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 31-40 of 132
46 Photos 454 Village Circle Winter Haven, FL 33880

454 Village Circle
Winter Haven, FL 33880
Village Park
Residential

MLS# L4960932 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1620 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Village Park

NO LOT RENT. Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable... 

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$135,000
Reduced -$4,000
Provided courtesy of DALTON WADE INC
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... 

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$395,000
Provided courtesy of DREAM REALTY GROUP
43 Photos 6114 Grand Oaks Drive Winter Haven, FL 33884

6114 Grand Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# L4961323 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1288 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Waterfront view home on a large lot in amenity-rich community with clubhouse, pool, shuffleboard and fishing pond. This 2 bedroom 2 bathroom home f... 

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$175,000
Provided courtesy of CROSBY & ASSOCIATES, INC.
29 Photos 1213 8th Street Winter Haven, FL 33881

1213 8th Street
Winter Haven, FL 33881
North Gate Village
Residential

MLS# L4961397 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 972 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: North Gate Village

One or more photo(s) has been virtually staged. Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community ready for a new owner. ... 

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$199,900
Provided courtesy of KELLER WILLIAMS REALTY SMART
43 Photos 333 Lake Howard Drive UNIT 203C Winter Haven, FL 33880

333 Lake Howard Drive UNIT 203C
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# L4961519 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and th... 

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$118,000
Provided courtesy of COLDWELL BANKER REALTY
70 Photos 1394 Oakmont Drive Winter Haven, FL 33884

1394 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2
Residential

MLS# L4961930 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2606 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2

Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amen... 

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$549,500
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
38 Photos 333 Lake Howard Drive UNIT 304B Winter Haven, FL 33880

333 Lake Howard Drive UNIT 304B
Winter Haven, FL 33880
Imperial Harbours Ph I
Residential

MLS# L4961973 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1330 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harbours Ph I

Top-floor condo with INCREDIBLE lake views in the desirable 55+ community of Imperial Harbours on Lake Howard! This three-bedroom, two-bath condo o... 

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$80,000
Provided courtesy of LOCKHART & ASSOCIATES INC
61 Photos 4130 Bedford Avenue Winter Haven, FL 33884

4130 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# L4962090 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1819 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT ""TRADITIONS OF RUBY LAKE"". ... 

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$309,900
Provided courtesy of COLDWELL BANKER REALTY
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# L4962192 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1352 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

One or more photo(s) has been virtually staged. 2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spaciou... 

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$90,000
Provided courtesy of COLDWELL BANKER REALTY
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... 

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$89,900
Provided courtesy of REGAL REAL ESTATE LLC

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