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Winter Haven, FL 55+ Retirement Communities and Homes

Winter Haven, Florida, is a charming city perfect for active adults 55+, known for its beautiful chain of lakes and relaxed lifestyle. With a warm climate and picturesque surroundings, Winter Haven offers plenty of outdoor activities, including boating, fishing, and watersports. Residents can explore the scenic beauty of Bok Tower Gardens, stroll along the historic downtown area, and enjoy local shops and restaurants. The city also boasts a vibrant arts and cultural scene, with theaters and music venues. Winter Haven provides a welcoming and engaging environment for a fulfilling retirement.

55+ communities, or active adult communities, are residential areas designed for individuals aged 55 and older. These communities offer a lifestyle tailored to older adults, featuring low-maintenance housing and various amenities such as fitness centers, swimming pools, and walking trails. Social interaction is encouraged through organized events, hobby groups, and recreational activities. Many communities provide additional services like healthcare facilities, transportation, and dining options. Located in desirable climates and scenic areas, they offer a serene and enjoyable living environment. The primary goal is to foster a vibrant, supportive atmosphere where residents can enjoy their retirement years with a focus on health, wellness, and social connections.

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Del Webb Lakewood Ranch

Del Webb Lakewood Ranch

Del Webb Lakewood Ranch

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6805 Del Webb Blvd
Lakewood Ranch, FL 34202

With over 150 miles of trails, a vibrant Main Street, and a wealth of outdoor recreational amenities, Lakewood Ranch is ideal for active retirement. Within this 17,500-acre master-planned community, Del Webb builds new home designs offering smart features that enhance the lifestyle you love.

Community Lifestyles: 55+ Communities, Active Retirement, Real Estate Homes and Land

Brookside Estates - M/I Homes, Inc.

Brookside Estates - M/I Homes, Inc.

Brookside Estates - M/I Homes, Inc.

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855 129th Street N.E.
Bradenton, FL 34212

Community Lifestyles: 55+ Communities, Active Retirement, Real Estate Homes and Land

Lake Placid

Lake Placid

Lake Placid

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1809 Citadel St
Lake Placid, FL 33573

Community Lifestyles: 55+ Communities, Active Retirement, Real Estate Homes and Land

Esplanade at Lakewood Ranch

Esplanade at Lakewood Ranch

Esplanade at Lakewood Ranch

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13015 Malachite Drive
Lakewood Ranch, FL 34211

This gated enclave of 1,250 detached villas and single-family homes is a recreational paradise. Esplanade brings a touch of Mediterranean to Southwest Florida with its regionally inspired architecture, lush landscaping, serene lakes and fabulous resort-style amenities. Condos from the mid $200s and homes from the $400s. Esplanade at Lakewood Ranch offers detached villas as well as single family homes alongside lush landscaping, serene lakes and plenty of amenities. Find your perfect place.

Community Lifestyles: 55+ Communities, Active Retirement, Real Estate Homes and Land

Indigo Lakewood Ranch

Indigo Lakewood Ranch

Indigo Lakewood Ranch

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12916 Deep Blue Place
Lakewood Ranch, FL 34211

Located in the heart of Lakewood Ranch in Bradenton, Florida, the gated community of Indigo by Neal Communities offers an active lifestyle neighborhood in a serene setting with countless recreation, dining and entertainment options close at hand. Choose from a fine selection of handsome single-family and twin villa homes that embrace Island, Spanish and Tuscan architectural design.

Community Lifestyles: 55+ Communities, Active Retirement, Real Estate Homes and Land

Southern Hills Plantation Club

Southern Hills Plantation Club

Southern Hills Plantation Club

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19850 Southern Hills Boulevard
Brooksville, FL 34601

Community Lifestyles: 55+ Communities, Active Retirement, Golf Course Living, Real Estate Homes and Land

Tuskawilla Trails

Tuskawilla Trails

Tuskawilla Trails

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1070 Cheyenne Trail
Winter Springs, FL 32708

Pets Allowed Pet Friendly

Tuskawilla Trails is beautiful. It's a family manufactured home community with 173 homes. The king-size ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Clover Leaf Farms - MyMH

Clover Leaf Farms - MyMH

Clover Leaf Farms - MyMH

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900 North Broad Street
Brooksville, FL 34601

Clover Leaf Farms is a 55+ community located in lovely Brooksville on Florida's west coast. Although ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Rental Homes

Lakewood Ranch

Lakewood Ranch

Lakewood Ranch

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6220 University Parkway
Sarasota, FL 34240

Award-winning Lakewood Ranch is a 8,500 acre master-planned community encompassing all aspects of residential and commercial development. Seven villages, offering a variety of lifestyles from townhomes to estate living, share dramatic landscapes with fore

Community Lifestyles: 55+ Communities, Active Retirement, Golf Course Living, Real Estate Homes and Land

The Woods at Sylvan Lea - M/I Homes, Inc.

