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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56 Photos 2216 Starboard Winter Haven, FL 33881

2216 Starboard
Winter Haven, FL 33881
Hartridge Landing
Residential

MLS# TB8524293 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1549 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hartridge Landing

Check out this wonderful opportunity to own a spacious 3-bedroom, 2.5-bath home in the desirable 55+ community of Hartridge Landings! This well-mai... 

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$215,000
Provided courtesy of KELLER WILLIAMS TAMPA CENTRAL
35 Photos 321 Alexzander Way Winter Haven, FL 33881

321 Alexzander Way
Winter Haven, FL 33881
Jace Lndg
Residential

MLS# TB8524056 / Active
5 Beds, 3.00 Total Baths, 3 Full Bath, 2696 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Jace Lndg

Virtually Staged. Welcome to 321 Alexzander Way, a spacious, well apportioned home in the heart of Winter Haven! This location is central to Tampa ... 

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$365,500
Provided courtesy of TAH FLORIDA LLC
35 Photos 1525 Oakview Circle Winter Haven, FL 33880

1525 Oakview Circle
Winter Haven, FL 33880
Oakview
Residential

MLS# TB8522413 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1333 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakview

Turn-key elegance in one of Winter Haven’s 55+ community! Welcome home to Oakview, an immaculate, highly sought-after hidden jewel. This smokefre... 

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$200,000
Provided courtesy of LPT REALTY, LLC
57 Photos 3614 Plymouth Drive Winter Haven, FL 33884

3614 Plymouth Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# TB8522011 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Perfectly situated on a premium pond-front homesite in the sought-after 55+ gated community of Traditions at Lake Ruby, this beautifully maintained... 

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$320,000
Provided courtesy of LPT REALTY LLC
32 Photos 333 Lake Howard Dr Nw UNIT 314D Winter Haven, FL 33880

333 Lake Howard Dr Nw UNIT 314D
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# TB8515282 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1226 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Wint... 

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$99,000
Provided courtesy of IMPACT REALTY TAMPA BAY
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... 

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$342,990
Reduced -$2,000
Provided courtesy of BOARDWALK REALTY ASSOCIATES, LLC
40 Photos 3023 Caneel Street Winter Haven, FL 33884

3023 Caneel Street
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# TB8504638 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Welcome to the vibrant lifestyle of Traditions, one of Winter Haven’s most desirable gated 55+ communities! Built in 2020, this impeccably maintain... 

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$235,000
Provided courtesy of DALTON WADE INC
40 Photos 3363 Livingston Way Winter Haven, FL 33884

3363 Livingston Way
Winter Haven, FL 33884
Traditions Phase 1
Residential

MLS# TB8478803 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1118 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Phase 1

Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throug... 

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$235,000
Reduced -$10,000
Provided courtesy of AGILE GROUP REALTY
42 Photos 6827 S Lake Henry Drive Winter Haven, FL 33881

6827 S Lake Henry Drive
Winter Haven, FL 33881
Lake N Golf Estates Add
Residential

MLS# TB8464788 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1450 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates Add

Discover lakeside living at its finest in this spacious 4-bedroom, 2-bath home located in the highly desirable 55+ community of Golf & Lake Estates... 

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$195,000
Reduced -$10,000
Provided courtesy of GREEN STAR REALTY, INC.
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... 

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$124,000
Provided courtesy of RIVERA & ASSOCIATES REALTY

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