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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

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1326 Sq. Ft.

1701 W Commerce Ave Lot # 160
Haines City, FL 33844

New plumbing & HWT 2026 - New AC 2025 - New roof 2023

Welcome to Heartland Estates, A warm, welcoming & well-established 55+ community. We are beautifully secluded atop one of the highest points in Polk County-Second only to Bok Towers. This meticulously loved & cared for home has 2 bedrooms & 2 bathrooms. ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1624 Sq. Ft.

3000 US HWY 17/92 W LOT #643
Haines City, FL 33844

Site # 0643 Addr: 3000 US HWY 17/92 W LOT #643

Welcome to this well-maintained 2007 home offering the perfect combination of comfort, space, and convenience. Inside, you ll find an inviting open living and dining area, a versatile office/den, and a fully equipped kitchen with all appliances included. ...

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

Blue Heron Bay

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2 Beds | 2 Baths

183 Osprey Dr.
Haines City, FL 33844

This charming 864 square feet manufactured home, built by Homes of Merit, offers a functional living space featuring 2 bedrooms and 2 bathrooms. Inside, you’ll find a cozy living room and dining area perfect for relaxing and entertaining. The master ...

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 924 Sq. Ft.

77 WILKES DRIVE
Haines City, FL 33844

Site # 0077 Addr: 77 WILKES DRIVE

Step into this charming 2 bedroom 2 bathroom home. This home offers a bright, open layout with modern finishes throughout, the spacious kitchen features ample cabinetry, generous counter space and a convenient breakfast bar that flows seamlessly into ...

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)

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1066 Sq. Ft.

3000 US HWY 17/92 W, LOT #299
Haines City, FL 33844

Site # 0299 Addr: 3000 US HWY 17/92 W, LOT #299

Introducing your next home sweet home! This charming abode features 2 bedrooms, 2 bathrooms, plus a cozy den, offering a comfortable and versatile living space. Prepare to be impressed by the stylish upgrades throughout this home. The open-concept design ...

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 | 1760 Sq. Ft.

3000 US HWY 17/92 W LOT #652
Haines City, FL 33844

Site # 0652 Addr: 3000 US HWY 17/92 W LOT #652

Rare opportunity in Royal Palm Village! This enormous 2008 Skyline triple-wide offers an impressive 44x40 layout with an oversize garage, a unique find in the community. Inside, you'll find expansive living spaces, high ceilings, abundant natural light, ...

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

Blue Heron Bay

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3 Beds | 2 Baths

281 Crane Ln.
Haines City, FL 33844

Welcome to Blue Heron Bay! This beautiful 2026 manufactured home offers 1,456 square feet of thoughtfully designed living space with 3 bedrooms and 2 bathrooms, making it the perfect place to call home. Step inside to discover a spacious open-concept ...

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

Lake Hammock Village

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3 Beds | 2 Baths | 1540 Sq. Ft.

177 Glen Este Blvd.
Haines City, FL 33844

TURN KEY MOVE IN READY 3/2 SPLIT PLAN IS A MUST SEE

Turn Key, Move-In Ready, Excellent Condition 3BR / 2Bath Split- Plan Home is Priced to Sell Now. Completely Furnished And Accessorized, all you need are your clothes and toothbrush! This Great Home Features: Laminate Flooring Throughout, Ceramic Floors ...

Community Lifestyles: 55+ Communities, Active Retirement

Heartland Estates

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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

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

Heartland Estates

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3 Beds | 2 Baths | 1400 Sq. Ft.

1701 W Commerce Ave Lot 81
Haines City, FL 33844

Beautifully Furnished Corner Lot Home - $89,000

3 Bedrooms - 2 Bathrooms - 1,610 Sq. Ft. Under Air Discover comfortable Florida living in this inviting 2003 Jacobson home, ideally situated on a corner lot in Heartland Estates, an active 55+ community. Offered fully furnished, with all furnishings ...

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

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1152 Sq. Ft.

1701 W Commerce Ave Lot 192
Haines City, FL 33844

New Model - 27 month Rent Special $499, $599, $699

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1024 Sq. Ft.

3000 US HWY 17/91 W Lot# 0200
Haines City, FL 33844

Site # 0200 Addr: 3000 US HWY 17/91 W Lot# 0200

Welcome home to this beautifully maintained manufactured home, located inside 55+ community. Offering comfort, style, and modern convenience. This inviting 2-bedroom, 2-bathroom residence features stainless steel appliances and central A/C for year-round ...

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

Lake Hammock Village

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3 Beds | 2 Baths | 1456 Sq. Ft.

197 Glen Este Blvd.
Haines City, FL 33844

LIKE NEW 2016 MODEL 3/2 SPLIT PLAN

Do Not Miss this Like New, Move-In Ready, 2016 3BR/2BATH Split Plan Jacobsen Home. This Great Home Features: New Paint, New Carpet, 8 Foot Ceilings Throughout, Kitchen has Pantry and Large Breakfast Bar. A Large Storage Shed and Carport are also here. ...

Community Lifestyles: 55+ Communities, Active Retirement

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

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

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1352 Sq. Ft.

1701 W Commerce Ave Lot #202
Haines City, FL 33844

Move-in ready Florida home - Many updates

Discover this welcoming two-bedroom, two-bath home in Heartland Estates, an active 55+ lifestyle community in Haines City, Florida. Whether you're looking for a seasonal getaway or a comfortable year-round residence, this inviting home offers a wonderful ...

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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