The Woods at Sylvan Lea - M/I Homes, Inc.

The Woods at Sylvan Lea - M/I Homes, Inc.

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2076 Misty Sunrise Trail
Sarasota, FL 34240

Sylvan Lea means “wooded meadow” and this neighborhood more than lives up to this name. It’s where nature truly sets the stage for peaceful serenity in a lush wooded setting. There are beautiful tree canopies that are formed by oak, palm and pine trees. The neighborhood grounds are covered with ferns, dwarf jasmine and bromeliads. This private, tucked away community will become your oasis from the everyday hustle and bustle from the moment you step under the wooded canopy.

Community Lifestyles: 55+ Communities, Active Retirement, Oceanfront or Coastal (or near), Real Estate Homes and Land

Winter Haven, Florida, is a charming city perfect for active adults 55+, known for its beautiful chain of lakes and relaxed lifestyle. With a warm climate and picturesque surroundings, Winter Haven offers plenty of outdoor activities, including boating, fishing, and watersports. Residents can explore the scenic beauty of Bok Tower Gardens, stroll along the historic downtown area, and enjoy local shops and restaurants. The city also boasts a vibrant arts and cultural scene, with theaters and music venues. Winter Haven provides a welcoming and engaging environment for a fulfilling retirement.

55+ communities, or active adult communities, are residential areas designed for individuals aged 55 and older. These communities offer a lifestyle tailored to older adults, featuring low-maintenance housing and various amenities such as fitness centers, swimming pools, and walking trails. Social interaction is encouraged through organized events, hobby groups, and recreational activities. Many communities provide additional services like healthcare facilities, transportation, and dining options. Located in desirable climates and scenic areas, they offer a serene and enjoyable living environment. The primary goal is to foster a vibrant, supportive atmosphere where residents can enjoy their retirement years with a focus on health, wellness, and social connections.

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Featured Communities

Treasure Isle Estates

Treasure Isle Estates

141 Royal Palm Cir Port Orange FL 32127

WINTER ESCAPE OR YEAR-ROUND LIVING Treasure Isle Estates is a luxurious 55+ mobile home community conveniently located in Port Orange, Florida, ...

 

1 homes $26,900 - $26,900

141 Royal Palm Cir Port Orange, FL 32127

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Crystal River Village

Crystal River Village

1801 SE Hwy 19 Crystal River FL 34429

Crystal River Village, in Crystal River, Florida, is a perfect blend of location, home selection, services, amenities, price, climate, activities ...

 

8 homes $39,995 - $109,999

1801 SE Hwy 19 Crystal River, FL 34429

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Pelican Pier MHC

Pelican Pier MHC

6207 18th St. East Ellenton FL 34222

Discover brand-new 2-bedroom, 1.5-bath homes at Pelican Pier in Ellenton, Florida, offering modern design, efficient floor plans, and move-in-ready convenience ...

 

5 homes $10,000 - $29,999

6207 18th St. East Ellenton, FL 34222

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Timber Village

Timber Village

15130 Timber Village Rd Groveland FL 34736

Timber Village is a peaceful 55+ community located in Groveland, Florida. We’re surrounded by beautiful nature, wildlife and water. Take ...

 

15130 Timber Village Rd Groveland, FL 34736

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Fairlane Harbor

Fairlane Harbor

1500 Indian River Blvd Vero Beach FL 32960

Fairlane Harbor is a premier gated 55+ manufactured home community located in scenic Vero Beach, Florida, nestled right on the ...

 

2 homes $39,900 - $289,900

1500 Indian River Blvd Vero Beach, FL 32960

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Stonebrook - Sun Communities

Stonebrook - Sun Communities

8219 W. Charmaine Dr. Homosassa FL 34448

Nestled among Florida's most treasured natural wonders, Stonebrook in Homosassa, FLA, is a 55+ community that welcomes an active ...

 

6 homes $65,000 - $158,995

8219 W. Charmaine Dr. Homosassa, FL 34448

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Maplewood Estates

Maplewood Estates

1000 Chamberlain Dr Port Orange FL 32127

Maplewood Estates is a gated, resort-style 55+ manufactured home community located in Port Orange, Florida. Offering oversized home sites and ...

 

1000 Chamberlain Dr Port Orange, FL 32127

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Coach House

Coach House

4907 28th Ave E Palmetto FL 34221

Coach House is a gated, resort-style 55+ mobile home & RV community located in Palmetto, Florida, on Florida’s scenic Gulf ...

 

2 homes $15,000 - $150,000

4907 28th Ave E Palmetto, FL 34221

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