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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 | 1196 Sq. Ft.

1701 W Commerce Ave Lot #244
Haines City, FL 33844

New roof 2022 - New flooring 2022

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 well -maintained & loved home has 2 bedrooms & 2 bathrooms, New ...

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

Royal Palm Village - Sun Communities

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2 Beds | 2 Baths | 1352 Sq. Ft.

3000 US HWY 17/92 W, LOT #292
Haines City, FL 33844

Site # 0292 Addr: 3000 US HWY 17/92 W, LOT #292

Welcome to your own slice of waterfront living in Royal Palm Village! This beautifully maintained home offers a rare combination of comfort, natural light, and serene canal views, perfect for relaxing or entertaining. Step inside to find a spacious, ...

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 | 924 Sq. Ft.

211 DIXIE CIRCLE
Haines City, FL 33844

Site # 0211 Addr: 211 DIXIE CIRCLE

Welcome home to this charming and well-maintained residence located in a peaceful 55+ community. This inviting home features a bright and comfortable living area, perfect for relaxing or entertaining, along with a spacious kitchen offering ample cabinet ...

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

Lake Hammock Village

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3 Beds | 2 Baths | 1456 Sq. Ft.

199 Glen Este Blvd.
Haines City, FL 33844

BRAND NEW 3/2 MODEL HOME

Brand New Open Bright and Airy 3BR / 2Bath Split-Plan Home Available NOW! This New Home Features: Open Spacious Living Areas. Kitchen has Large Island with Seating and Lots of Storage, All Upgrade Appliances, and a Walk-In Pantry. Spacious Master Bedroom ...

Community Lifestyles: 55+ Communities, Active Retirement

Heartland Estates

Nearby Location MatchNearby Location Match

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

The Landings at Lake Henry - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1638 Sq. Ft.

352 ASHLEY DRIVE
Haines City, FL 33844

Site # 0352 Addr: 352 ASHLEY DRIVE

Lot 352 PREMIUM Homesite located on the lake Captivating 2023 Clayton Home 2 Bedrooms, 2 Baths plus Den, front porch and rear full size balcony with existing boat dock. The living room provides easy access to the rear balcony with great views to include ...

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

The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 1120 Sq. Ft.

311 MAPLECREST DRIVE
Haines City, FL 33844

Site # 0311 Addr: 311 MAPLECREST DRIVE

This charming 2 bedroom, 2 bathroom home offers comfort and convenience with a modern touch. The updated kitchen features contemporary finishes and ample space for cooking and entertaining, while the spacious living room provides a welcoming area to ...

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

Heartland Estates

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2 Beds | 2 Baths | 1300 Sq. Ft.

1701 W Commerce Ave Lot 159
Haines City, FL 33844

New plumbing & HWT 2023, Granite counter tops, Luxury vinyl floors & more!

Welcome to Heartland Estates an active and fun community! Where your new home awaits you! We have a stunning home to show you, This 2B2B 1300sq ft home comes fully furnished with leather Livingroom set, coffee bar, and beautiful decor throughout. This ...

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

Blue Heron Bay

Nearby Location MatchNearby Location Match

2 Beds | 1.5 Baths

160 Blue Heron Blvd
Haines City, FL 33844

This charming 936 square foot manufactured home, built in 1994 by Fleetwood, offers a comfortable and functional living space in Haines City, FL. Featuring two bedrooms and one and a half bathrooms, the home includes a comfortable living room and dining ...

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1056 Sq. Ft.

3000 US HWY 17/92 W, LOT #540
Haines City, FL 33844

Site # 0540 Addr: 3000 US HWY 17/92 W, LOT #540

Welcome to your home. This delightful 2-bedroom, 2-bathroom house offers comfortable living with all the conveniences you need right at your doorstep. This well-designed, partially furnished home is perfectly situated on the canal with beautiful water ...

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

Heartland Estates

Nearby Location MatchNearby Location Match

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

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. 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

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths

209 Crane Ln.
Haines City, FL 33844

This charming double wide manufactured home, built in 1994 by Fleetwood, offers a comfortable and functional living space with 2 bedrooms and 2 bathrooms. Over 908 sq. ft. INCLUDING the 10' x 14 Enclosed Florida room with A/C and Heat. The interior ...

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

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)

Heartland Estates

Nearby Location MatchNearby Location Match

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

Lake Hammock Village

Nearby Location MatchNearby Location Match

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

Lake Hammock Village

Nearby Location MatchNearby Location Match

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

Royal Palm Village - Sun Communities

Nearby Location MatchNearby Location Match

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)

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

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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