Kissimmee Homes with Trail(s) Amenities

Kissimmee Homes with Trail(s) Amenities

Welcome to Kissimmee, a charming city located in Osceola County, Florida. Known for its picturesque landscapes and vibrant community, Kissimmee offers residents a perfect blend of suburban tranquility and urban convenience.

One of the standout features of homes in Kissimmee is the Trails Amenities. Imagine living in a community where you can enjoy leisurely strolls or invigorating runs along beautifully landscaped trails. These trails not only provide a scenic backdrop for your daily exercise routine but also offer a great way to connect with nature and unwind after a busy day.

Whether you're a nature enthusiast, fitness buff, or simply enjoy the outdoors, homes with trail amenities in Kissimmee are sure to appeal to your lifestyle. From morning jogs to evening walks with your furry friends, these trails provide the perfect setting for you to stay active and enjoy the fresh air.

With easy access to shopping, dining, entertainment, and major highways, Kissimmee offers the perfect balance of convenience and serenity. Whether you're looking for a cozy townhouse, a spacious single-family home, or a luxurious estate, Kissimmee has a diverse range of real estate options to suit your needs.

Experience the beauty and convenience of living in Kissimmee, where homes with trail amenities offer a unique opportunity to embrace an active and fulfilling lifestyle in a welcoming community.

Newest Kissimmee Homes with Trail(s) Amenities

$360,000
3 Beds ⋅ 2 Baths ⋅ Remington Prcl G Ph 2 SubDv. ⋅ 34744 Zip Code
Golf-course investment opportunity in Remington. This well-positioned three-bedroom, two-bath single-family home offers approximately 1,816 square feet of living area, a new roof installed in 2026, direct golf-course views and a covered rear lanai. The property is currently leased at $1,925 per month through February 28, 2027 and is being offered subject to the existing lease. Remington community amenities include golf, recreation facilities, pool, tennis courts and walking trails, subject to HOA confirmation. Conveniently located near Florida’s Turnpike, shopping, schools and dining. Seller will consider up to $5,000 toward buyer closing costs with an acceptable offer, subject to contract terms and lender approval. Property is being sold as-is with the buyer’s right to inspect.

119 Southampton Drive, Kissimmee
$415,000
3 Beds ⋅ 3 Baths ⋅ Creekside At Boggy Creek Ph 1 SubDv. ⋅ 34744 Zip Code
Virtually Staged. Why wait to build when you can move right into this 2019 BUILT home in the GATED COMMUNITY of Creekside at Boggy Creek! Offering the perfect blend of space, style and energy efficiency, this 3-bedroom, 2.5-bath home features ***PAID-OFF SOLAR PANELS***, saving you money while adding long-term value. Just minutes from Lake Nona, this home also boasts a private FENCED BACKYARD, attractive landscaping, a paver driveway and fantastic curb appeal. Inside, TILE FLOORING flows throughout the main level where an OPEN CONCEPT living, dining and kitchen layout is filled with natural light, creating an inviting space for everyday living and effortless entertaining. The chef-inspired kitchen showcases granite countertops, STAINLESS STEEL APPLIANCES, pendant lighting, a large center ISLAND with seating and a spacious pantry. Sliding glass doors extend the living space to a COVERED LANAI overlooking the privacy-fenced backyard – perfect for relaxing, pets or weekend gatherings. Upstairs, a generous BONUS/LOFT offers flexible space for a media room, home office or playroom. All three bedrooms are thoughtfully located on the second floor, including your PRIMARY SUITE with twin windows that fill the room with natural light, a WALK-IN CLOSET and a dedicated en-suite bath. Two additional bedrooms share a full bath, and the conveniently located second-floor laundry room makes everyday chores a breeze. Wood laminate flooring enhances the primary bedroom and one secondary bedroom. Residents of Creekside at Boggy Creek enjoy a gated entrance, COMMUNITY POOL and playground just four homes away, plus an unbeatable location with quick access to Boggy Creek Road, Narcoossee Road, SR 417, shopping, dining, parks, lakes and all the conveniences of the thriving Lake Nona area. Zoned for “A-RATED” Narcoossee Middle School, this home delivers the lifestyle, location and features you have been searching for. Call today to schedule a tour ~ WELCOME HOME!

