David Shippey
863.521.4517

55 Plus Homes for Sale in 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 Showing" or "Request More Info" button on any property detail pages.

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Displaying results 91-100 of 150
18 Photos 333 Lake Howard Drive UNIT 201A Winter Haven, FL 33880

333 Lake Howard Drive UNIT 201A
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# O6322591 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1114 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

This 2 bedroom 2 bath condo is located in the Imperial Harbour 55+ complex on Lake Howard. The unit has a great view of the lake from the master be... 

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$83,000
Provided courtesy of FAMILY REALTY
71 Photos 1394 Oakmont Drive Winter Haven, FL 33884

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

MLS# L4952569 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2606 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2

Back on market! Buyer(s) contingency fell through. Discover an exceptional home for sale in the beautiful Lake Ashton Golf course community, which ... 

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$565,000
Provided courtesy of AGILE GROUP REALTY
43 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

Fully Furnished* Gorgeous updating, Very Clean & Move-In ready! Brookhaven Village in the heart of Central Florida is a well-established and mainta... 

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$167,300
Provided courtesy of COLDWELL BANKER REALTY
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
52 Photos 1644 Linz Ct Winter Haven, FL 33884

1644 Linz Ct
Winter Haven, FL 33884
Vienna Square and the Villas At Vienna S
Residential

MLS# P4932813 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1329 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square and the Villas At Vienna S

CUSTOM CUTIE! EXTERIOR PAINT, ROOF, IRRIGATION WATER, YARD MOWING, SHRUB TRIMMING, and SPECTRUM Internet/TV package is included in the reasonable m... 

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$249,900
Reduced -$3,100
Provided courtesy of CENTURY 21 WATSON & MYERS REALTY
29 Photos 148 Sweet Circle Winter Haven, FL 33884

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

MLS# P4934464 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1248 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

Fully furnished 2 bedroom/2 bath home in Orange Manor West. Enjoy your mornings/evenings on your spacious, enclosed lanai. Located in Southeast Win... 

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$89,900
Provided courtesy of BHHS FLORIDA PROPERTIES GROUP
63 Photos 2769 Attwater Loop Winter Haven, FL 33884

2769 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# S5124391 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Welcome to 2769 Attwater Loop in Winter Haven **move-in ready**, beautifully maintained villa with a flex room and covered, screened lanai offering... 

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$234,000
Reduced -$5,000
Provided courtesy of JASON MITCHELL REAL ESTATE FLO
44 Photos 3007 Caneel St Winter Haven, FL 33884

3007 Caneel St
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# O6310659 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Located in a 55+ community, this home offers a functional layout with plenty of room to personalize. Both bedrooms are generously sized, providing ... 

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$223,000
Reduced -$2,000
Provided courtesy of KELLER WILLIAMS REALTY AT THE PARKS
35 Photos 6515 Raintree Lane Winter Haven, FL 33881

6515 Raintree Lane
Winter Haven, FL 33881
Brookhaven Village First Add
Residential

MLS# P4934174 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1620 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Brookhaven Village First Add

Wonderful 2 bedroom/2 bath FURNISHED home located in Winter Haven's Brookhaven Village, an established 55+ community with a community pool, clubhou... 

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$148,000
Reduced -$6,000
Provided courtesy of CENTURY 21 MYERS REALTY
47 Photos 2980 Dayton Drive Winter Haven, FL 33884

2980 Dayton Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4934717 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2302 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Experience the best of Floridas 55+ lifestyle at 2980 Dayton Drive. A refined offering set on a large corner lot in Traditions at Lake Ruby, one of... 

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$416,900
Reduced -$8,100
Provided courtesy of NEXTHOME NORRIS & COMPANY REALTY

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 07-22-2025 9:25 AM EST.

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