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 11-20 of 132
44 Photos 6775 Brentwood Drive Winter Haven, FL 33881

6775 Brentwood Drive
Winter Haven, FL 33881
Lake N Golf Estates
Residential

MLS# S5146696 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1320 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates

One or more photo(s) has been virtually staged. Welcome to 6775 Brentwood Dr NE, located in the desirable no pet community of Lake N Golf Estates, ... 

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$132,500
Reduced -$4,400
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
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
54 Photos 4019 Carteret Drive Winter Haven, FL 33884

4019 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# S5145776 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1719 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

One or more photo(s) has been virtually staged. Welcome to this beautifully maintained residence located in the lakefront community of Traditions, ... 

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$269,999
Reduced -$4,901
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
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
42 Photos 6825 S Lake Henry Drive Winter Haven, FL 33881

6825 S Lake Henry Drive
Winter Haven, FL 33881
Lucerne Park Fruit Assn
Residential

MLS# S5143698 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1790 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lucerne Park Fruit Assn

One or more photo(s) has been virtually staged. Enjoy true Florida lakefront living in this spacious 2-bedroom, 2-bath home offering almost 1800 sq... 

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$239,000
Reduced -$10,900
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
33 Photos 400 El Camino Drive UNIT #210 Winter Haven, FL 33884

400 El Camino Drive UNIT #210
Winter Haven, FL 33884
Orchid Spgs Vill 400 San Miguel
Residential

MLS# S5142500 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1666 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Spgs Vill 400 San Miguel

Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the... 

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$130,000
Reduced -$5,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
43 Photos 4420 Limewood Street Winter Haven, FL 33880

4420 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# S5142224 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 864 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Welcome home to 4420 Limewood St in Winter Haven, located in the desirable 55+ co-op community of Oakwood Estatesa neighborhood known for active li... 

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$112,000
Reduced -$5,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
16 Photos 100 El Camino Drive UNIT #111 Winter Haven, FL 33884

100 El Camino Drive UNIT #111
Winter Haven, FL 33884
Orchid Spgs Vill 100 Condo
Residential

MLS# S5141094 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 931 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Spgs Vill 100 Condo

Owner motivated and ready to negotiate WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located... 

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$65,000
Reduced -$6,000
Provided courtesy of LPT REALTY, LLC
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
52 Photos 6044 Grand Oaks Drive Winter Haven, FL 33884

6044 Grand Oaks Drive
Winter Haven, FL 33884
Garden Grove Oaks
Residential

MLS# S5126925 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1248 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove Oaks

Welcome to 6044 Grand Oaks Dr SE in Winter Haven, a beautifully updated waterfront home in the desirable 55+ community of Garden Grove Oaks, where ... 

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$169,900
Reduced -$15,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS

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