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Kissimmee, FL 55+ Retirement Communities and Homes

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Kissimmee, Florida, is a vibrant city offering an exciting lifestyle for active adults 55+. Located near Orlando's world-renowned attractions, Kissimmee provides easy access to theme parks like Walt Disney World and Universal Studios. The city boasts beautiful lakes, such as Lake Tohopekaliga, perfect for boating and fishing. Residents can enjoy a variety of outdoor activities, including golfing at championship courses and exploring the scenic trails in nearby parks. Kissimmee also features a lively downtown area with local shops, restaurants, and cultural events. With its warm climate and diverse entertainment options, Kissimmee is perfect for a dynamic and fulfilling retirement lifestyle.

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.

67 homes | « Prev Next »
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The Landings at Lake Henry - Sun Communities

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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

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The Landings at Lake Henry - Sun Communities

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2 Beds | 2 Baths | 840 Sq. Ft.

405 PLANTATION LANDINGS DR.
Haines City, FL 33844

Site # 0405 Addr: 405 PLANTATION LANDINGS DR.

Sellers take pride in the home and it shows! Fully furnished with an open floor plan and laminate flooring throughout. This home boast natural lighting, a large primary bedroom has ample room for a king size bed and several other pieces of furniture, ...

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

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Royal Palm Village - Sun Communities

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2 Beds | 1 Baths | 728 Sq. Ft.

3000 US HWY 17/92 W, LOT #66
Haines City, FL 33844

Site # 0066 Addr: 3000 US HWY 17/92 W, LOT #66

This stunning home is truly a hidden gem and an absolute must-see! Nestled on a corner lot, it offers a serene escape with its beautiful screened-in porch, perfect for enjoying cool shade on those scorching days. Step inside to discover a fully remodeled ...

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

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  • 59 BUTLER BLVD.
  • 59 BUTLER BLVD.
  • 59 BUTLER BLVD.
  • 59 BUTLER BLVD.
  • 59 BUTLER BLVD.
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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. 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

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  • 199 Glen Este Blvd.
  • 199 Glen Este Blvd.
  • 199 Glen Este Blvd.
  • 199 Glen Este Blvd.
  • 199 Glen Este Blvd.
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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 SPLIT-PLAN PRICED TO SELL

Owner is Motivated to sell this Brand New Open Bright and Airy 3BR / 2Bath Split-Plan Home 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. ...

Community Lifestyles: 55+ Communities, Active Retirement

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  • 1701 W Commerce Ave Lot 54
  • 1701 W Commerce Ave Lot 54
  • 1701 W Commerce Ave Lot 54
  • 1701 W Commerce Ave Lot 54
  • 1701 W Commerce Ave Lot 54
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Heartland Estates

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2 Beds | 2 Baths | 1082 Sq. Ft.

1701 W Commerce Ave Lot 54
Haines City, FL 33844

Price includes Golf Cart!!!

We are thrilled to present a stunning home that boasts numerous upgrades and unique features. Imagine a home where the roof, plumbing, and hot water heater were all recently upgraded in 2024, offering you peace of mind and modern convenience. The new ...

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

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  • 1701 W Commerce Ave Lot 116
  • 1701 W Commerce Ave Lot 116
  • 1701 W Commerce Ave Lot 116
  • 1701 W Commerce Ave Lot 116
  • 1701 W Commerce Ave Lot 116
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Heartland Estates

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2 Beds | 2 Baths

1701 W Commerce Ave Lot 116
Haines City, FL 33844

Rent includes lawn care, rubbish and tax pass-on charge

.Dear Potential Homebuyer, 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 ...

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

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  • 1701 W Commerce Ave Lot 192
  • 1701 W Commerce Ave Lot 192
  • 1701 W Commerce Ave Lot 192
  • 1701 W Commerce Ave Lot 192
  • 1701 W Commerce Ave Lot 192
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Heartland Estates

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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

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  • 74 Silver Crest Dr.
  • 74 Silver Crest Dr.
  • 74 Silver Crest Dr.
  • 74 Silver Crest Dr.
  • 74 Silver Crest Dr.
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Lake Hammock Village

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2 Beds | 2 Baths | 1252 Sq. Ft.

74 Silver Crest Dr.
Haines City, FL 33844

BRAND NEW 2/2 +DEN SPLIT-PLAN HOME

Owner is Motivated to sell this Brand New 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 ...

Community Lifestyles: 55+ Communities, Active Retirement

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  • 120 Silver Crest Dr.
  • 120 Silver Crest Dr.
  • 120 Silver Crest Dr.
  • 120 Silver Crest Dr.
  • 120 Silver Crest Dr.
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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

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 and Counter space, along with ...

