Kissimmee Homes with Sidewalks Community Features

Kissimmee Homes with Sidewalks Community Features

Welcome to Kissimmee, Florida – a vibrant community nestled in the heart of Osceola County, just a stone's throw away from the magic of Orlando! Known for its rich cultural heritage and stunning natural beauty, Kissimmee offers an enchanting blend of suburban charm and urban convenience. With its proximity to world-renowned theme parks, pristine lakes, and lush parks, residents can enjoy endless recreational opportunities right at their doorstep.

One of the standout features of Kissimmee is its commitment to creating a walkable community. Many neighborhoods boast homes with sidewalks, fostering a sense of connection among residents. Imagine taking leisurely strolls along tree-lined streets, with friendly neighbors waving hello and children riding their bikes in a safe, inviting environment. Sidewalks not only enhance the aesthetic appeal of the community but also promote a healthy lifestyle, encouraging families to explore local parks, shops, and dining options.

Kissimmee’s real estate market offers a variety of homes, from charming single-family residences to modern townhouses, all designed with community living in mind. This region is perfect for families, retirees, and everyone in between, providing a welcoming atmosphere where you can truly feel at home.

With its unique blend of convenience, community, and charm, Kissimmee is not just a place to live – it’s a place to thrive. Explore our listings today and discover your dream home in this delightful Florida gem, where every day feels like a vacation!

Newest Kissimmee Homes with Sidewalks Community Features

4423 Biscayne Breeze Way, Kissimmee
$559,900
4 Beds ⋅ 3 Baths ⋅ North Point SubDv. ⋅ 34744 Zip Code
A screened saltwater pool and spa, a wooded backdrop, and a first-floor primary suite set the stage for this inviting North Point home, where comfortable interior spaces meet an exceptional outdoor living area. Situated on a fenced homesite within a gated community, this two-story Home Dynamics residence offers 2,601 square feet, four bedrooms, two full baths, and a half bath. The primary suite is conveniently located on the first floor, while three additional bedrooms and a versatile loft occupy the second level. A paver driveway and covered front porch lead to a decorative glass entry door and a bright, open interior. Diagonally laid tile connects the main living spaces, while arched openings and tray ceiling details add character. The generous front living room provides room to arrange both conversation and media areas, with windows bringing in natural light along the side of the home. Beyond it, the kitchen and dining spaces open toward the pool, keeping the rear of the home connected to the lanai. White cabinetry with crown trim, granite countertops, a tile backsplash, and stainless steel appliances give the kitchen a crisp, cohesive finish. An island with breakfast-bar seating creates a natural gathering point, complemented by pendant lighting and a separate breakfast nook. The adjoining dining room has a tray ceiling and French doors to the covered outdoor sitting area, making it easy to carry meals and conversation outside. A first-floor laundry room, included washer and dryer, nearby half bath, and attached two-car garage support everyday convenience. Positioned at the rear of the first floor, the primary suite has carpet underfoot, a tray ceiling, a ceiling fan, and French doors opening directly to the lanai. A walk-in closet with shelving and hanging storage leads into a spacious private bath with dual sinks, granite counters, a soaking tub, a separate glass-enclosed shower, and a private water closet. Upstairs, three carpeted bedrooms share a full bath with dual sinks and a tub-shower combination. One bedroom offers an especially generous, extended layout, while the open loft provides additional space for a desk, hobbies, or a second lounge. The outdoor living area is the home's defining feature. A broad screened enclosure surrounds the heated saltwater pool and attached spa, with a raised, stone-accented spillover adding texture to the poolscape. The covered lanai offers shade for seating beneath a ceiling fan, while the surrounding deck leaves room for dining and lounging beside the water. Beyond the enclosure, the fenced lawn and trees along the rear create a green backdrop, with neighboring homes to either side. French-door access from both the dining area and primary bedroom makes the pool and lanai a natural extension of the interior. Updates include a Puronics reverse-osmosis water filtration system installed in April 2025 and an IntelliChlor salt cell replaced in September 2026. A water softener is also included. North Point offers gated entry, a community pool, and a playground. With a Kissimmee address near the Lake Nona area, this home pairs community amenities with the everyday appeal of a main-floor suite and a poolside setting of its own.

