Community Search:

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.

147 homes | « Prev Next »
Bedrooms

Bathrooms
Square Feet
-

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 864 Sq. Ft.

336 ASHLEY DRIVE
Haines City, FL 33844

Site # 0336 Addr: 336 ASHLEY DRIVE

This charming 2-bedroom, 2 bath home is located in the desirable 55+ community. The home features an extended driveway, a brand new carport, and two screened in porches perfect for enjoying Florida s sunshine. Inside, you ll find a bright, open layout ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

-

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1040 Sq. Ft.

342 ASHLEY DRIVE
Haines City, FL 33844

Site # 0342 Addr: 342 ASHLEY DRIVE

This beautiful home comes partially furnished! This spacious home features an open floor plan with natural lighting throughout. The kitchen-living room ,eat in kitchen nook combo is great for entertaining. Eat in kitchen features bay windows and a ...

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

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 1 Baths | 1296 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)

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 1.5 Baths | 770 Sq. Ft.

134 MAGNOLIA LANE
Haines City, FL 33844

Site # 0134 Addr: 134 MAGNOLIA LANE

Welcome to this beautifully updated 2 bedroom, 1.5 bathroom home located in a highly sought after 55+ community. This charming residence offers modern updates and timeless comfort, featuring gleaming hardwood flooring throughout for a warm and inviting ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

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

Heartland Estates

Nearby Location MatchNearby Location Match

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

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

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 | 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

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

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.

Easy Compare

Compare Clear List 
X

Browse cities within Central Florida and Orlando

America's Top 100 Best Master-Planned Communities

Featured Communities

Walden Woods - Sun Communities

Walden Woods - Sun Communities

7193 West Walden Woods Drive Homosassa FL 34446

Walden Woods is a gated, 55+ retirement community that offers beautiful manufactured homes paired with a relaxed and enjoyable lifestyle. ...

 

17 homes $59,900 - $129,900

7193 West Walden Woods Drive Homosassa, FL 34446

Visit Showcase
 
 

Holiday Park

Holiday Park

4141 New Tampa Hwy Lakeland FL 33815

Holiday Park is an engaging, resort-style 55+ manufactured home community in Lakeland, FL, nestled between Orlando and Tampa on 4141 ...

 

4 homes $3,600 - $5,900

4141 New Tampa Hwy Lakeland, FL 33815

Visit Showcase
 
 

Sweetwater Oaks

Sweetwater Oaks

3151 NW 44th Ave Lot 1 Ocala FL 34482

Imagine the pleasure of living among cordial neighbors and pleasant surroundings within the charming community of Sweetwater Oaks. Our 45 ...

 

27 homes $58,000 - $99,999

3151 NW 44th Ave Lot 1 Ocala, FL 34482

Visit Showcase
 
 

Colony In The Wood - Sun Communities

Colony In The Wood - Sun Communities

4000 South Clyde Morris Blvd. Port Orange FL 32129

Colony in the Wood, Port Orange, FL is a community with activities and a lifestyle specifically designed for adults ...

 

2 homes $73,000 - $74,995

4000 South Clyde Morris Blvd. Port Orange, FL 32129

Visit Showcase
 
Four Lakes

My Saved Searches

Sign In or Create your free account to see your saved searches.

 

Welcome, Guest!   Sign InSign Up

panhandle florida northern florida upper atlantic coast and jacksonville central florida and orlando space coast tampa bay lower gulf coast florida lower atlantic coast and miami