Kissimmee Homes with Sidewalks Community Features

3 Beds ⋅ 2 Baths ⋅ Osprey Ridge SubDv. ⋅ 34744 Zip Code

### EXPERIENCE THE LIFESTYLE. EMBRACE THE CULTURE. LOVE WHERE YOU LIVE! **A home is more than four walls—it’s where memories are created, traditions begin, and life’s best moments unfold.** Welcome to an exceptional opportunity to experience the energy, convenience, and lifestyle of Central Florida’s sought-after Lake Nona area. Built in 2019, this inviting 3-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of modern comfort, thoughtful design, and everyday functionality. From the moment you step inside, you'll appreciate the bright, open-concept floor plan designed to bring people together. Whether you're hosting friends for dinner, celebrating family milestones, or enjoying a quiet evening at home, the spacious great room provides a welcoming atmosphere filled with natural light. At the heart of the home, the beautifully appointed kitchen features crisp white cabinetry, sleek countertops, stainless steel appliances, and a convenient breakfast bar. It's the perfect gathering place for morning coffee, meaningful conversations, and meals shared with those who matter most. The spacious primary suite offers a peaceful escape from the demands of everyday life, complete with a private ensuite bathroom. Two additional bedrooms provide versatile spaces to accommodate your lifestyle, whether you envision a comfortable guest retreat, creative workspace, or room to grow. **FLORIDA LIVING STARTS RIGHT OUTSIDE YOUR DOOR!** Step onto your covered patio and imagine relaxing with your morning coffee, entertaining friends on a beautiful Florida afternoon, or unwinding beneath the evening sky. The vinyl-fenced backyard offers privacy and space to enjoy the outdoor lifestyle that makes Central Florida living so special. **DISCOVER THE ENERGY AND CULTURE OF LAKE NONA!** Living near Lake Nona means being connected to one of Central Florida's most exciting and evolving communities. Discover a lifestyle shaped by innovation, wellness, recreation, and a vibrant local culture. From unique dining experiences and community gatherings to nearby parks, shopping, and entertainment, there's always something new to explore. With convenient access to Medical City, SR 417, and Orlando International Airport, you're connected to major employment centers, travel destinations, and everything the greater Orlando area has to offer. **THIS IS MORE THAN A PLACE TO LIVE. IT'S A PLACE TO BUILD YOUR FUTURE.** Whether you're buying your first home, beginning a new chapter, or simply looking for a place where comfort meets opportunity, this home invites you to experience the very best of the Central Florida lifestyle. **Your next chapter is waiting. Make it extraordinary. Schedule your private showing today!**

4561 Gadwall Drive, 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

$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

$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

$384,990

3 Beds ⋅ 2 Baths ⋅ Westwood Forest SubDv. ⋅ 34744 Zip Code

This well-maintained 3-bedroom, 2-bath home combines major updates, inviting indoor and outdoor spaces, and NO HOA. Vaulted ceilings and an open living and dining layout create an airy, welcoming feel, with tile flooring throughout the main living areas. The kitchen features updated countertops, contrasting cabinetry, a decorative tile backsplash, and a breakfast bar overlooking the living space—ideal for staying connected while preparing meals. Glass doors open to the backyard for easy indoor-outdoor entertaining. The home has been thoughtfully updated with renovated bathrooms, newer windows, fresh interior paint, a recently replaced A/C system, and a whole-house repipe. The roof was replaced in 2015. Outside, a wide paver driveway and coordinating front walkway create an inviting arrival. The fully fenced backyard offers a patio for outdoor seating and a generous lawn with room to relax, entertain, play, or garden. An attached two-car garage adds everyday convenience. Conveniently located near Florida’s Turnpike and shopping, dining, and entertainment at The Loop, this Kissimmee home puts Central Florida conveniences within easy reach. With major improvements already completed, comfortable gathering spaces, and no HOA, 2944 Oak Run Blvd is one you will want to see.

2944 Oak Run Boulevard, Kissimmee

$480,000

5 Beds ⋅ 3 Baths ⋅ Springlake Village Ph 5b SubDv. ⋅ 34744 Zip Code

Affordability and luxury meets the Lake Nona lifestyle in Spring Lake Village, a gated community with resort-style amenities and convenient access to restaurants, shopping, healthcare, entertainment, parks, and trails. This home offers five spacious bedrooms, three full bathrooms, and approximately 2,800 square feet of living space. The first-floor primary suite provides a comfortable private retreat. A modern kitchen opens to the family room, creating a welcoming space for everyday living and entertaining. Community amenities include heated pools, a fitness center, tennis and basketball courts, a sand volleyball court, shuffleboard courts, and a full-size soccer field. The clubhouse features a community lounge and game room. Outdoor amenities include playgrounds, a dog park, walking trails, and scenic ponds. Enjoy convenient access to Lake Nona’s medical and educational centers, local events, and Orlando International Airport. Schedule a private showing to explore this home and all that Spring Lake Village has to offer.

3833 Siskin Drive, 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

$269,900

4 Beds ⋅ 4 Baths ⋅ Heritage Key Villas Ph 1 & 2 SubDv. ⋅ 34744 Zip Code

Virtually Staged. Start your morning with coffee on the screened lanai overlooking the pond. Sliding glass doors connect the lanai to the living and dining areas, so you can enjoy the water view indoors or out. The kitchen opens to the living area and features a granite-topped island with seating for four, stainless steel appliances, and ample cabinet storage. Tile flooring runs throughout the main living spaces. Spend an afternoon at the community pool or head to the playground. The Kissimmee location offers convenient access to Florida Turnpike, LYNX bus service along U.S. 192, local dining and shopping, medical facilities, and area entertainment and attractions. Schedule your private showing and come see the pond view for yourself.

2007 Piedmont Lane, 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

$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

$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

$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

Kissimmee Homes with Sidewalks Community Features

Newest Kissimmee Homes with Sidewalks Community Features

How much is your home worth?

How much is your home worth?