Community Lifestyles: 55+ Communities, Active Retirement

Show Details Get Home Packet
  • 1701 W. Commerce Ave. Lot 107
  • 1701 W. Commerce Ave. Lot 107
  • 1701 W. Commerce Ave. Lot 107
  • 1701 W. Commerce Ave. Lot 107
  • 1701 W. Commerce Ave. Lot 107
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Heartland Estates

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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

Show Details Get Home Packet
  • 3000 US HWY 17/92 W LOT #633
  • 3000 US HWY 17/92 W LOT #633
  • 3000 US HWY 17/92 W LOT #633
  • 3000 US HWY 17/92 W LOT #633
  • 3000 US HWY 17/92 W LOT #633
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Royal Palm Village - Sun Communities

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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 . Move in Ready! This cozy abode features a convenient 1 car garage, perfect for storing all of your outdoor essentials. The spacious screened back porch ...

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

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  • 107 Reineke Rd.
  • 107 Reineke Rd.
  • 107 Reineke Rd.
  • 107 Reineke Rd.
  • 107 Reineke Rd.
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Lake Hammock Village

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3 Beds | 2 Baths | 1140 Sq. Ft.

107 Reineke Rd.
Haines City, FL 33844

Open, Spacious, Move-In Ready 3/2 Split Plan Home

Open, Spacious 3BR / 2Bath Split-Plan Home is Move-in Ready. This Home Features: Custom Kitchen with loads of cabinet and counter space, Quartz Countertops, Wrap around Counter Bar, S/S Appliances. Washer and Dryer included, also has a Deep Utility Sink ...

Community Lifestyles: 55+ Communities, Active Retirement

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  • 342 ASHLEY DRIVE
  • 342 ASHLEY DRIVE
  • 342 ASHLEY DRIVE
  • 342 ASHLEY DRIVE
  • 342 ASHLEY DRIVE
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The Landings at Lake Henry - Sun Communities

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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

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  • 3000 US HWY 17/92 W, LOT #123
  • 3000 US HWY 17/92 W, LOT #123
  • 3000 US HWY 17/92 W, LOT #123
  • 3000 US HWY 17/92 W, LOT #123
  • 3000 US HWY 17/92 W, LOT #123
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Royal Palm Village - Sun Communities

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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)

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Lake Hammock Village

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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

Show Details Get Home Packet
  • 3000 US HWY 17/92 W, LOT #520
  • 3000 US HWY 17/92 W, LOT #520
  • 3000 US HWY 17/92 W, LOT #520
  • 3000 US HWY 17/92 W, LOT #520
  • 3000 US HWY 17/92 W, LOT #520
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Royal Palm Village - Sun Communities

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3 Beds | 2 Baths | 1344 Sq. Ft.

3000 US HWY 17/92 W, LOT #520
Haines City, FL 33844

Site # 0520 Addr: 3000 US HWY 17/92 W, LOT #520

Welcome to this charming 3 bedroom, 2 bathroom manufactured home. Boasting spacious walk-in closets, a cozy dining area, and a relaxing screened porch, this property is perfect for those seeking comfort and convenience. Step inside and be greeted by ...

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

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  • 94 TARA LANE
  • 94 TARA LANE
  • 94 TARA LANE
  • 94 TARA LANE
  • 94 TARA LANE
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The Landings at Lake Henry - Sun Communities

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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. New carpet in bedrooms installed April 2025. The efficient kitchen features ...

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

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Royal Palm Village - Sun Communities

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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)

Show Details
  • 1701 W Commerce Ave Lot 204
  • 1701 W Commerce Ave Lot 204
  • 1701 W Commerce Ave Lot 204
  • 1701 W Commerce Ave Lot 204
  • 1701 W Commerce Ave Lot 204
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Heartland Estates

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3 Beds | 2 Baths | 1430 Sq. Ft.

1701 W Commerce Ave Lot 204
Haines City, FL 33844

RARE 3B/2B PERIMETER LOT as-is needs roof and plumbing Approx $18K

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

Show Details Get Home Packet

Kissimmee, Florida, is a vibrant city offering an exciting lifestyle for active adults 55+. Located near Orlando's world-renowned attractions, Kissimmee provides easy access to theme parks like Walt Disney World and Universal Studios. The city boasts beautiful lakes, such as Lake Tohopekaliga, perfect for boating and fishing. Residents can enjoy a variety of outdoor activities, including golfing at championship courses and exploring the scenic trails in nearby parks. Kissimmee also features a lively downtown area with local shops, restaurants, and cultural events. With its warm climate and diverse entertainment options, Kissimmee is perfect for a dynamic and fulfilling retirement lifestyle.

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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