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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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Bedrooms

Bathrooms
Square Feet
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Four Lakes Golf Club

Exact Location MatchExact Location Match

3 Beds | 2 Baths | 2172 Sq. Ft.

2121 Lawsonia Loop (LOT #434)
Winter Haven, FL 33881

434

LAKEFRONT LIVING WITH PRIVATE DOCK! 1996 Jacobsen Lot 434 |Reduced again to $129,900 | 3 Bed | 2 Bath | 2,172 sq. ft. MOTIVATED SELLER ~ NEW REDUCED PRICE! Nestled on the Chain of Lakes, you'll find a spacious three bed, two bath home with a 35 x 10 ...

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

Four Lakes Golf Club

Exact Location MatchExact Location Match

2 Beds | 2 Baths | 1474 Sq. Ft.

928 La Quinta Blvd. (LOT #210)
Winter Haven, FL 33881

210

CHARMING GOLF COURSE GETAWAY! 1998 Lot 210 | $115,000 | Two Bed | Two Bath | 1,474 sq. ft. NEW REDUCED PRICE FROM $129,900 to $115,000! Located on the main drive of La Quinta Blvd. is a darling two bed, two bath gem perfectly situated on the 9th tee ...

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

Four Lakes Golf Club

Exact Location MatchExact Location Match

2 Beds | 2 Baths | 1148 Sq. Ft.

1420 Wild Dunes Ct. (LOT #58)
Winter Haven, FL 33881

'58

FABULOUS HOME ON PERIMETER LOT! 1999 Homes of Merit Lot 58 | Reduced to $84,900 | Two Bed | Two Bath | 1,148 sq. ft. NEW REDUCED PRICE ~ SAVE! Located adjacent to a Florida preserve, you will find a quiet place to spend the winter or stay all year! ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

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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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

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)

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

Just Listed!!! 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 ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

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2 Beds | 2 Baths | 952 Sq. Ft.

209 DIXIE CIRCLE
Haines City, FL 33844

Site # 0209 Addr: 209 DIXIE CIRCLE

Step into this beautifully designed home, featuring a spacious open floor plan that perfectly blends comfort and style. Enjoy the sleek look of laminate flooring throughout the main living areas, while plush carpet adds warmth to the cozy bedrooms. The ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

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)

Heartland Estates

Nearby Location MatchNearby Location Match

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

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

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 960 Sq. Ft.

141 Winterdale Dr. S
Lake Alfred, FL 33850

Site # 0209 Addr: 141 Winterdale Dr. S

This charming 2-bedroom, 2-bath partially furnished home within a beautiful 55+ gated community boasts a bright open floor plan, featuring lovely bay windows in the dining area which lead into a kitchen just steps away. Enjoy the spacious living room ...

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

Lake Hammock Village

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

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

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1198 Sq. Ft.

173 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0173 Addr: 173 CYPRESS WAY

Beautifully updated 2-bedroom, 2-bath waterfront home in a desirable 55+ golf course community! Fully furnished and move-in ready, home features an open-concept floor plan connecting the kitchen, dining, and living areas, creating a bright, open, and ...

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

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1800 Sq. Ft.

149 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0149 Addr: 149 CYPRESS WAY

Welcome to this spacious 2 bed, 2 bath + den home with 1-car attached garage located in Cypress Greens active 55+ golf and tennis community. This home features an open layout with newer laminate in living areas, tile in kitchen and baths, and carpeted ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

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

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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Four Lakes

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