David Shippey
863.521.4517

Retirement Homes for Sale in Winter Haven FL


Winter Haven FL Real Estate featuring Retirement Homes are listed below. These Retirement 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 Retirement homes for sale, please call 863-521-4517 or just click the "Schedule a Showing" or "Request More Info" button on any property detail pages.

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Displaying results 91-100 of 150
57 Photos 3832 Traditions Boulevard Winter Haven, FL 33884

3832 Traditions Boulevard
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4932254 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Welcome to this lovely well-maintained home with a tranquil water view, located in the active community Traditions. Home is a split floor plan, wit... 

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$310,000
Reduced -$5,000
Provided courtesy of CENTURY 21 MYERS REALTY
4 Photos 1700 6th Street UNIT C7 Winter Haven, FL 33881

1700 6th Street UNIT C7
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo
Residential

MLS# P4932186 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 640 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Winter Haven Harbour Apts Condo

Ground floor unit overlooking the pool and recreation area. This is a smoke free and animal free neighborhood. 

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$82,500
Provided courtesy of CHOICE PROPERTIES OF CENT FL
26 Photos 191 Sweet Circle Winter Haven, FL 33884

191 Sweet Circle
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# P4931913 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1176 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

LOOK NO FURTHER!!! 2Bed/2Bath located in a fabulous 55+ gated CO-OP community in Winter Haven. The community provides a lifestyle tailored to activ... 

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$67,000
Reduced -$8,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
60 Photos 4321 Cherrywood Street Winter Haven, FL 33880

4321 Cherrywood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4931788 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1488 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the... 

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$129,900
Provided courtesy of COLDWELL BANKER REALTY
17 Photos 1521 Oakview Circle Winter Haven, FL 33880

1521 Oakview Circle
Winter Haven, FL 33880
Oakview
Residential

MLS# P4931725 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1186 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakview

Discover 55+ Living in this renovated Oakview villa! Welcome to Oakview, a charming 48-unit community perfectly situated near Wal-Mart, Publix, res... 

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$219,900
Reduced -$4,099
Provided courtesy of THE STONES REAL ESTATE FIRM
60 Photos 2505 Salzburg Loop Winter Haven, FL 33884

2505 Salzburg Loop
Winter Haven, FL 33884
Vienna Square Ph 01
Residential

MLS# P4931555 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 2062 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 01

Welcome to Vienna Square in Winter Haven located in Central Florida. This 55+ community is a beautiful community and offers their homeowners many a... 

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$319,000
Reduced -$19,300
Provided courtesy of XCELLENCE REALTY, INC
5 Photos 400 El Camino Drive UNIT #223 Winter Haven, FL 33884

400 El Camino Drive UNIT #223
Winter Haven, FL 33884
Orchid Spgs Vill 400 San Miguel
Residential

MLS# P4930895 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 850 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Spgs Vill 400 San Miguel

REDUCED!!! SELLER SAYS ""SELL"" THIS ONE BEDROOM CONDO AT ORCHID SPRINGS VILLAGE, A TRANQUIL 55+ COMMUNITY, HAS GREAT VIEWS OF MATURE LANDSCAPING -... 

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$74,900
Reduced -$10,100
Provided courtesy of THE K TEAM REAL ESTATE SERVICES LLC
95 Photos 4568 Back Nine Drive Winter Haven, FL 33884

4568 Back Nine Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4930744 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2043 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

You dont want to miss out on this one-owner, three-bedroom, two-bath SEBASTIAN floor plan home that is filled with special features. The fully paid... 

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$360,000
Provided courtesy of A+ REALTY LLC
21 Photos 1776 6th Street UNIT #303 Winter Haven, FL 33881

1776 6th Street UNIT #303
Winter Haven, FL 33881
Lakeridge Condo
Residential

MLS# P4929979 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1347 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeridge Condo

Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake ... 

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$130,000
Provided courtesy of CENTURY 21 MYERS REALTY
63 Photos 4577 Back Nine Drive Winter Haven, FL 33884

4577 Back Nine Drive
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4929580 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1918 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

This home features 3 bedrooms and 2 full baths and is located in Lake Ashton, a Florida Retirement 55+ community in sunny Central Florida. Offering... 

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$375,900
Provided courtesy of LAKE ASHTON REALTY INC.

Broker Reciprocity The information being provided by © 2025 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 REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, 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 07-21-2025 11:53 AM EST.

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The retirement homes above are brought to you by David Shippey REALTOR®.

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