Kissimmee Homes with Trail(s) Amenities

Kissimmee Homes with Trail(s) Amenities

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the charm of small-town living with the excitement of nearby attractions. Nestled in the heart of Central Florida, Kissimmee is just a stone's throw away from the world-renowned Walt Disney World Resort, Universal Studios, and an array of other theme parks, making it an ideal location for families and adventure seekers alike.

Kissimmee boasts a rich tapestry of cultural experiences, outdoor activities, and community spirit. With its picturesque lakes, lush parks, and scenic trails, residents can enjoy a plethora of recreational opportunities right at their doorstep. The city's historic downtown area features quaint shops, delightful dining options, and local events that foster a strong sense of community.

For those seeking homes in Kissimmee, you’ll be delighted to discover properties that come equipped with exceptional trail amenities. Many neighborhoods in this area offer beautifully maintained trails perfect for walking, jogging, or biking. Imagine starting your day with a refreshing morning stroll along a scenic path, surrounded by nature, or enjoying a leisurely bike ride with family and friends. These trails not only promote an active lifestyle but also provide a serene escape from the hustle and bustle of daily life.

Whether you’re looking for a cozy single-family home or a spacious townhouse, Kissimmee’s real estate market has something for everyone. Embrace the vibrant lifestyle that Kissimmee offers, where adventure meets tranquility, and make this enchanting city your new home!

Newest Kissimmee Homes with Trail(s) Amenities

39 Chip Court, Kissimmee

39 Chip Court, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Poinciana Village 01 Neighborhood 03 South SubDv. ⋅ 34759 Zip Code

Virtually Staged. Welcome to 39 Chip Court, a beautifully maintained 4-bedroom, 2-bath single-story home located in the Poinciana community of Kissimmee. Freshly painted inside and out, this inviting home offers a bright, spacious layout with tile flooring, updated appliances, and comfortable living areas designed for everyday living and entertaining. The kitchen flows seamlessly into the main living spaces, creating an open and welcoming atmosphere. All four bedrooms are conveniently located on one level, offering the ease and practicality of single-story living. Step outside to the expansive screened-in lanai, a wonderful extension of the home with plenty of room to relax, entertain, or enjoy Florida's year-round sunshine. Residents of Poinciana enjoy access to community amenities, including pools, parks, playgrounds, fitness and community centers, and recreational facilities. Conveniently located near shopping, dining, and everyday essentials, with Walt Disney World and the greater Orlando area's attractions within driving distance. With its fresh updates, functional layout, and spacious outdoor living area, 39 Chip Court offers a wonderful opportunity to enjoy the Central Florida lifestyle. Schedule your private showing today!

39 Chip Court, Kissimmee

5065 Worchester Drive, Kissimmee

5065 Worchester Drive, Kissimmee

5 Beds ⋅ 3 Baths ⋅ Knightsbridge 50s SubDv. ⋅ 34746 Zip Code

Under Construction. The two-story Durham is the largest plan in this collection and features an open space living room, along with an airy flex space perfect for an office or den. There is a private owner’s suite on the first floor with a spa inspired owner bath and fabulous walk-in closet. Upstairs is a spacious loft for an extra common area, along with four comfortable bedrooms. At the front is flex space for versatile needs and a desirable two-car garage. 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. It is conveniently located near Walt Disney World and major Osceola County attractions.

