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.

170 homes | « Prev Next »
Bedrooms

Bathrooms
Square Feet
-

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 1 Baths | 576 Sq. Ft.

94 TARA LANE
Haines City, FL 33844

Site # 0094 Addr: 94 TARA LANE

Premium corner lot home, comes partially furnished! Comfortable and cozy home. The living room, kitchen and dining areas are all open which makes it perfect for entertaining. The efficient kitchen features bay windows for natural lighting and breakfast ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 1120 Sq. Ft.

3000 US HWY 17/92 W, LOT #496
Haines City, FL 33844

Site # 0496 Addr: 3000 US HWY 17/92 W, LOT #496

This charming and spacious 2-bedroom, 2-bathroom home is perfectly situated on a desirable corner lot with stunning views in a prime location within the community, just steps from the clubhouse, fitness center, and pools. Featuring an open-concept design ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

3 Beds | 2 Baths | 1540 Sq. Ft.

3000 US HWY 17/92 W, LOT #295
Haines City, FL 33844

Site # 0295 Addr: 3000 US HWY 17/92 W, LOT #295

Welcome to your dream home. This stunning property boasts abundant natural light throughout, making every room feel bright and airy. The open floor plan is perfect for entertaining with a spacious living room, dining area, and large kitchen featuring ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

3 Beds | 2 Baths | 1430 Sq. Ft.

1701 W Commerce Ave Lot 204
Haines City, FL 33844

RARE 3B/2B PERIMETER LOT BACK PATIO WITH SUNBRELLA EXPAN AWNING

Welcome to Heartland Estates, where a warm and inviting community awaits you! We are thrilled to present this exciting, contemporary, partially furnished 3B2B home that perfectly embodies the spirit of relaxed and engaging living. Imagine sipping your ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 1352 Sq. Ft.

3000 US HWY 17/92 W, LOT #247
Haines City, FL 33844

Site # 0247 Addr: 3000 US HWY 17/92 W, LOT #247

Charming Corner-Lot Home with Modern Upgrades This cozy 2-bedroom, 2-bathroom home features beautiful laminate flooring, a versatile guest bedroom with a murphy bed, and a bright living room filled with natural light. Recent upgrades include new electric ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 1196 Sq. Ft.

3000 US HWY 17/92 W, LOT #317
Haines City, FL 33844

Site # 0317 Addr: 3000 US HWY 17/92 W, LOT #317

Welcome to your snowbird paradise! This beautifully upgraded 2-bed, 2-bath home sits on a desirable corner lot and comes fully furnished just bring your toothbrush! Inside, you'll find gorgeous wood flooring, stainless steel appliances, and even a washer ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1252 Sq. Ft.

1701 W Commerce Ave Lot 282
Haines City, FL 33844

New price $119,800, $4,800 Referral fee & Free Rent all of 2025!

LAKESIDE HOME FOR SALE - ALL 6 ROOMS have a view of lake! ~ 2 bedrooms, 2 baths, 1,252 sq. ft., $119,800 *** $4,800 REFERRAL BONUS will be paid to a person or entity who refers Buyer. See NOTE #1 for more details.* *** FREE RENT FOR REMAINDER OF 2025. ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1125 Sq. Ft.

1701 W. Commerce Ave. Lot 250
Haines City, FL 33844

2B/2B year round rental furnished and side by side drive under carport!

Welcome to your new Oasis in the welcoming Community of Heartland Estates! This beautiful & spacious home was deigned for comfort & tranquility. As you arrive you are greeted with its beautiful landscape & side by side covered parking. Once inside you ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

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

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 1044 Sq. Ft.

3000 US HWY 17/92 W, LOT #263
Haines City, FL 33844

Site # 0263 Addr: 3000 US HWY 17/92 W, LOT #263

Welcome to your dream home by the water! Nestled in a serene and picturesque setting, this beautiful 2-bedroom, 2-bathroom fully furnished home is ready for you to move in and start living your best life immediately. Enjoy the sunny Florida weather in ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

3 Beds | 2 Baths | 1358 Sq. Ft.

1701 W. Commerce Ave. 281
Haines City, FL 33844

Contemporary, lakefront home w/huge deck for entertaining

Welcome to Heartland Estates, where a warm and inviting community awaits you! We are thrilled to present this exciting, contemporary, fully furnished 3B2B home that perfectly embodies the spirit of relaxed and engaging living. Imagine sipping your morning ...

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

Lake Hammock Village

Nearby Location MatchNearby Location Match

-

3 Beds | 2 Baths | 1568 Sq. Ft.

180 Glen Este Blvd.
Haines City, FL 33844

SPACIOUS 3/2 SPLIT-PLAN HOME

Move-In Ready, Excellent Condition 3BR / 2Bath Split- Plan Home is Priced to Sell Now. This Home Features: Open Spacious Living Areas, Laminate Flooring Throughout. Kitchen with all Appliances including Washer and Dryer, Morning Room, and a Walk-In Pantry. ...

