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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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Royal Palm Village - Sun Communities

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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)

The Landings at Lake Henry - Sun Communities

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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 | 2 Baths | 1120 Sq. Ft.

339 ASHLEY DRIVE
Haines City, FL 33844

Site # 0339 Addr: 339 ASHLEY DRIVE

Deal of the Month- Double wide home for only $35,000!! 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 ...

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

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2 Beds | 2 Baths | 1152 Sq. Ft.

1701 W Commerce Ave Lot 192
Haines City, FL 33844

New Model deluxe kitchen 42" uppers and 7' long Island is a must see.

Welcome to Heartland Estates, where luxury meets energy efficiency in every corner of our homes. Picture yourself in a spacious open floor plan, surrounded by White Shaker cabinets, a large island perfect for entertaining, and top-tier Whirlpool stainless ...

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

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

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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 | 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 | 1248 Sq. Ft.

3000 US HWY 17/92 W LOT #549
Haines City, FL 33844

Site # 0549 Addr: 3000 US HWY 17/92 W LOT #549

Brand New Home - With Waterview!! Experience modern living in this beautifully designed 2-bedroom 2-bathroom manufactured home featuring a modern open layout with natural lighting, vinyl flooring throughout. The contemporary kitchen offers stainless-steel ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1248 Sq. Ft.

3000 US HWY 17/92 W LOT #550
Haines City, FL 33844

Site # 0550 Addr: 3000 US HWY 17/92 W LOT #550

New home with Waterview!! Experience modern living in this beautifully designed 2-bedroom 2-bathroom manufactured home featuring a modern open layout with vinyl flooring throughout. The contemporary kitchen offers additional storage space, stainless-steel ...

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

Heartland Estates

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2 Beds | 2 Baths | 1008 Sq. Ft.

1701 W Commerce Ave Lot 73
Haines City, FL 33844

New Plumbing & HWT 2024 - New AC unit 2022

Welcome to Heartland Estates, We are an active 55+ Lifestyle community. We are excited to present this spectacular, 2B2B home. This loved & cared for home is decorated beautifully. The updated kitchen has marble counter tops, New cabinets, Custom glass ...

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)

Ariana Village - Sun Communities

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2 Beds | 2 Baths | 1200 Sq. Ft.

1198 Ariana Village Boulevard
Lakeland, FL 33803

Site # 165 Addr: 1198 Ariana Village Boulevard

Beautifully Updated 2 Bedroom, 2 Bathroom Home with Bonus Room in a 55+ Community This move-in ready home offers the perfect blend of comfort, style, and low-maintenance living. The spacious open floor plan is ideal for entertaining or simply enjoying ...

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. Brand new A/C system installed January 2026. Featuring laminate flooring throughout main rooms and vinyl in the kitchen and bathroom, carpet in the lanai. This home comes fully furnished, ...

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

Heartland Estates

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2 Beds | 2 Baths | 988 Sq. Ft.

1701 W Commerce Ave Lot #88
Haines City, FL 33844

New Plumbing 2026 - New roof 2025

Welcome to Heartland Estates, A 55+ lifestyle community! Where your new home & active new lifestyle awaits you! We have an adorable home that is priced to sell. This 2B2B home is perfect for relaxation & entertainment alike.! Whether you are beginning ...

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

Ariana Village - Sun Communities

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2 Beds | 2 Baths | 1232 Sq. Ft.

1650 Kale Cove
Lakeland, FL 33803

Site # 038 Addr: 1650 Kale Cove

Welcome home to this beautifully maintained 2-bedroom, 2-bath residence located in an active 55+ community, tucked away on a quiet cul-de-sac for added privacy. The open floor plan offers a bright, welcoming feel and is perfect for both everyday living ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1056 Sq. Ft.

3000 US HWY 17/92 W, LOT #540
Haines City, FL 33844

Site # 0540 Addr: 3000 US HWY 17/92 W, LOT #540

Welcome to your home. This delightful 2-bedroom, 2-bathroom house offers comfortable living with all the conveniences you need right at your doorstep. This well-designed, partially furnished home is perfectly situated on the canal with beautiful water ...

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

Heartland Estates

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2 Beds | 2 Baths | 1300 Sq. Ft.

1701 W Commerce Ave Lot 159
Haines City, FL 33844

New plumbing & HWT 2023, Granite counter tops, Luxury vinyl floors & more!

Welcome to Heartland Estates an active and fun community! Where your new home awaits you! We have a stunning home to show you, This 2B2B 1300sq ft home comes fully furnished with leather Livingroom set, coffee bar, and beautiful decor throughout. This ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1120 Sq. Ft.

311 MAPLECREST DRIVE
Haines City, FL 33844

Site # 0311 Addr: 311 MAPLECREST DRIVE

This charming 2 bedroom, 2 bathroom home offers comfort and convenience with a modern touch. The updated kitchen features contemporary finishes and ample space for cooking and entertaining, while the spacious living room provides a welcoming area to ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 988 Sq. Ft.

1701 W Commerce Ave Lot #83
Haines City, FL 33844

New plumbing & HWT 2026 & New roof 2025!

Welcome to Heartland Estates, A 55+ lifestyle community! Where your new home & active new lifestyle awaits you! This priced to sell home has 2 bedrooms/2 bathrooms, New plumbing & HWT 2026, New roof in 2025, Comfort commode in primary bedroom, Open floor ...

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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