5065 Worchester Drive, Kissimmee

1894 Cassidy Knoll Drive, Kissimmee

1894 Cassidy Knoll Drive, Kissimmee

5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code

Virtually Staged. Welcome to 1894 Cassidy Knoll, an exceptional home in the highly sought-after Kindred community featuring one of the largest and most desirable floor plans ever offered in the neighborhood. No longer available from the builder, this expansive design is known for its generously sized rooms, outstanding functionality, and flexible living spaces. The enormous first-floor primary suite offers exceptional privacy and convenience, complete with a massive walk-in closet and a unique, code-compliant doorway providing direct access to the garage. This thoughtful upgrade allows homeowners to come and go without disturbing the rest of the household. The home also features another spacious bedroom with a private en-suite bathroom, ideal for guests or multigenerational living, along with a versatile flex room that could serve as a formal dining room, home office, or potential sixth bedroom. What truly separates this home from others in Kindred is the extensive investment in aftermarket upgrades. The backyard features a massive 44-by-15-foot professionally installed paver lanai, offering approximately 660 square feet of outdoor entertaining space. A newly fenced backyard and a 7-by-7-foot shed/workshop, which conveys with the property, provide even more functionality. Inside, all carpeted areas have been replaced with premium luxury vinyl plank flooring. Exterior improvements include a widened driveway designed to accommodate larger vehicles and a paver walkway connecting to the driveway. The garage is equally impressive, featuring epoxy flooring, multiple 220-volt outlets suitable for electric vehicle charging equipment, a granite-topped utility sink, and additional washer and dryer hookups. While the main laundry room is upstairs, the garage provides the flexibility for a second laundry area. Two separate garage access points and a newer whole-home water softener and filtration system add even more convenience. Kindred offers an outstanding location just minutes from Florida's Turnpike, allowing residents to bypass much of the congestion along US 192. Shopping, dining, and everyday conveniences are nearby, while Walt Disney World is approximately 25 to 30 minutes away. The community also features its own K-8 school and resort-style amenities, including a swimming pool, clubhouse, fitness center, tennis courts, and basketball courts. A future commercial section is also planned within the community. With its rarely available floor plan, oversized bedrooms, first-floor primary suite, incredible outdoor entertaining space, and extensive upgrades, 1894 Cassidy Knoll offers a combination of size, comfort, and functionality that is increasingly difficult to find in today's new construction.

1894 Cassidy Knoll Drive, Kissimmee

1859 Beach Ridge Rd, Celebration

1859 Beach Ridge Rd, Celebration

4 Beds ⋅ 4 Baths ⋅ Celebration Island Village Ph 1b SubDv. ⋅ 34747 Zip Code

Prof Photos Coming Soon! Luxury, technology & resort-style living come together beautifully in this highly upgraded SANIBEL COASTAL by Mattamy Homes, ideally positioned on a **PREMIUM CONSERVATION HOMESITE** offering a peaceful natural backdrop & enhanced privacy. Featuring 4 bdrms,3.5 bths,approx 3,499 sq ft & a 3-car tandem garage,this exceptional home has been thoughtfully designed for both everyday living and entertaining.The open-concept kitchen,dining area & Great Room are complemented by a 1ST-floor Owner’s Suite, private 1ST-floor Guest Suite,versatile Flex Room with double glass doors, & an upstairs Loft with 2 additional bedrooms and shared bath.The impressive kitchen showcases ceiling-height upgraded cabinetry with soft-close doors & drawers,quartz countertops,a designer island sink & combination oven/microwave Luxury vinyl plank flooring flows throughout the home,complemented by upgraded bathroom tile,8-foot interior doors,enhanced trim & extensive LED lighting.Sound-barrier insulation was added to interior walls on both levels for enhanced comfort & privacy.The 1st-floor Owner’s Suite offers a spa-inspired retreat with an upgraded freestanding soaking tub,spacious walk-in shower,ceiling-height cabinetry & designer tile finishes.The Flex Room provides an ideal home office or additional guest space & includes a queen-size Murphy bed concealed within the closet.Step outside to your own private Florida resort,beautifully complemented by the *conservation setting beyond the backyard*. The spectacular outdoor living area features an EASY TO MAINTAIN luxury pool, that automatically fills & drains to maintain water levels & includes a waterfall spa,deck jets & sun shelf, all surrounded by a full screen enclosure.Entertain from the outdoor kitchen,practice your short game on the private PUTTING GREEN,or simply relax among tropical landscaping & accent landscape lighting.The backyard is fully fenced for privacy.Technology is integrated throughout the home,including Cat 6A Ethernet wiring,whole-home Wi-Fi access points,5.1 surround sound in the Great Room with speakers extending to the lanai,security cameras & video doorbell.Smart-phone control is available for the pool & spa,HVAC,garage doors,irrigation,security system & select exterior lighting.Programmable automated Levolor blinds enhance the front windows, & the garage is prewired for an EV charger.Fiber internet service.Additional upgrades include a Pure Touch water filtration system & water softener,ceiling fans,gutters,whole-home electrical surge protection,upgraded closet & pantry shelving,wall shelving,TV wall mounts & termite protection.The 3-car tandem garage provides excellent vehicle & storage space. This is far more than a builder-standard home.The *premium conservation homesite*, extensive upgrades, advanced technology & thoughtfully designed indoor/outdoor living spaces combine to create an exceptional move-in-ready property where luxury Florida living begins the moment you arrive. Located in Island Village, the latest development within the world-renowned community of Celebration; the town developed by Disney.Residents enjoy a host of amenities including Golf, Pools, Playgrounds,Tennis & Basketball, miles of biking/walking trails,several shopping & eating plazas along w/a charming Waterfront Downtown. Celebration sponsors a number of seasonal & holiday events along with a Sunday Farmer's Market. Close to Disney World,major roadways,medical services & so much more!

