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 1-10 of 133
21 Photos 17 Kendra Court Winter Haven, FL 33880

17 Kendra Court
Winter Haven, FL 33880
Brandy Chase Village A Rep
Residential

MLS# B4901832 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 960 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Brandy Chase Village A Rep

Just reduced approx. $30,000 below appraised value to allow for remodeling! This 2 Bedroom, 2 Bath home is located in Brandy Chase Village, a well-... 

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$115,000
Reduced -$10,000
Provided courtesy of KLINE REAL ESTATE SERVICES
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
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
51 Photos 6308 Bayberry Boulevard Winter Haven, FL 33881

6308 Bayberry Boulevard
Winter Haven, FL 33881
Brookhaven Village
Residential

MLS# P4933148 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1152 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village

LOW-COST YEAR AROUND LIVING! VERY WELL MAINTAINED! Fully Furnished everything stays! Pet Friendly lot. Gorgeous updating, Very Clean & Move-In read... 

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$155,700
Reduced -$4,000
Provided courtesy of COLDWELL BANKER REALTY
11 Photos 6433 Jacaranda Avenue Winter Haven, FL 33881

6433 Jacaranda Avenue
Winter Haven, FL 33881
Brookhaven Village
Residential

MLS# S5144807 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 912 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village

Significant price improvement and a highly motivated seller make this an exceptional opportunity in the sought-after 55+ Brookhaven Village communi... 

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$145,000
Increase +$5,100
Provided courtesy of LA ROSA REALTY ORLANDO LLC
38 Photos 6443 Hollyberry Lane Winter Haven, FL 33881

6443 Hollyberry Lane
Winter Haven, FL 33881
Brookhaven Village
Residential

MLS# L4962398 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 989 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village

Best Deal in Polk County!!!! Highly desirable 55+ Brookehaven Village community! This charming 2-bedroom, 2-bathroom manufactured home offers comfo... 

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$94,999
Provided courtesy of LIVE FLORIDA REALTY
13 Photos 6332 Bayberry Boulevard Winter Haven, FL 33881

6332 Bayberry Boulevard
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# S5146261 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1012 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

This home located in the desirable Brookhaven Village community in Winter Haven. This property offers a comfortable layout with spacious living are... 

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$106,000
Provided courtesy of R&J REALTY AND PROPERTY MANAGEMENT LLC
38 Photos 6473 Peppertree Path Winter Haven, FL 33881

6473 Peppertree Path
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# P4938365 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1107 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

EASY TO SEE, SCHEDULE YOU'RE VIEWING NOW! NO LOT RENT HERE....YOU OWN IT! OFFERED PARTIALLY FURNISHED, KITCHEN APPLIANCES AND INSIDE LAUNDRY WASHER... 

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$146,000
Provided courtesy of COLDWELL BANKER REALTY
42 Photos 6518 Raintree Lane Winter Haven, FL 33881

6518 Raintree Lane
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# S5136893 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1525 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

Welcome to this beautifully maintained home offering 2 bedrooms and 2 bathrooms plus an office in the desirable 55+ community of Brookhaven Village... 

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$165,000
Reduced -$5,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
49 Photos 6561 Chinaberry Dr Ne Winter Haven, FL 33881

6561 Chinaberry Dr Ne
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# L4960831 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1596 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desira... 

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$155,900
Provided courtesy of CROSBY & ASSOCIATES, INC.

Broker Reciprocity The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 06-06-2026 9:39 AM EST.

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