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 121-130 of 130
70 Photos 2825 Attwater Loop Winter Haven, FL 33884

2825 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# S5152439 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Welcome to 2825 Attwater Drive, a beautifully maintained villa in the sought after gated 55+ community of Traditions at Lake Ruby, where low mainte... 

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$199,999
Provided courtesy of LPT REALTY, LLC
53 Photos 6235 Knotty Pine Drive Winter Haven, FL 33884

6235 Knotty Pine Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# P4939218 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1080 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

CUTE AND COZY 2 BR/2 BA HOME IN GARDEN GROVE OAKS 55+ COMMUNITY! This one-owner home is in one of Winter Haven`s most sought-after 55+ communities ... 

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$159,900
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
70 Photos 6209 Pinehurst Loop Winter Haven, FL 33884

6209 Pinehurst Loop
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# P4939200 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2526 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

Modern Elegance! 6209 Pinehurst Loop Winter Haven, Florida 33884. Built in 2021, this custom designed home is located in Lake Ashton, one of Centra... 

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$589,000
Provided courtesy of LAKE ASHTON REALTY INC.
20 Photos 5811 Marsh Landing Drive Winter Haven, FL 33881

5811 Marsh Landing Drive
Winter Haven, FL 33881
Lakeside Landings Ph 01
Residential

MLS# O6423020 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1873 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeside Landings Ph 01

Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bath home tucked inside THE PRESERVE, a quiet and intimate 55+ gated enclave within the h... 

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$280,000
Provided courtesy of MARK SPAIN REAL ESTATE
34 Photos 6666 Briarhill Drive Winter Haven, FL 33881

6666 Briarhill Drive
Winter Haven, FL 33881
Lake N Golf Estates Add
Residential

MLS# S5153400 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1144 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates Add

Welcome home to this beautifully maintained residence in the highly sought-after Lake-n-Golf Estates, where comfort, convenience, and an active lif... 

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$140,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III
29 Photos 333 Lake Howard Drive UNIT 211B Winter Haven, FL 33880

333 Lake Howard Drive UNIT 211B
Winter Haven, FL 33880
Imperial Harbours Ph 01
Residential

MLS# L4963297 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1218 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harbours Ph 01

Remodeled and updated 2nd floor condo with picturesque views of the pool and lush landscaping. This 3 bedroom unit is ready for immediate occupancy... 

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$149,900
Provided courtesy of LOCKHART & ASSOCIATES INC
39 Photos 333 Lake Howard Dr Nw UNIT 102D Winter Haven, FL 33880

333 Lake Howard Dr Nw UNIT 102D
Winter Haven, FL 33880
Imperial Harbours
Residential

MLS# P4939253 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harbours

FIRST FLOOR BEAUTY! This move-in-ready 2 bedroom 2 bath condo is just what you`ve been waiting to find. 2025 was a big year with loads of quality u... 

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$110,000
Provided courtesy of CENTURY 21 WATSON & MYERS REALTY
46 Photos 128 Lake Hazel Drive Winter Haven, FL 33884

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

MLS# P4939283 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1680 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

Welcome to Orange Manor West in desirable southeast Winter Haven. This spacious 2-bedroom, 2-bathroom home offers comfort and functionality in a qu... 

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$59,999
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
35 Photos 1776 6th Street UNIT #807 Winter Haven, FL 33881

1776 6th Street UNIT #807
Winter Haven, FL 33881
Lakeridge Condo
Residential

MLS# L4963444 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1347 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeridge Condo

NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room wit... 

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$162,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
23 Photos 1700 6th Street UNIT A38 Winter Haven, FL 33881

1700 6th Street UNIT A38
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# L4963441 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 840 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

Virtually Staged. Perched on the third floor, Unit A38 at Winter Haven Condominiums offers the perfect blend of privacy, convenience, and beautiful... 

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$78,800
Provided courtesy of S & D REAL ESTATE SERVICE LLC

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