1859 Beach Ridge Rd, Celebration

1884 Southbury Drive, Kissimmee

1884 Southbury Drive, Kissimmee

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.*

1884 Southbury Drive, Kissimmee

1888 Southbury Drive, Kissimmee

1888 Southbury Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Under Construction. Inside this beautiful 4-bedroom, 3-bathroom home welcomes the Multi-Gen where you will find 2,077 square feet of comfortable living. The first Bedroom on the left has it’s own bathroom and sitting area with a kitchenette and a private entry to come and go as you please. 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 2 sink vanity. *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.*

1888 Southbury Drive, Kissimmee

2213 Wandering Oak Terrace, Kissimmee

2213 Wandering Oak Terrace, Kissimmee

4 Beds ⋅ 4 Baths ⋅ Oak Hammock Preserve Unit 1 SubDv. ⋅ 34746 Zip Code

Welcome to this beautifully upgraded 4-bedroom, 4-bathroom home offering 3,341 square feet of spacious, thoughtfully designed living space. From the impressive curb appeal and extensive landscaping to the long list of recent improvements, this home is truly move-in ready and designed for comfortable living, entertaining, and peace of mind. The welcoming interior features a formal living room and formal dining room, while the open-concept main living area brings together the family room, dining area, and beautifully appointed kitchen. The kitchen features an island and a convenient bar area, making it the perfect gathering space for family and guests. Under-cabinet lighting adds both style and functionality. The spacious primary suite provides a private retreat with a bathroom featuring dual vanities, a soaking tub, separate shower, and a generous walk-in closet. A large laundry room offers exceptional functionality with a built-in sink and counter space. Upstairs, a versatile bonus room with a full bathroom provides endless possibilities and can be used as a fifth bedroom, guest suite, home office, media room, or flex space. This home has been extensively updated with numerous improvements, including a new roof(2023) new carpet installed(2026). Interior and exterior paint were completed in 2026. For enhanced energy efficiency and comfort, the home features a main HVAC system(2026) with 20 SEER efficiency, HEPA filtration, and UV treatment, along with an 18 SEER upstairs HVAC system(2023) both with smart home thermostats. Additional efficiency features include a hybrid water heater, spray foam insulation at the roof deck, core-injection foam insulation in the cinder block walls, and tinted windows. A major highlight is the 25kW whole-house generator, recently serviced and designed to automatically activate during a power outage to keep the entire home running. The generator is supplied by an underground LP tank, which also provides a dedicated gas line to the rear deck for connection to an outdoor grill. Outdoor living is equally impressive. Enjoy the screened porch, additional paver patio, and inviting fire pit with built-in seating—an ideal setting for relaxing or entertaining. The beautifully maintained landscaping and excellent curb appeal create an inviting first impression. The garage is equipped with air conditioning, TV, insulation, a motorized privacy screen, and a new smart home garage door opener(2026). Additional features include a whole-house water softener, reverse osmosis system at the kitchen sink, upgraded irrigation controls installed in 2026, CCTV camera system, wired security system, and exterior security lighting. Located in a desirable community offering a pool, playground, and walking trails, this exceptional home combines space, comfort, extensive upgrades, energy efficiency, and thoughtful amenities. With so many major improvements already completed, this is an opportunity to enjoy a beautifully updated home without the hassle of taking on major projects.

