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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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Heartland Estates

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2 Beds | 2 Baths | 1144 Sq. Ft.

1701 W Commerce Ave Lot#119
Haines City, FL 33844

New roof 2018 - New washer & dryer 2025 - Low-E vinyl doubled paned windows

Welcome to Heartland Estates an active and fun community! Where your new home awaits you! We are excited to show you this partially furnished 2B2B. This inviting home welcomes you with a large driveway to park your golf cart or sit outside and enjoy ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 952 Sq. Ft.

3000 US HWY 17/92 W, LOT #243
Haines City, FL 33844

Site # 0243 Addr: 3000 US HWY 17/92 W, LOT #243

Welcome to your next home! This cozy and beautifully maintained 2-bedroom, 2-bath residence offers comfort, style, and convenience all on a desirable corner lot. Fully furnished and move-in ready, this home features a spacious open-concept layout with ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Waterfront Living (or near)

The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 784 Sq. Ft.

267 Dixie Dr.
Haines City, FL 33844

Site # 0267 Addr: 267 Dixie Dr.

Located in a welcoming 55+ community, this charming 2-bedroom, 2-bathroom mobile home offers 742 sq. ft. of easy, low-maintenance living. Built in 1992 and fully furnished, it features cozy carpeting throughout and includes all major appliances for your ...

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 1.5 Baths | 728 Sq. Ft.

59 BUTLER BLVD.
Haines City, FL 33844

Site # 0059 Addr: 59 BUTLER BLVD.

This well kept 2 bedroom 1.5 bath home is ready for a new owner. Featuring laminate flooring throughout main rooms and vinyl in the kitchen and bathroom, carpet in the lanai. This home comes fully furnished, you can move right in ! As an added feature ...

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 1 Baths | 672 Sq. Ft.

159 TARA LANE
Haines City, FL 33844

Site # 0159 Addr: 159 TARA LANE

This well maintained 2 bedroom, 1 bathroom home offers 672 square feet of comfortable living space in a desirable 55+ community. The property features a covered porch, ideal for outdoor enjoyment, and a carport providing convenient covered parking. The ...

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

Heartland Estates

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3 Beds | 2 Baths | 1289 Sq. Ft.

1701 W. Commerce Ave. Lot 107
Haines City, FL 33844

2024 Skyline Champion Deluxe Island Kitchen open plan

Welcome to our vibrant 55+ community at Heartland Estates! Step into this modern three-bedroom home with energy-efficient low e-glass windows throughout. Whirlpool premium stainless steel appliances and 42" soft grey cabinetry. The open floor plan features ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1254 Sq. Ft.

1701 W. Commerce Ave. Lot 263
Haines City, FL 33844

Truly move in ready!!

Welcome to Heartland Estates, where an inviting & active community awaits you! We are excited to present this welcoming & bright 2B2B home that perfectly embodies the atmosphere of relaxation & tranquil living. Imagine your day filled with fun activities ...

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

Heartland Estates

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2 Beds | 2 Baths | 1080 Sq. Ft.

1701 W. Commerce Ave. Lot 101
Haines City, FL 33844

Truly ready to move in! Many updates.

Welcome to Heartland Estates, a beautifully secluded and vibrant community where tranquility meets engagement. Nestled on a quiet street, this home offers a perfect blend of comfort and style, designed for those seeking an active yet peaceful lifestyle. ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1100 Sq. Ft.

1701 W Commerce Ave Lot 190
Haines City, FL 33844

Just steps from Lake, pool & clubhouse

Welcome to Heartland Estates, Where community, new friends & relaxation awaits you. This beautiful home is conveniently located around the corner from our clubhouse, heated pool and Lake Hester. As you come home, picture yourself in a spacious -open ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1144 Sq. Ft.

1701 W Commerce Ave #126
Haines City, FL 33844

New roof, carport & Plumbing. All in 2025 New AC 2024

Welcome to Heartland Estates! An active, beautiful and inviting community! Where your new home awaits you! We are excited to show you this fully furnished 2B2B home that embraces the ambiance of relaxation & retirement. Whether you are beginning your ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1254 Sq. Ft.

