVICES LLC
47 Photos 163 Sweet Circle Winter Haven, FL 33884

163 Sweet Circle
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# G5099095 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1456 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Loc... 

More Details

$110,000
Provided courtesy of MOSAIC SERVICES LLC
36 Photos 6265 Pinehurst Loop Winter Haven, FL 33884

6265 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# L4944406 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2521 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

**** WOW ****LOOK AT THE NEW PRICE ""REDUCTION"" ****SELLER MOTIVATED with NEW PRICING ******AMAZING NEWER HOME ***** BEAUTIFUL 3/2 + LARGE DEN/ EX... 

More Details

$599,000
Reduced -$51,000
Provided courtesy of ROOST REALTY GROUP LLC
50 Photos 4119 Rolling Oaks Drive Winter Haven, FL 33880

4119 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Ests
Residential

MLS# L4945333 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1364 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Ests

A ""FIVE STAR"" GATED, RESIDENT OWNED COMMUNITY IN WINTER HAVEN, FLORIDA! Own your lot with this spacious two bedroom two bath manufactured home, w... 

More Details

$124,000
Provided courtesy of CHARLES RUTENBERG REALTY ORLANDO
28 Photos 134 Lake Hazel Drive Winter Haven, FL 33884

134 Lake Hazel Drive
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# L4948241 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1352 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located ... 

More Details

$99,900
Provided courtesy of COLDWELL BANKER REALTY

Broker Reciprocity The information being provided by © 2025 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 REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, 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 07-20-2025 3:32 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 Retirement Homes for sale in Winter Haven Florida, visit our website daily.

The retirement homes above are brought to you by David Shippey REALTOR®.

Related Searches

Active Adult and Retirement Winter Haven Florida Homes For Sale.
Winter Haven Florida Active Adult Homes and 55 Plus.
Active Adult and Retirement Winter Haven FL Houses For Sale.
Winter Haven FL Houses for Active Adults.