2213 Wandering Oak Terrace, Kissimmee

2948 Penelope Loop, Kissimmee

2948 Penelope Loop, Kissimmee

6 Beds ⋅ 6 Baths ⋅ Cove At Storey Lake 4 SubDv. ⋅ 34746 Zip Code

Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details! | FULLY FURNISHED INVESTMENT OPPORTUNITY IN THE COVE AT STOREY LAKE! This spacious 6 bedroom, 6 bathroom pool home sleeps 16 people and offers an exceptional combination of resort-style living and a proven track record as a successful vacation rental. Future bookings are already scheduled and can be transferred to the new owner if the current management company is kept in place. Documentation indicates that OVER $130,000 IN GROSS RENTAL REVENUE has been generated in the last 12 months, providing an opportunity for rental income to start from day one. Designed to comfortably accommodate large groups, the home offers an abundance of living and entertaining space. The flexible floor plan features a theater with the addition of a bonus room downstairs which functions as a bedroom sleeping up to four and a spacious loft upstairs, providing multiple areas for guests to gather, relax, play, or entertain. Step outside to your own private Florida retreat featuring a paver lanai, screened pool and spa, and peaceful views of the conservation area behind the home. With no immediate rear neighbor, guests can enjoy additional privacy while relaxing poolside after a day at Central Florida's attractions. Located within The Cove at Storey Park, owners and guests enjoy access to an impressive collection of resort style amenities, including community pools, lazy river, hot tub, water slide, splash park, fitness center, basketball and volleyball courts, tiki bar, and more. Mini golf and kayaking are also available for an additional fee. The gated resort community provides 24-hour controlled access and is conveniently located near Walt Disney World, Universal Orlando, shopping, dining, grocery stores, and other Central Florida attractions. This property has a strong vacation rental history, boasting a guest rating of 4.92 out of 5 based on reviews. Whether you are looking for an income-generating vacation rental, a second home close to Orlando's attractions, or a spacious Florida retreat with resort-style amenities, this home offers the ideal combination for today's vacation home buyers.

2948 Penelope Loop, Kissimmee

4994 Town Terrace N, Kissimmee

4994 Town Terrace N, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Trafalgar Village Phase One SubDv. ⋅ 34758 Zip Code

Virtually Staged. Start your mornings with coffee overlooking the pond and end your days relaxing on your screened rear lanai. This three bedroom, three full-bathroom townhome in Trafalgar Village offers over 1,500 square feet of living space within a community featuring 24-hour guard gated access. Updated kitchen countertops, fresh interior paint, and fresh carpeting create a welcoming backdrop for your next chapter, whether you’re settling into a primary residence or creating a Florida getaway. Spend an afternoon by the community pool and spa, catch a movie at the clubhouse theater, or enjoy a game of pickleball, basketball, beach volleyball, or shuffleboard. A fitness center and game room with billiards and video games provide even more ways to unwind. Outdoors, discover a sandy beach area, scenic walking and jogging paths, a dog park, playground, and barbecue and picnic areas, all complemented by beautifully maintained common grounds and private community mailboxes. Low maintenance living adds to the appeal, with HOA coverage that includes lawn care, landscaping, trash service, roof, and exterior painting. Located in Kissimmee, Trafalgar Village offers access to shopping, dining, entertainment, and Central Florida’s celebrated theme parks, including Walt Disney World. With both short-term and long-term rentals permitted, this townhome offers the flexibility to enjoy it as your own home, a vacation retreat, or an investment property. Schedule your private showing and discover the possibilities.

4994 Town Terrace N, Kissimmee

770 Siena Palm Drive Unit 105, Celebration

770 Siena Palm Drive Unit 105, Celebration

2 Beds ⋅ 2 Baths ⋅ Siena At Celebration Condo A SubDv. ⋅ 34747 Zip Code

Welcome to Siena at Celebration, where low-maintenance living meets beautiful views and all the charm of one of Central Florida’s most beloved communities. This well-maintained 2-bedroom, 2-bathroom condo offers a the convenience of a ground floor location and single story, expansive layout. Step inside to a bright and welcoming interior where natural light fills the main living spaces. The kitchen is conveniently located near the entry and looks out toward the living and dining areas, making the space feel connected and inviting while still giving you the space to run your kitchen. A separate laundry room is located at the end of the kitchen, and the washer and dryer are included with the sale. French doors from the living and dining area open onto the private patio, framed with lush landscaping creating seclusion for the perfect spot to relax. The primary suite is tucked away on one side of the home and offers a comfortable retreat, a walk-in closet, and a private en-suite bathroom. The second bedroom is generously sized and located on the opposite side of the condo, offering privacy for guests or family members. It has direct access to the second full bathroom, which also opens to the main living area for convenient access when entertaining. Luxury Vinyl, wide plank flooring extends through the primary bedroom, living room, dining area, and second bedroom, while tile flooring is featured in the kitchen and bathrooms. Recent exterior improvements add even more peace of mind, with the building having been freshly painted and receiving a new roof. Siena at Celebration offers a resident exclusive resort-style pool, clubhouse, fitness center, and playground. And beyond the community itself, living in Celebration means enjoying an extensive collection of amenities, including six additional community pools, tennis and basketball courts, sand volleyball, sports fields for soccer, softball, and lacrosse, and more than 26 miles of scenic walking and biking trails. The location is equally appealing. Celebration’s vibrant downtown, with its restaurants, boutiques, lakes, and community events, is just minutes away. Celebration Pointe provides additional conveniences, including grocery shopping, dining, and a local brewery. Advent Health Celebration is nearby, while Walt Disney World is approximately 10 minutes away using World Drive as your access point, avoiding highway and I-4 traffic to the most magical place on earth. Orlando International Airport can be reached in roughly 25 minutes, and Florida’s Gulf and Atlantic coasts are both within easy reach for a day at the beach. With its peaceful views, thoughtful layout, and access to everything that makes Celebration such a special place to call home, this Siena condo offers a wonderful opportunity to enjoy the Celebration lifestyle with comfort and convenience.