4423 Biscayne Breeze Way, Kissimmee

1900 Southbury Drive, Kissimmee
$514,335
5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Hayden. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept layout. The kitchen overlooks the dining area and great room, while having a view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, beautiful quartz countertops and stainless-steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play, a bedroom, and full bathroom. As we head up to the second floor, we are greeted with bedroom one that features an en suite bathroom as well as three additional bedrooms that surround a second living area, a full bathroom, and a laundry area. Like all homes in Kindred, the Hayden includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1900 Southbury Drive, Kissimmee

1952 Southbury Drive, Kissimmee
$380,990
3 Beds ⋅ 2 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Virtually Staged. Under Construction. Kindred present the Astor. This all-concrete block constructed single family home features 3 bedrooms and 2 bathrooms. As you enter the foyer you are greeted by with an open concept living space. The kitchen overlooks the dining and living room, while having a view to the oversized outdoor living space. The well-appointed kitchen features an island with bar seating, plentiful cabinet with beautiful quartz countertops and stainless steel appliances, making entertaining a breeze. Bedroom one, located off the living space, has an en suite bathroom with double vanity and spacious walk-in closet providing ample space for storage. Two additional bedrooms and one full bath are located at the front of the home along with a coat closet, linen closet, and laundry room. Like all homes in Kindred, the Astor includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries. *

1952 Southbury Drive, Kissimmee

2220 Rolling Hills Road N, Kissimmee
$361,990
3 Beds ⋅ 3 Baths ⋅ Kindred Townhome SubDv. ⋅ 34744 Zip Code
Virtually Staged. Under Construction. Kindred presents the Stratford. This spacious all concrete block construction end unit townhome optimizes living space with an elevated design featuring 3 bedrooms, 2.5 baths and a 2 Car Garage. As you enter the foyer, you’ll step into a home that reflects your style with an open concept dining area, living room and a spacious kitchen with bar seating. The kitchen is complete with a pantry, stainless steel appliances, and quartz countertops making cooking and cleaning a breeze. Towards the back of the townhome you will find a half bathroom and private entry from the garage. As you head up to the second floor you are greeted with the 3 bedrooms and 2 bathrooms. The bedroom one-bathroom impresses with double bowl vanity, and modern shower/tub space as well as a spacious walk in closet. The second floor is complete with two guest bedrooms, an additional bathroom, and an enclosed laundry room space. This home features modern details that elevate your personal style. Like all homes in Kindred, the Stratford includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2220 Rolling Hills Road N, Kissimmee

2218 Rolling Hills Road N, Kissimmee
$347,990
3 Beds ⋅ 3 Baths ⋅ Kindred Townhome SubDv. ⋅ 34744 Zip Code
Virtually Staged. Under Construction. Kindred presents the Sterling. This spacious all concrete block construction townhome optimizes living space with an elevated design featuring 3 bedrooms, 2.5 baths and a 2 Car Garage. As you enter the foyer, you’ll step into a home that reflects your style with an open concept dining area, living room and a spacious kitchen with bar seating. The kitchen is complete with a pantry, stainless steel appliances, and upgraded countertops making cooking and cleaning a breeze. Towards the back of the townhome you will find a half bathroom and private entry from the garage. As you head up to the second floor you are greeted with the 3 bedrooms and 2 bathrooms. The bedroom one-bathroom impresses with double bowl vanity, and modern shower/tub space as well as a spacious walk in closet. The second floor is complete with two guest bedrooms, an additional bathroom, and an enclosed laundry room space. This home features modern details that elevate your personal style. Like all homes in Kindred, the Sterling includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2218 Rolling Hills Road N, Kissimmee

