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 31-40 of 133
4 Photos 333 Lake Howard Drive UNIT 302D Winter Haven, FL 33880

333 Lake Howard Drive UNIT 302D
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# L4962292 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

One or more photo(s) has been virtually staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This... 

More Details

$89,900
Provided courtesy of REGAL REAL ESTATE LLC
39 Photos 333 Lake Howard Drive UNIT 312B Winter Haven, FL 33880

333 Lake Howard Drive UNIT 312B
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# P4939038 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

Virtually Staged. Introducing a beautifully renovated 2-bedroom, 2-bath condo located on the lakefront of Lake Howard in Winter Haven. This top-flo... 

More Details

$129,000
Provided courtesy of VILLAGE REALTY OF WINTER HAVEN
27 Photos 1703 Linz Court Winter Haven, FL 33884

1703 Linz Court
Winter Haven, FL 33884
Vienna Square Phase 3a
Residential

MLS# P4933885 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1164 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Phase 3a

NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live... 

More Details

$259,000
Provided courtesy of DGCF REALTY ADVISORS LLC
70 Photos 5264 Green Drive Winter Haven, FL 33884

5264 Green Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4937885 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2011 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

5264 Green Drive Winter Haven, Florida is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded 55+ community with res... 

More Details

$335,000
Provided courtesy of LAKE ASHTON REALTY INC.
51 Photos 912 Avenue T Winter Haven, FL 33880

912 Avenue T
Winter Haven, FL 33880
Woodmere
Residential

MLS# S5113072 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2149 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Woodmere

Location, Location! This charming 3-bedroom, 2-bath home, large living room and a huge family room ( could be a 4th bedroom) is situated in the vib... 

More Details

$295,000
Provided courtesy of CENTURY 21 WOLF'S CROSSING 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
57 Photos 2733 Attwater Loop Winter Haven, FL 33884

2733 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# P4937444 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2032 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated... 

More Details

$359,500
Reduced -$2,196
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
61 Photos 4321 Cherrywood Street Winter Haven, FL 33880

4321 Cherrywood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4931788 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1488 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the... 

More Details

$108,000
Reduced -$10,000
Provided courtesy of COLDWELL BANKER REALTY
61 Photos 419 Greenfield Road Winter Haven, FL 33884

419 Greenfield Road
Winter Haven, FL 33884
Cypresswood Mdws
Residential

MLS# TB8513442 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1924 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Mdws

Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, b... 

More Details

$344,990
Reduced -$5,000
Provided courtesy of BOARDWALK REALTY ASSOCIATES, LLC
29 Photos 100 El Camino Drive UNIT #101 Winter Haven, FL 33884

100 El Camino Drive UNIT #101
Winter Haven, FL 33884
Orchid Spgs Vill 100 Condo
Residential

MLS# S5147114 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1361 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Spgs Vill 100 Condo

Owner motivated and ready to negotiate WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Lo... 

More Details

$89,500
Reduced -$15,490
Provided courtesy of LPT REALTY, LLC

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 06-17-2026 7:58 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®