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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 | 962 Sq. Ft.

1701 W Commerce Ave Lot # 123
Haines City, FL 33844

Beautifully updated home in quiet neighborhood

Beautifully Upgraded Home in Quiet & active 55+ community. Welcome to your dream home! This beautifully renovated residence is designed with your comfort and style in mind, ensuring a seamless transition into a vibrant community. With a newly installed ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 960 Sq. Ft.

3000 US HWY 17/92 W, LOT #123
Haines City, FL 33844

Site # 0123 Addr: 3000 US HWY 17/92 W, LOT #123

Discover your dream home by the serene preserve area! This stunning 2-bedroom, 2-bathroom residence offers a perfect blend of comfort and style. Enjoy the beautiful Florida weather year-round in the spacious enclosed porch. The kitchen features chic ...

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

Lake Hammock Village

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2 Beds | 2 Baths | 1252 Sq. Ft.

74 Silver Crest Dr.
Haines City, FL 33844

BRAND NEW 2/2 +DEN MODEL HOME

Brand New Home!!!! Open Bright and Airy 2BR / 2Bath plus Den Split-Plan Home . This New Home Features: Open, Spacious Living Areas, 8 Foot Ceilings Throughout. Kitchen has Morning Room along with upgraded S/S Appliances. Spacious Primary Bedroom with ...

Community Lifestyles: 55+ Communities, Active Retirement

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

Lake Hammock Village

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3 Beds | 2 Baths | 1456 Sq. Ft.

199 Glen Este Blvd.
Haines City, FL 33844

BRAND NEW 3/2 MODEL HOME

Brand New Open Bright and Airy 3BR / 2Bath Split-Plan Home Available NOW! This New Home Features: Open Spacious Living Areas. Kitchen has Large Island with Seating and Lots of Storage, All Upgrade Appliances, and a Walk-In Pantry. Spacious Master Bedroom ...

Community Lifestyles: 55+ Communities, Active Retirement

Heartland Estates

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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 | 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

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

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

Heartland Estates

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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

The Landings at Lake Henry - Sun Communities

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2 Beds | 1.5 Baths | 728 Sq. Ft.

22 O`HARA DRIVE
Haines City, FL 33844

Site # 0022 Addr: 22 O`HARA DRIVE

This well kept 2-bedroom, 1.5 bath home is located in a peaceful 55+ community and offers 728 square feet of comfortable living space. The cozy interior features carpeted floors, a bright and open living area, and a functional kitchen with plenty of ...

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

Heartland Estates

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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

Heartland Estates

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2 Beds | 2 Baths | 1056 Sq. Ft.

1701 W Commerce Ave Lot 79
Haines City, FL 33844

Charming home with many updates

Beautiful move-in ready home located in Heartland Estates; an inviting & active 55+ community. This home has several updates, A new roof, carport, HWT & plumbing all done in 2024.This ensures a simple & stress free transition to your new retirement lifestyle. ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1012 Sq. Ft.

3000 US HWY 17/92 W, LOT #2
Haines City, FL 33844

Site # 0002 Addr: 3000 US HWY 17/92 W, LOT #2

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)

The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 728 Sq. Ft.

100 WILKES DRIVE
Haines City, FL 33844

Site # 0100 Addr: 100 WILKES DRIVE

Newly listed this home is a MUST SEE. This well maintained home comes furnished and ready to move in. The large living room opens to the dining area and open kitchen. The spacious open kitchen has lots of storage space. Laminate floors throughout home. ...

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

Lake Hammock Village

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2 Beds | 2 Baths | 1828 Sq. Ft.

34 Sargent St.
Haines City, FL 33844

EVERYTHING NEW 2/2+DEN

Lovely 2BR / 2BATH Plus Den is All New. This Great Home Features: Completely New Kitchen and Both Baths. New S/S Appliances. New Interior Paint and Laminate Flooring Throughout. Great for Entertaining, Home Features large Open Spacious living Areas, ...

Community Lifestyles: 55+ Communities, Active Retirement

Heartland Estates

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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

Lake Hammock Village

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1376 Sq. Ft.

24 Silver Crest Dr.
Haines City, FL 33844

TURN KEY MOVE-IN READY 2/2 SPLIT PLAN

MUST SEE. Turn-key, Move-In Ready 2BR/2BATH Split Plan Home. This Great Home Features: Kitchen has Granite Counter Tops, Island Bar with Storage. Laminate Floors Throughout. Home has New Roof, New Thermo-Payne Windows, and a New HVAC Unit. Master Bath ...

Community Lifestyles: 55+ Communities, Active Retirement

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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