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
46 Photos 6643 Westchester Drive Winter Haven, FL 33881

6643 Westchester Drive
Winter Haven, FL 33881
Lake N Golf Estates Add
Residential

MLS# L4960802 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1456 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates Add

Welcome to easy Florida lake view living in this beautifully updated 2-bedroom, 2-bath home located in a friendly 55+ no pet community on the shore... 

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$185,000
Provided courtesy of COLDWELL BANKER REALTY
52 Photos 6086 Southern Oaks Drive Winter Haven, FL 33884

6086 Southern Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# L4959284 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1040 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Welcome to 6086 Southern Oaks Drive SE, a beautifully updated and well- maintained, move in ready manufactured home located in the highly sought af... 

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$185,000
Provided courtesy of LOCKHART & ASSOCIATES INC
17 Photos 1224 Vienna Square Drive Winter Haven, FL 33884

1224 Vienna Square Drive
Winter Haven, FL 33884
Vienna Square Duplex
Residential

MLS# P4934564 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1118 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Duplex

ANOTHER PRICE IMPROVEMENT. ONCE IN A LIFETIME OPPORTUNITY! CAN'T BEAT THIS PRICE IN THIS COMMUNITY!!! This is a charming 2-bedroom, 2-bath home in ... 

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$185,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
28 Photos 6450 Hollyberry Lane Winter Haven, FL 33881

6450 Hollyberry Lane
Winter Haven, FL 33881
Brookhaven Village
Residential

MLS# L4960650 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1144 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village

One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Villagea highly sought-after 55+ community where you ... 

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$188,500
Reduced -$1,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
20 Photos 6394 Lolly Bay Loop Winter Haven, FL 33881

6394 Lolly Bay Loop
Winter Haven, FL 33881
Brookhaven Village Second Add
Residential

MLS# L4958069 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1620 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village Second Add

Located in the 55+ community of Brookhaven Village, this fee-simple manufactured home offers 1,620 square feet of living space with a functional la... 

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$189,900
Provided courtesy of COLDWELL BANKER REALTY
56 Photos 4925 Cypress Gardens Road UNIT #100 Winter Haven, FL 33884

4925 Cypress Gardens Road UNIT #100
Winter Haven, FL 33884
Doves Rest Add
Residential

MLS# P4938418 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1008 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Doves Rest Add

Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Ai... 

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$195,000
Provided courtesy of COLDWELL BANKER REALTY
55 Photos
Open House: Sat Jun 20th, 11:00am - 1:00pm
6346 Bayberry Blvd Ne Winter Haven, FL 33881

6346 Bayberry Blvd Ne
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# P4936920 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1440 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

PRICE IMPROVEMENT & HOME WARRANTY INCLUDED! Now offered at an even better value, this beautifully maintained home in Brookhavens desirable 55+ comm... 

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$195,000
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

Virtually Staged. Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community ready for a new owner. Single-level, move-in ready ho... 

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$199,900
Provided courtesy of KELLER WILLIAMS REALTY SMART
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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$205,000
Reduced -$10,000
Provided courtesy of GREEN STAR REALTY, INC.
44 Photos 1590 Vienna Square Drive Winter Haven, FL 33884

1590 Vienna Square Drive
Winter Haven, FL 33884
Vienna Square Ph 2a
Residential

MLS# O6406908 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1231 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 2a

Welcome to Vienna Square a vibrant, beautifully maintained 55+ gated community where resort-style living meets true low-maintenance comfort. This c... 

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$210,000
Provided courtesy of RE/MAX PRIME PROPERTIES

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