Community Lifestyles: 55+ Communities, Active Retirement

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

3 Beds | 2 Baths | 1456 Sq. Ft.

3000 US HWY 17/92 W, LOT #497
Haines City, FL 33844

Site # 0497 Addr: 3000 US HWY 17/92 W, LOT #497

Welcome to this beautifully maintained and fully furnished home, located in a peaceful 55+ community! This spacious corner lot home offers the perfect blend of comfort and convenience, featuring a large carport that provides ample parking space. Step ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1144 Sq. Ft.

1701 W Commerce Ave Lot 188
Haines City, FL 33844

Entertainer's dream w/ Lake view from patio, screen room, and sunroom!

Welcome to Heartland Estates, where comfort and convenience meet in a warm and welcoming 55+ community. We are excited to present to you a beautiful home that has undergone extensive renovations in the last three years, making it move-in ready for you ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1040 Sq. Ft.

1701 W Commerce Ave Lot 117
Haines City, FL 33844

Stunning one-of-a-kind Home, completely renovated with premium finishes.

Welcome to Heartland Estates, where comfort and convenience meet in a warm and welcoming 55+ community. We are excited to present to you a beautiful home that has undergone extensive renovations, making it move-in ready and maintenance free for years ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

-

1 Beds | 1 Baths | 528 Sq. Ft.

19 O`HARA DRIVE
Haines City, FL 33844

Site # 0019 Addr: 19 O`HARA DRIVE

This charming 1 bedroom features a functional living room, with an option to close off a section of the living room. This beautiful well-kept home has natural lighting and additional storage space throughout the home. The heart of this home is the modern ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 1456 Sq. Ft.

3000 US HWY 17/92 W LOT #573
Haines City, FL 33844

Site # 0573 Addr: 3000 US HWY 17/92 W LOT #573

Must see home located on an oversized lot with no rear neighbors! Large open concept living in a superior 55+ community. Gorgeous kitchen with plenty of storage space. The kitchen opens into the living room for great entertaining opportunities. Natural ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 1416 Sq. Ft.

3000 US HWY 17/92 W, LOT #541
Haines City, FL 33844

Site # 0541 Addr: 3000 US HWY 17/92 W, LOT #541

A motivated seller has just listed an amazing waterfront property in the desired 55+ community of Royal Palm Village. This Home features a brand new carport and roof aged at 6 months old, central air and duct work as new as January 2025, stove refrigerator ...

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 | 1596 Sq. Ft.

323 ASHLEY DRIVE
Haines City, FL 33844

Site # 0323 Addr: 323 ASHLEY DRIVE

Newly listed home! This 1994 Meri is a perfect getaway from life s hustles and bustles. The home has been updated throughout and features new laminate flooring throughout the home. A large primary bedroom has ample room for a king size bed and several ...

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

-

2 Beds | 2 Baths | 840 Sq. Ft.

108 WILKES DRIVE
Haines City, FL 33844

Site # 0108 Addr: 108 WILKES DRIVE

Charming home comes partially furnished, bright open kitchen with granite countertops and bay windows is great for natural lighting. Laminate flooring throughout, spacious master bedroom with oversized walk in closet and ceilings throughout home. Newer ...

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

Easy Compare

Compare Clear List 
X

Browse cities within Central Florida and Orlando

America's Top 100 Best Master-Planned Communities

Featured Communities

Shadow Wood Village - Sun Communities

Shadow Wood Village - Sun Communities

14709 Shadowwood Blvd. Hudson FL 34667

Welcome to Shadow Wood Village, a 55+ manufactured home community in Hudson, FL, where your dream of Florida homeownership comes ...

 

5 homes $89,995 - $168,995

14709 Shadowwood Blvd. Hudson, FL 34667

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 ...

 

29 homes $74,900 - $116,995

3151 NW 44th Ave Lot 1 Ocala, FL 34482

Visit Showcase
 
 

Shalimar Village MHC

Shalimar Village MHC

6529 Stone Road Port Richey FL 34668

Shalimar Village Manufactured Housing Community located in Port Richey, Florida, is all about lifestyle. ...

 

18 homes $7,500 - $79,995

6529 Stone Road Port Richey, FL 34668

Visit Showcase
 
 

Highland Country Estates

Highland Country Estates

830 North Highway 17/92 DeBary FL 32713

DeBary is hailed as one of Florida’s finest small cities to live in. So, why not enjoy your leisure years ...

 

6 homes $15,000 - $96,900

830 North Highway 17/92 DeBary, FL 32713

Visit Showcase
 
Hawthorne At Leesburg

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