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.

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Displaying results 81-90 of 132
54 Photos 2925 Dayton Drive Winter Haven, FL 33884

2925 Dayton Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4937324 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Discover the charm of this delightful 3-bedroom, 2-bath home located in the maintenance-free, 55+ gated community of Traditions at Lake Ruby. Thoug... 

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$284,500
Reduced -$15,400
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
60 Photos 4577 Back Nine Drive Winter Haven, FL 33884

4577 Back Nine Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4937386 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1918 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

Welcome Home!!! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retir... 

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$349,600
Reduced -$10,300
Provided courtesy of LAKE ASHTON REALTY INC.
21 Photos 7041 Fairview Village Circle Winter Haven, FL 33881

7041 Fairview Village Circle
Winter Haven, FL 33881
Fairview Village
Residential

MLS# P4937431 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 248 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Fairview Village

Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake ... 

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$57,900
Reduced -$2,000
Provided courtesy of WATSON REALTY CORP.
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... 

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$359,500
Reduced -$2,196
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
70 Photos 4063 Rolling Oaks Drive Winter Haven, FL 33880

4063 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4937489 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1320 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Move right into this very well maintained home. This home comes furnished with most of what you see including dishes, pots and pans, and silverware... 

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$114,995
Reduced -$4,005
Provided courtesy of COLDWELL BANKER REALTY
49 Photos 39 Kimberly Court Winter Haven, FL 33880

39 Kimberly Court
Winter Haven, FL 33880
Brandy Chase Village A Rep
Residential

MLS# P4937502 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1044 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Brandy Chase Village A Rep

Welcome to Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. T... 

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$154,900
Reduced -$5,000
Provided courtesy of ALLSTATE REALTY SERVICES
70 Photos 2349 Salzburg Loop Winter Haven, FL 33884

2349 Salzburg Loop
Winter Haven, FL 33884
Vienna Square Ph 01
Residential

MLS# P4937532 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 1724 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 01

HERONS, CRANES, EGRETS, AND DUCKS! You'll have a birds eye view of Florida's most beautiful waterfowl from this custom 3 bedroom 3 bath home locate... 

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$309,900
Reduced -$5,000
Provided courtesy of CENTURY 21 WATSON & MYERS REALTY
70 Photos 1209 Sawgrass Drive Winter Haven, FL 33884

1209 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential

MLS# P4937555 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II South

Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. A golf membership (expires Sept. 30, 2026) for a single golfer wil... 

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$439,000
Reduced -$11,000
Provided courtesy of LAKE ASHTON REALTY INC.
41 Photos 257 Meadowbrook Boulevard Winter Haven, FL 33881

257 Meadowbrook Boulevard
Winter Haven, FL 33881
Lucerne Park Reserve
Residential

MLS# P4937588 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1725 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lucerne Park Reserve

PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home ... 

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$287,950
Reduced -$2,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
48 Photos 3008 Caneel Street Winter Haven, FL 33884

3008 Caneel Street
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# P4937668 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Situated in the desirable, maintenance-free gated community of Traditions, this gorgeous 2-bedroom, 2-bath villa with a flex room offers the perfec... 

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$210,000
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES

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