Kissimmee Homes with Trail(s) Amenities

Kissimmee Homes with Trail(s) Amenities

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the excitement of Florida’s attractions with the charm of a close-knit community. Nestled just a stone’s throw from the world-famous Walt Disney World Resort, Kissimmee is a haven for families, retirees, and anyone seeking a sunny getaway. With its picturesque lakes, lush parks, and a plethora of recreational activities, this city offers a lifestyle that is both exhilarating and serene.

Kissimmee boasts a diverse real estate market, with homes that cater to various tastes and budgets. One of the most sought-after features among homebuyers is the presence of trails and outdoor amenities. Imagine stepping out of your front door to find a network of scenic trails winding through beautiful landscapes, perfect for walking, jogging, or cycling. These trails not only promote an active lifestyle but also foster a sense of community as residents often gather to enjoy the great outdoors.

Many neighborhoods in Kissimmee are designed with these amenities in mind, offering residents easy access to parks, playgrounds, and nature reserves. Whether you’re looking for a cozy single-family home or a spacious townhouse, you will find properties that come equipped with access to these trails, enhancing your quality of life.

In Kissimmee, you’re not just buying a home; you’re investing in a lifestyle filled with adventure, community, and the joys of nature. Explore the possibilities today and discover your dream home in this enchanting city!

Newest Kissimmee Homes with Trail(s) Amenities

$441,990
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Cali. This all concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located in the back of the home for privacy, has an en suite bathroom with a double vanity, spacious shower/tub space as well as a spacious walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall you will find a fourth bedroom. This home features a space to fit all your needs. Like all homes in Kindred, the Cali 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.*

1523 Beechmont Drive, Kissimmee
$406,990
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code
Kindred presents the Jemison. A front porch welcomes to you into a one-story all concrete block construction home. Designed to optimize living space with an open concept kitchen that overlooks the versatile great room and covered lanai. The well-appointed kitchen features an island with bar seating, oversized walk in pantry and sleek stainless steel appliances. Bedroom one is located at the rear of the home for privacy and has an en suite bathroom with a double vanity and spacious walk-in closet providing substantial storage space. A second bedroom and bathroom are located at the front of the home. Just off the kitchen, the versatile flex space can be utilized as an office or cozy den. Like all homes in Kindred, the Jemison 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.*

1868 Kindle Street, Kissimmee
$468,990
5 Beds ⋅ 3 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find bedroom two and a full bathroom. As you move upstairs you are greeted with a nice sized living space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet and an en suite bathroom with a double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie 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.*

1908 Howard Mesa Drive, Kissimmee
$474,000
4 Beds ⋅ 3 Baths ⋅ Solivita Ph 5-A SubDv. ⋅ 34759 Zip Code
Virtually Staged. Like-New Calabria Model with Water & Conservation Views and Private In-Law Suite! Welcome to this beautifully maintained 2019 Calabria model featuring 4 bedrooms, 3 bathrooms, a private in-law suite with separate entry, and stunning water and conservation views on a . Ideally located just minutes from the Village Amenities Center, this home offers the perfect combination of comfort, privacy, and convenience. Enter through the screened-in front walkway, where you’ll find the private entrance to the in-law suite as well as the impressive leaded-glass front door. Inside, you’ll discover a spacious open-concept living, dining, and kitchen area designed to take full advantage of the beautiful water and conservation views. The large kitchen features a generous eat-at island/bar, abundant cabinetry with convenient pull-out drawers, beautiful quartz countertops, and a walk-in pantry. The adjoining dining area provides a wonderful view of the screened lanai, water, and conservation area. The spacious primary bedroom offers a tray ceiling, ceiling fan, and a peaceful private view of the water and conservation area. The luxurious primary bath features dual sinks, a large custom walk-in shower, and an enormous walk-in closet with enough room to feel like a small bedroom. Two additional guest bedrooms are located on the opposite side of the home, providing privacy for family or guests. These rooms can also easily be used as den, office, or flex spaces, with a conveniently located bathroom between them. The private in-law suite is accessed through its own separate entrance from the screened front walkway and includes a full bathroom, making it ideal for extended family, overnight guests, or a private retreat. Step outside to the screened and covered lanai, where you can relax and enjoy peaceful water and conservation views. It’s the perfect spot for morning coffee, entertaining, or simply enjoying the Florida lifestyle. The spacious two-car garage provides plenty of storage, along with a golf cart hookup and attic storage space. Additional benefits include windows, doors, and construction features designed to meet current hurricane-code standards, which will qualify the home for available new-home and hurricane-protection insurance discounts. The property is also NOT in a flood zone (Zone X). This exceptional Calabria model combines a desirable floor plan, private in-law suite, beautiful views, abundant storage, and a fantastic location near the Village Amenities Center. A must-see home that truly feels like new! The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