4366 Silver Creek Street, Kissimmee
$424,990
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code
The Harper floorplan offers a 4-bedroom, 2-bathroom home with 1,665 sq ft of living space. Features include quartz and Revwood floors, an open layout, a spacious living room with natural light, a chef's kitchen with quartz countertops and stainless steel appliances, and a primary suite with a private ensuite bathroom. This all concrete block construction home also includes smart home technology for control via smart devices. *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.*

1856 Howard Mesa Drive, Kissimmee
$439,995
4 Beds ⋅ 2 Baths ⋅ Villa Sol Ph 02 Village 03 SubDv. ⋅ 34744 Zip Code
WELCOME TO 3028 CAMINO REAL DR S – YOUR PRIVATE POOL HOME IN THE UPSCALE GATED COMMUNITY OF VILLA SOL! Welcome to this beautiful pool home offering the perfect blend of comfort, privacy, and resort-style living in one of Kissimmee's most desirable communities. Whether you're searching for your primary residence, a vacation home, or an investment opportunity, this move-in-ready property checks all the boxes. Step inside to a spacious, open-concept floor plan filled with natural light, featuring generous living and dining areas that are perfect for everyday living and entertaining. The well-appointed kitchen offers ample cabinet and counter space and overlooks the main living area, making it ideal for gatherings. The spacious primary suite serves as a private retreat with a walk-in closet and en-suite bathroom, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your private screened-in pool, where you can relax, entertain, or enjoy Florida's year-round sunshine in your own backyard oasis. Located in the highly sought-after Villa Sol gated community, residents enjoy resort-style amenities including a clubhouse, community pool, fitness center, tennis courts, playground, walking trails, and beautifully maintained grounds. Conveniently located just minutes from Lake Nona Medical City, Orlando International Airport, SR-417, Florida's Turnpike, shopping, dining, golf courses, and world-famous attractions including Walt Disney World, Universal Orlando, and SeaWorld. Don't miss this incredible opportunity to own a private pool home in an unbeatable location. Schedule your private showing today before it's gone!

3028 Camino Real Drive S, Kissimmee
$490,990
5 Beds ⋅ 3 Baths ⋅ Kindred Ph 2a 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.*

1519 Beechmont Drive, Kissimmee
$344,400
2 Beds ⋅ 2 Baths ⋅ Tohoqua Ph 5a SubDv. ⋅ 34744 Zip Code
Beautiful meticulously maintained Villa in a 55+ gated community, Tohoqua Reserve. This move-in ready home features lots of upgrades. This spacious 2-bedroom, 2-bathroom home features a versatile bonus/flex room, perfect for an office, or can be easily converted into a third bedroom. Upon entering the home, you'll notice the beautiful crown molding throughout the home, and an abundance of natural light filling the living space. The open floor plan combines the kitchen, dining, and living areas, creating a beautiful open, bright and welcoming space. The kitchen features lots of storage space, a pantry, gray cabinets, quartz countertops, an island, and stainless-steel appliances. Through the triple sliding glass doors is a screened-in covered lanai, with extended pavers and artificial grass, perfect for relaxation. The large main bedroom offers a bathroom with a dual sink vanity, tile shower, linen closet, and a large walk-in closet. The 2-car garage features an upgraded epoxy floor for improved durability and sleek appearance. This community offers excellent recreational amenities, including access to 2 resort-style pools, clubhouse, tennis, pickleball courts, bocce ball court, fire pits, fitness centers, playground, and miles of outdoor scenic walking trails. Tohoqua Reserve is conveniently located near US-192 and the FL Turnpike and is within 30 minutes of Orlando International Airport and Disney World. Lots of shopping centers nearby and close to the beautiful Saint Cloud Lakefront area.