2216 Rolling Hilld Road N, Kissimmee
$347,990
3 Beds ⋅ 3 Baths ⋅ Kindred Townhome SubDv. ⋅ 34744 Zip Code
Virtually Staged. Under Construction. Kindred presents the Sterling. This spacious all concrete block construction townhome optimizes living space with an elevated design featuring 3 bedrooms, 2.5 baths and a 2 Car Garage. As you enter the foyer, you’ll step into a home that reflects your style with an open concept dining area, living room and a spacious kitchen with bar seating. The kitchen is complete with a pantry, stainless steel appliances, and upgraded countertops making cooking and cleaning a breeze. Towards the back of the townhome you will find a half bathroom and private entry from the garage. As you head up to the second floor you are greeted with the 3 bedrooms and 2 bathrooms. The bedroom one-bathroom impresses with double bowl vanity, and modern shower/tub space as well as a spacious walk in closet. The second floor is complete with two guest bedrooms, an additional bathroom, and an enclosed laundry room space. This home features modern details that elevate your personal style. Like all homes in Kindred, the Sterling includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2216 Rolling Hilld Road N, Kissimmee

2214 Rolling Hills Road N, Kissimmee
$365,990
3 Beds ⋅ 3 Baths ⋅ Kindred Townhome SubDv. ⋅ 34744 Zip Code
Virtually Staged. Under Construction. Kindred presents the Stratford. This spacious all concrete block construction end unit townhome optimizes living space with an elevated design featuring 3 bedrooms, 2.5 baths and a 2 Car Garage. As you enter the foyer, you’ll step into a home that reflects your style with an open concept dining area, living room and a spacious kitchen with bar seating. The kitchen is complete with a pantry, stainless steel appliances, and quartz countertops making cooking and cleaning a breeze. Towards the back of the townhome you will find a half bathroom and private entry from the garage. As you head up to the second floor you are greeted with the 3 bedrooms and 2 bathrooms. The bedroom one-bathroom impresses with double bowl vanity, and modern shower/tub space as well as a spacious walk in closet. The second floor is complete with two guest bedrooms, an additional bathroom, and an enclosed laundry room space. This home features modern details that elevate your personal style. Like all homes in Kindred, the Stratford includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2214 Rolling Hills Road N, Kissimmee

2454 Quail Run Boulevard N, Kissimmee
$355,000
3 Beds ⋅ 2 Baths ⋅ Quail Hollow Ph 3 SubDv. ⋅ 34744 Zip Code
Welcome home to this inviting Kissimmee property, offering the perfect blend of comfort, functionality, and Florida lifestyle! NO HOA! The well-appointed kitchen features beautiful wood cabinetry, granite countertops, and stainless-steel appliances, creating a stylish and practical space for everyday living and entertaining. Enjoy the best of indoor-outdoor living in the screened-in Florida room, an ideal spot to relax, enjoy your morning coffee, or unwind while taking in the beautiful Florida weather. The fenced-in backyard offers added privacy, along with plenty of room for outdoor activities, entertaining, pets, or creating your very own garden oasis. Conveniently located near schools, parks, lakes, shopping, dining, entertainment and medical facilities, this home puts everyday conveniences and recreational opportunities right at your fingertips. Just minutes from the charm and attractions of Historic Downtown Kissimmee and its beautiful lakefront, you'll enjoy easy access to local shops, restaurants, community events, and waterfront activities. The property is also approximately 5 minutes from the emerging Neo City development, a growing technology and innovation hub bringing exciting economic development and investment potential to the area. Located right off of major highways, such as 192 and Florida Turnpike, making it convenient for commuting. Whether you're looking for a place to call home, a property with an open floor plan to enjoy the Florida lifestyle, or an opportunity to invest in a growing area, this Kissimmee property is one you won't want to miss!

2454 Quail Run Boulevard N, Kissimmee

1920 Southbury Drive, Kissimmee
$496,490
5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Hayden. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept layout. The kitchen overlooks the dining area and great room, while having a view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, beautiful quartz countertops and stainless-steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play, a bedroom, and full bathroom. As we head up to the second floor, we are greeted with bedroom one that features an en suite bathroom as well as three additional bedrooms that surround a second living area, a full bathroom, and a laundry area. Like all homes in Kindred, the Hayden includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1920 Southbury Drive, Kissimmee

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