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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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Cypress Greens - Sun Communities

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2 Beds | 2 Baths | 1568 Sq. Ft.

21 CYPRESS LOOP
Lake Alfred, FL 33850

Site # 0021 Addr: 21 CYPRESS LOOP

Discover this beautifully maintained 2-bed, 2-bath home offering 1,868 total sq. ft. of comfortable living space Cypress Greens golf and tennis community! The split floor plan includes a large living room, tile kitchen with stainless steel appliances, ...

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

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 840 Sq. Ft.

249 DIXIE CIRCLE
Haines City, FL 33844

Site # 0249 Addr: 249 DIXIE CIRCLE

Located in a 55+ community this beautiful modern home featuring laminate flooring throughout and thoughtfully designed upgrades that make everyday living both stylish and comfortable. This bright, open floor plan offers an inviting kitchen with stainless ...

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

Kings Pointe - Sun Communities

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2 Beds | 2 Baths | 1104 Sq. Ft.

216 Trade Wind Ct.
Lake Alfred, FL 33850

Site # 0133 Addr: 216 Trade Wind Ct.

This move-in ready 2-bedroom, 2-bath home offers the perfect blend of comfort and functionality. Featuring a unique bonus addition and an open floor plan, the layout provides plenty of space for both relaxing and entertaining. Every area of the home ...

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

Blue Heron Bay

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2 Beds | 2 Baths

145 Blue Heron Blvd
Haines City, FL 33844

This spacious 2.0 bed 2.0 bath manufactured home at Blue Heron Bay in Haines City, FL offers a comfortable and cozy living space with 1326 square feet of living area. Built in 1997 by Palm Harbor, this well-maintained home features a large living room, ...

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

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)

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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3 Beds | 2 Baths | 1344 Sq. Ft.

3000 US HWY 17/92 W LOT #625
Haines City, FL 33844

Site # 0625 Addr: 3000 US HWY 17/92 W LOT #625

Step into this beautifully designed home featuring a bright, open-concept layout perfect for comfortable everyday living and entertaining. The modern kitchen shines with stainless steel appliances, added storage space, and a functional layout that flows ...

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

Kings Pointe - Sun Communities

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2 Beds | 2 Baths | 1200 Sq. Ft.

142 Winterdale Dr. N
Lake Alfred, FL 33850

Site # 0185 Addr: 142 Winterdale Dr. N

WOW! Don t miss the opportunity to own this beautiful 2-bedroom, 2-bath home featuring a spacious garage and ample storage. The open-concept living room, dining area, and kitchen create an inviting space that s perfect for entertaining. The large primary ...

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

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)

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)

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

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

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

Cypress Greens - Sun Communities

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2 Beds | 2 Baths | 1800 Sq. Ft.

149 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0149 Addr: 149 CYPRESS WAY

Welcome to this spacious unfurnished 2 bed, 2 bath + den home with a 1-car attached garage, offering approximately 1,400 square feet of living space, located in the Cypress Greens active 55+ golf and tennis community. This newer home features an open ...

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

Lake Hammock Village

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2 Beds | 2 Baths | 1120 Sq. Ft.

120 Silver Crest Dr.
Haines City, FL 33844

MOVE IN READY 2/2 SPLIT-PLAN HOME

OWNER IS MOTIVATED TO SELL This Open, Spacious 2BR / 2Bath Split-Plan Home is Move-in Ready. Home has Brand New Roof, Complete Interior Paint, Including all Cabinets, New Faucets and Light Fixtures. This Home also Features: Kitchen with loads of Cabinet ...

Community Lifestyles: 55+ Communities, Active Retirement

Cypress Greens - Sun Communities

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2 Beds | 2 Baths | 1352 Sq. Ft.

49 CREEK CIRCLE
Lake Alfred, FL 33850

Site # 0049 Addr: 49 CREEK CIRCLE

Discover comfort and convenience in this partially furnished 2 bedroom, 2 bath home located in a vibrant 55+ golf community. Wake up to beautiful golf course views and enjoy the ease of having a golf cart included. The spacious primary suite features ...

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

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

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1248 Sq. Ft.

94 PALM LANE
Lake Alfred, FL 33850

Site # 0094 Addr: 94 PALM LANE

Charming 2-bedroom, 2-bath home comes partially furnished and includes a golf cart! Enjoy peace of mind with 2023 updates new roof, HVAC system, and stainless-steel kitchen appliances. The spacious primary suite features an ensuite bath with walk-in ...

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

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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