1845 Spring Shower Circle, Kissimmee
$480,990
5 Beds ⋅ 3 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code
Under Construction. Inside this beautiful 5-bedroom, 3-bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances. You'll never be too far from the action with the living and dining area right there. Find RevWood Select Flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. The primary bedroom has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Privacy is guaranteed with a separate door for the toilet and shower. *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.*

1527 Beechmont Drive, Kissimmee
$394,990
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.*

2042 Walnut Creek Drive, Kissimmee
$446,990
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.*

1539 Beechmont Drive, Kissimmee
$388,500
3 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 4b SubDv. ⋅ 34744 Zip Code
Welcome to this beautifully maintained Pulte-built bungalow in the highly desirable Tohoqua community. Built in 2023, this move-in ready home offers 2,072 square feet of thoughtfully designed living space featuring 3 bedrooms, 2.5 bathrooms, a spacious loft, and a rear-entry 2-car garage. A charming covered front porch welcomes you into a bright and inviting open-concept floor plan designed for both comfortable everyday living and effortless entertaining. The main level features tile flooring throughout the living areas, abundant natural light, and seamless flow between the living room, dining area, and kitchen. The kitchen serves as the heart of the home, showcasing white shaker cabinetry, quartz countertops, stainless steel appliances, a large center island with seating, stylish pendant lighting, and ample storage space. All kitchen appliances, along with the washer and dryer, are included for the new owner. Upstairs, an oversized loft provides flexible space ideal for a second living area, media room, home office, fitness area, or playroom. The spacious primary suite features a large walk-in closet and a private ensuite bathroom with dual vanities and quartz countertops. Two additional bedrooms share a full bathroom, while a convenient half bath is located on the first floor for guests. Additional highlights include ceiling fans, window blinds throughout, Ring doorbell, tile flooring throughout the main living areas, well-maintained carpeting upstairs and on the staircase, and a rear-entry 2-car garage with additional driveway parking for two more vehicles. Perfectly positioned facing a beautifully landscaped green space with sidewalks and pedestrian-friendly walkways, this home offers a peaceful setting without direct traffic immediately in front of the property, creating a more private and welcoming environment. Residents of Tohoqua enjoy outstanding community amenities, including multiple resort-style swimming pools, cabanas, a recently opened clubhouse and pool area, tennis courts, passive parks, playgrounds, walking trails, and beautifully maintained common areas designed to promote an active and connected lifestyle. Conveniently located near schools, shopping, dining, and everyday conveniences, this exceptional home combines modern construction, functional living spaces, and outstanding value in one of Osceola County’s most sought-after newer communities.

1959 Summer Serenity Drive, Kissimmee
$429,900
5 Beds ⋅ 3 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Welcome to your dream home in the highly sought-after Kindred community! This beautiful 5-bedroom, 3-bathroom home offers a thoughtful layout with a first-floor bedroom and full bathroom, perfect for guests, multi-generational living, or a private home office. Enjoy the comfort and the elegance of NO CARPET on the first floor. Stroll directly to the clubhouse, pool, and community amenities, or explore the scenic walking trails, sidewalks, and open green spaces throughout the neighborhood. Families will love the convenience of a K-8 school right in Kindred, while commuters will appreciate being just **10 minutes from the Florida Turnpike, 20 minutes to Downtown Kissimmee, and 30 minutes to Disney’s world-famous theme parks**. Life in this vibrant community feels like a year-round vacation. Residents enjoy multiple pools, a brand-new clubhouse, a fitness center, recreational fields, a pet park, beach volleyball courts, walking and biking trails, and playgrounds. Relax under shaded cabanas, gather with friends in open green spaces, or stay active at the outdoor exercise stations, all designed to support a healthy, social, and community-focused lifestyle. This home also offers an UNBEATABLE location with easy access to US-192, SR-417, and Florida’s Turnpike, putting NeoCity, Lake Nona/Medical City, Orlando International Airport, and world-class theme parks just minutes away. Combining comfort, convenience, and lifestyle, this is a home you don’t want to miss!. Schedule your showing today and make it yours!

1591 Barberry Drive, Kissimmee
$409,990
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Allex. This all concrete block constructed, one-story layout optimizes living space with an open concept. As you go down the hallway and enter a spacious kitchen featuring stainless steel appliances with ample counter space and a walk-in pantry for extra storage. The living room is complete with a view to the covered lanai outside. Bedroom one, located at the back of the home for privacy, has an en suite bathroom that features a double vanity sink with a walk-in closet. Two additional guest bedrooms and one bath are tucked away down the hall from the dining room. The laundry room is located at the front of home near the two-car garage. Like all homes in Kindred, the Allex 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.*

1872 Howard Mesa Drive, Kissimmee
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