1701 W Commerce Ave Lot #253
Haines City, FL 33844

New roof 2025 - Move-in ready!

Welcome to Heartland Estates, where a friendly & active community awaits you! We are excited to present this inviting & spacious 2B2B home. Many upgrades have been done for you, Making tis a move-in ready home. This spacious home is inviting to all ...

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 864 Sq. Ft.

336 ASHLEY DRIVE
Haines City, FL 33844

Site # 0336 Addr: 336 ASHLEY DRIVE

This charming 2-bedroom, 2 bath home is located in the desirable 55+ community. The home features an extended driveway, a brand new carport, and two screened in porches perfect for enjoying Florida s sunshine. Inside, you ll find a bright, open layout ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 784 Sq. Ft.

263 DIXIE DRIVE
Haines City, FL 33844

Site # 0263 Addr: 263 DIXIE DRIVE

Welcome to this beautifully updated home featuring hardwood flooring throughout the main living areas and a spacious, open layout. The bright enclosed porch offers the perfect spot to relax and enjoy natural light all year round. The covered back patio ...

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 1.5 Baths | 770 Sq. Ft.

134 MAGNOLIA LANE
Haines City, FL 33844

Site # 0134 Addr: 134 MAGNOLIA LANE

Welcome to this beautifully updated 2 bedroom, 1.5 bathroom home located in a highly sought after 55+ community. This charming residence offers modern updates and timeless comfort, featuring gleaming hardwood flooring throughout for a warm and inviting ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1120 Sq. Ft.

339 ASHLEY DRIVE
Haines City, FL 33844

Site # 0339 Addr: 339 ASHLEY DRIVE

This beautifully maintained home offers an open floor plan filled with natural light, highlighted by skylights in both the kitchen and bathroom. Important updates include a new roof installed in 2022 and a new carport added the same year, providing durability ...

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

Royal Palm Village - Sun Communities

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3 Beds | 2 Baths | 1456 Sq. Ft.

3000 US HWY 17/92 W, LOT #103
Haines City, FL 33844

Site # 0103 Addr: 3000 US HWY 17/92 W, LOT #103

Motivated Sellers ! This beautifully maintained 3-bedroom, 2-bath home combines comfort, space, and functionality in every corner. Each bedroom offers generous dimensions with spacious closets featuring extra shelving. The open, well-equipped kitchen, ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Waterfront Living (or near)

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 900 Sq. Ft.

1701 W Commerce Ave Lot 141
Haines City, FL 33844

New Plumbing 2025 - Handy man special

Welcome to our 55+ community! An active, beautiful and inviting 55+ lifestyle community! Where your new home awaits you! We are excited to show you this priced to sell; 2B2B home that is awaiting you! Whether you are beginning your day with a cup of ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1012 Sq. Ft.

3000 US HWY 17/92 W LOT #564
Haines City, FL 33844

Site # 0564 Addr: 3000 US HWY 17/92 W LOT #564

New 2-bedroom, 2-bath manufactured home with a modern open layout. Features include vinyl flooring throughout, a farmhouse-style stainless steel kitchen sink, and black matte faucets and fixtures for a sleek, contemporary look. Please note: photos are ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Waterfront Living (or near)

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1680 Sq. Ft.

3000 US HWY 17/92 W LOT #633
Haines City, FL 33844

Site # 0633 Addr: 3000 US HWY 17/92 W LOT #633

Welcome to this charming and fully furnished 2-bedroom, 2-bathroom manufactured home with a den perfect for a home office, guest space, or hobby room. Move-in Ready! This cozy abode features a convenient 1-car garage, ideal for storing all your outdoor ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Waterfront Living (or near)

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1352 Sq. Ft.

1701 W Commerce Ave Lot 128
Haines City, FL 33844

New roof & AC 2024 - Many more updates

Welcome to Heartland Estates an active and fun community! Where your new home awaits you! We have a beautiful home to share with you, This 2 bedroom/ 2 bathroom 1352 Square foot home is move-in ready! This inviting home offers peace of mind with all ...

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

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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