770 Siena Palm Drive Unit 105, Celebration

3048 Boating Boulevard, Kissimmee

3048 Boating Boulevard, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Shingle Creek Reserve At The Oaks Ph 6 SubDv. ⋅ 34746 Zip Code

LOCATION, LOCATION, LOCATION! Bright and move-in ready 4-bedroom, 2.5-bath home in the highly sought-after Shingle Creek Reserve at The Oaks, with only one side neighbor and low HOA fees. Built in 2013 and meticulously maintained by its original owner (never rented), this home offers soaring ceilings, an open-concept layout, abundant natural light and NO CARPET throughout. KEY FEATURES: Main-floor primary suite, completely separated from the upstairs bedrooms. Main-floor flex room, ideal for a home office or reading area, PLUS a huge upstairs loft for recreation. Granite countertops in the kitchen and all bathrooms. A/C replaced in 2022. Screened lanai and spacious backyard. 2-car garage with two individual doors for independent vehicle access. Furnishings negotiable and available separately for a hassle-free transition. LAKE LIFESTYLE: Just cross the street to enjoy peaceful lake views! Community amenities include nature trails, green space, playground, basketball and tennis courts, picnic area and a boat ramp with access to Lake Toho. Minutes from Kissimmee dining, shopping and major highways. Schedule your private tour today!

3048 Boating Boulevard, Kissimmee

513 Heartwell Dr, Kissimmee

513 Heartwell Dr, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Solivita Ph Iib SubDv. ⋅ 34759 Zip Code

**SEE VIRTUAL TOUR LINK 1 FOR 3D MATTERPORT VIDEO** This beautifully maintained 2 BED, 2 BATH home (with loads of upgrades)in the premiere 55+ resort community of Solivita in Kissimmee, Florida, is FRESHLY PAINTED and ready for you to move in and start enjoying the Florida dream.Tucked on a quiet side street, yet near the Village Center, this popular Allegro model welcomes you with a screened front porch and leaded-glass entry. Inside, you’ll find ceramic TILE in the main living areas, GRANITE countertops in the kitchen, 42" upper cabinets, PULL OUT SHELVES in lower cabinets, a walk-in pantry, recessed lighting, 2 SKYLIGHTS, upgraded light fixtures, whole house SURGE PROTECTOR, and ceiling fans throughout. Both bathrooms feature granite counters and comfort-height commodes. Recent major updates include a new ROOF (2025), new HVAC (2025) with a 15 year transferable WARRANTY, newer Berber carpeting in the bedrooms and den, and newer water heater. Also NEW in 2025 - refrigerator, dishwasher and garbage disposal. The highlight is the expansive 35 X 10 screened lanai with Chattahoochee stone, RETRACTABLE AWNING, radiant heaters, ceiling fan, and enhanced privacy landscaping. Home is near one of the nicest ponds in Solivita with a walking path around it, and a neighborhood pool. See the full-length video tour to experience this move-in ready gem for yourself. Solivita offers an active adult lifestyle with championship golf, 14 heated pools, 17 pickleball courts, 9 tennis courts, 3 restaurants, miles of biking paths, over 250 clubs, and top-tier amenities. Located just 50 minutes from Disney World and Orlando International Airport, and directly across from the brand-new Poinciana Lakes Plaza with Sprouts, TJ Maxx, dining, and more. This is the sunshine-filled Florida life you’ve been waiting for!

513 Heartwell Dr, Kissimmee

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