163 Olympus Way, Kissimmee
$438,020
4 Beds ⋅ 3 Baths ⋅ Knightsbridge 50s SubDv. ⋅ 34746 Zip Code
Under Construction. The Providence is a palatial two-story home with four bedrooms and two and a half bathrooms. The first floor features a family room for shared moments, a dining room for memorable meals, a kitchen for adventurous cooks, a flex room for versatile uses and a patio for outdoor living. There is a spacious loft upstairs that adds shared living space, in addition there are four bedrooms. The Owner Suite features a large walk-in shower, dual vanity, and spacious walk-in closet. Lennar has reimagined the homebuying experience by including the most desired home features at no extra cost to you. All features and products can vary by community and homesite. Knightsbridge residents enjoy access to outdoor amenities including a swimming pool & cabana, playground, volleyball court and walking trail. Enjoy local dining and shopping from downtown Kissimmee. Close to Lake Toho if you like to boat or walk the lakefront. Conveniently located near Walt Disney World and major Osceola County attractions.

5234 Worchester Drive, Kissimmee
$379,900
3 Beds ⋅ 2 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Welcome home! This well-maintained property is located in the desirable Kindred community of Kissimmee and features a thoughtfully designed floor plan that makes excellent use of the living space. The open layout creates a natural flow between the main living areas, offering comfortable spaces for everyday living and entertaining, while the bedrooms provide privacy and flexibility. Step outside and enjoy the screened porch, perfect for relaxing and enjoying the Florida lifestyle. Ideally situated within walking distance of the community clubhouse and school, this home puts everyday convenience close at hand. Enjoy all that Kindred has to offer, including resort-style amenities such as swimming pools, a fitness center, playgrounds, sports courts, walking trails, and more. Conveniently located with easy access to shopping, dining, major roadways, and everything Central Florida has to offer. A wonderful opportunity to enjoy a comfortable home in a vibrant, amenity-rich community!

1702 Walnut Crk Drive, Kissimmee
$875,000
4 Beds ⋅ 4 Baths ⋅ Celebration Area 5 SubDv. ⋅ 34747 Zip Code
First floor primary bedroom plus upstairs ensuite in desirable Artisan Park. This charming 4-bedroom, 3.5-bath Coastal-style with 2,587 square feet of living space, this home features double front porches and a floor plan designed for comfortable everyday living. The primary suite is conveniently located downstairs, while three additional bedrooms are upstairs, including one with a private bathroom. As you enter the home, you're greeted by a separate dining room and living room, creating a welcoming and traditional entry space. As you continue toward the back of the home, the layout opens into the kitchen and family room, creating a comfortable gathering space for everyday living. The backyard patio provides a great spot for outdoor dining and entertaining, or simply relaxing and enjoying the Florida weather. The home also features fully owned solar panels and a new roof was installed in 2022. Residents of Artisan Park have exclusive access to the private clubhouse, featuring a restaurant and bar, fitness center, and resort-style pool, along with a variety of social events held throughout the month.

1114 Tapestry Drive, Celebration
$540,000
3 Beds ⋅ 3 Baths ⋅ Esplanade At Westview SubDv. ⋅ 34758 Zip Code
What's Special: Larger Lot | Flex Room | Pond View | Gourmet Kitchen. New Construction – Ready Now! Welcome to the Ambra at 5676 Nevis Terrace at Esplanade at Westview! The open-concept living area seamlessly connects the great room, spacious kitchen with a large center island, and views of the covered lanai, creating an inviting space for everyday living and entertaining. A formal dining room is conveniently located near the kitchen for special gatherings. At the back of the home, two private primary suites each feature a walk-in closet and en-suite bathroom. A secondary bedroom and full bathroom are situated at the front of the home, while a spacious laundry room just off the garage entry adds everyday convenience. Additional Highlights Include: a bay window in the primary bedroom, a bay window in the second primary bedroom, gourmet kitchen, tray ceiling package, 8' interior doors, and laundry room sink. Photos are for representative purposes only. MLS#O6432452 Experience resort-style living at Esplanade at Westview in Kissimmee! Enjoy a resort-style pool, Bahama Bar, private cabanas, fitness center, tennis, pickleball, and bocce courts. Relax with spa services, gather around the firepit, or visit the Bark Park with your pup. This thoughtfully designed community offers endless opportunities to stay active, social, and refreshed. Conveniently located near BridgePrep Academy of Osceola charter school.

5676 Nevis Terrace, Kissimmee
$770,000
3 Beds ⋅ 3 Baths ⋅ Esplanade At Westview SubDv. ⋅ 34758 Zip Code
What's Special: Covered Extended Lanai | Pond View | Oversized Garage. New Construction - Model Home Available Now! Welcome to the Pallazio at 4364 Curacao Place in Esplanade at Westview! Blending elegant design with everyday comfort, this thoughtfully crafted home offers a spacious open-concept layout centered around a stunning great room, gourmet kitchen, and casual dining area that flow seamlessly to an expansive outdoor living space. The private primary suite serves as a peaceful retreat, while two secondary bedrooms, a versatile flex room, and formal dining space provide flexibility for work, hosting, or relaxation. With abundant natural gathering spaces and inviting details throughout, this home is designed to make every day feel warm, effortless, and beautifully connected. Additional Highlights Include: upgraded appliance package, 4-foot garage extension and paved back yard. MLS#O6432402 Experience resort-style living at Esplanade at Westview in Kissimmee! Enjoy a resort-style pool, Bahama Bar, private cabanas, fitness center, tennis, pickleball, and bocce courts. Relax with spa services, gather around the firepit, or visit the Bark Park with your pup. This thoughtfully designed community offers endless opportunities to stay active, social, and refreshed. Conveniently located near BridgePrep Academy of Osceola charter school.

4364 Curacao Place, Kissimmee
$279,000
1 Beds ⋅ 1 Baths ⋅ Siena At Celebration Condo B SubDv. ⋅ 34747 Zip Code
Virtually Staged. A beautifully maintained condo located within the Siena Condominium Association in Celebration, FL. This spacious one-bedroom, one-bathroom with a den residence features 1,057 square feet of thoughtfully designed living space. This property is ideal for those seeking both comfort and functionality. The interior is highlighted with luxury vinyl flooring throughout, providing a modern and low-maintenance touch to the space. This open floor plan offers plenty of Natural Light that features a living room, dining room, an open kitchen with breakfast bar and a separate den/office for those whom work from home The Spacious 13' x 11' Bedroom/Bath features a walk-in closet and a single vanity with Tub/Shower Combo. Newer Luxury Vinyl Flooring, Range & Microwave. The Siena Condominium Association also provides access to fantastic amenities, including a sparkling pool perfect for relaxing or soaking up the Florida sunshine. Additionally, residents can stay active and healthy with the well-appointed Fitness Center, Social Room, and Playground. Enjoy the Celebration Lifestyle with shops, restaurants, heated community pool, basketball & tennis courts, and Nature Trails.

714 Siena Palm Drive Unit 104, Celebration
$359,000
3 Beds ⋅ 3 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Well you can stop looking You found this gem, this spectacular 3 bedroom 2 half bath in the very Desirable subdivision of Kindred this particular unit is facing a beautiful park with the playground and walking trails You will enjoy second floor loft and love open concept on your on your first floor and get ready to live the resort style living with not one two but three pools but also three fitness centers that are there for your convenience Let's not talk about the tennis courts volleyball court and all that Kindred has to give to their residences With its 5 miles of trails for walking jogging Biking and let's not forget about the doggy park Or the soccer field So much to do to enjoy the Florida lifestyle living and so much is coming to this beautiful resort style subdivision And with a 5-10 minute drive to plenty of shopping And all kind of delicious restaurants You definitely won't be disappointed Come and put this one on your LIST This subdivision is centrally located 2 the Florida Turnpike the 417 and the 528 And only about a 25 minute drive to Orlando's International Airport And let's not forget all the theme parks

1854 Katz Crossing Drive, Kissimmee
$590,000
7 Beds ⋅ 5 Baths ⋅ Emerald Island Resort SubDv. ⋅ 34747 Zip Code
Welcome to Emerald Island Resort, a gated and guarded vacation community located just minutes from Walt Disney World! This property has a very good rental history, ($81,080.40 in 2025) & ($60,097.00 ytd in 2026). This spacious 7-bedroom, 4.5-bathroom home offers the perfect combination of a turnkey short-term rental investment, second home, or full-time Florida residence. Situated on a private conservation lot, the home features a large south-facing heated private pool and spa, extended sundeck, spacious covered lanai, and peaceful conservation views. The open floor plan includes a large kitchen with island, granite countertops and stainless steel appliances, three king-size bedroom suites, themed bedrooms, and a garage converted into a fully air-conditioned game room. The home is being sold fully furnished and is ready for immediate use or continued vacation rental operation. For investors, the property offers the opportunity to assume the existing future bookings, representing upwards of $30,000 in rental revenue, providing an immediate head start for the new owner. Recent improvements include a roof replacement in 2022, a full interior and exterior paint refresh in 2023, resolution of a prior A/C issue in 2026, and a newly replaced pool pump and air blower. Additional features include laminate flooring, updated window treatments, pool/spa heater, and updated upstairs and downstairs A/C systems. Emerald Island Resort offers an exceptional location and resort lifestyle, surrounded by conservation areas and conveniently located near Disney, restaurants, shopping and Central Florida’s major attractions. Owners and guests enjoy access to an impressive array of amenities, including a clubhouse, sauna, fitness center, resort pools and spas, food court and bar, tennis, basketball, volleyball, miniature golf, children’s play areas, walking trails and more. The clubhouse is approximately a 7-minute walk from the home. Whether you’re looking for a proven vacation rental opportunity, a family retreat, or a permanent Florida residence, this beautifully maintained and fully furnished home offers flexibility, privacy, resort amenities and an unbeatable location near the area’s world-famous attractions. Schedule your private showing today!

8452 Secret Key Cove, Kissimmee
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