Kissimmee Homes with Trail(s) Amenities

Kissimmee Homes with Trail(s) Amenities

Welcome to Kissimmee, Florida—a vibrant city that perfectly blends the magic of theme parks with the charm of small-town living. Nestled just south of Orlando, Kissimmee is renowned for its proximity to world-famous attractions like Walt Disney World, Universal Studios, and SeaWorld, making it a dream destination for families and adventurers alike. However, Kissimmee offers much more than just theme park excitement; it boasts stunning natural landscapes, rich cultural experiences, and a welcoming community spirit.

One of the most appealing aspects of living in Kissimmee is the abundance of homes with trail amenities. Imagine waking up to the gentle sounds of nature and stepping outside to find picturesque trails winding through lush greenery. These homes not only provide comfortable living spaces but also encourage an active lifestyle with easy access to walking, biking, and jogging paths. Whether you’re taking a leisurely stroll with your family, enjoying a morning run, or exploring the scenic vistas, the trails enhance your quality of life.

Kissimmee is a city that embraces outdoor activities, with numerous parks and recreational areas nearby. Residents can enjoy everything from fishing in serene lakes to picnicking in beautifully maintained parks. The blend of urban convenience and natural beauty makes Kissimmee a unique place to call home. With its warm climate, friendly neighborhoods, and homes that cater to an active lifestyle, Kissimmee is not just a place to live—it's a place to thrive. Discover your dream home here, where adventure awaits right outside your door!

Newest Kissimmee Homes with Trail(s) Amenities

$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
$399,000
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Welcome Home to Kindred living at its finest! Built in 2022, this move-in-ready, single-story home offers 4 spacious bedrooms, 2 full bathrooms, and 1,846 sq. ft. of open-concept living space. Step inside to discover a bright, airy floor plan featuring seamless flow between the living, dining, and kitchen areas—perfect for everyday living and effortless entertaining. The kitchen comes equipped with ample cabinetry, counter space, and a center island, overlooking the expansive living room filled with natural light. The primary suite serves as your private retreat, complete with a generous walk-in closet and an en-suite bathroom featuring dual sinks and a walk-in shower. Three additional bedrooms provide flexibility for family, guests, or a dedicated home office. Unbeatable Neighborhood Location: Situated on Park Side Ave, this home is conveniently located close to both the community Kindred K-8 school and Kindred’s main clubhouse complex, making daily routines and weekend relaxation effortless! Beyond the front door, experience the ultimate Florida lifestyle with Kindred’s resort-style amenities, including multiple community pools, splash pads, fully equipped fitness centers, sports courts (tennis and volleyball), miles of walking trails, tot lots, and a dedicated dog park. Prime Connectivity: Minutes from Neptune Road, US-192, and the Florida Turnpike for easy commuting. Conveniently located near NeoCity (Central Florida’s premier high-tech hub), Lake Tohopekaliga, Lake Nona, and Orlando International Airport (MCO). Schedule your private showing today and make this gorgeous Kindred home yours!

1735 Park Side Avenue, Kissimmee
$499,000
4 Beds ⋅ 3 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code
Welcome Home to Kindred living at its finest! Built in 2021, this impressive single-story home features 4 spacious bedrooms, 3 full bathrooms, over 2,100 sq. ft. of beautifully designed open-concept living space, and no rear neighbors! Step inside to an expansive floor plan boasting high ceilings and seamless flow between the living, dining, and chef’s kitchen areas. The open kitchen features modern finishes, a large center island, and plenty of cabinet storage—making it perfect for hosting guests or enjoying family meals. With a 3-full-bathroom layout, this floor plan offers exceptional convenience, ideal for multi-generational living, guests, or a private home office setup with its own dedicated bath. The primary suite serves as a tranquil retreat with a walk-in closet and a spa-like en-suite bathroom. Step outside to your own private backyard retreat with no rear neighbors, featuring a variety of bearing fruit trees including oranges, grapefruit, star fruit, ice cream bananas, and concord grapes. Unbeatable Neighborhood Location: Located directly on Park Side Ave, this home is within easy walking distance to the community Kindred K-8 Elementary school as well as Kindred’s main clubhouse, resort pool, and amenity complex—giving you effortless daily access right out your front door! Beyond the home, enjoy Kindred’s resort-style community amenities, including multiple pools, splash pads, fully equipped fitness centers, sports courts (tennis and sand volleyball), Soccer field, miles of walking trails, tot lots, and a dedicated dog park. Prime Connectivity: Minutes from Neptune Road, US-192, and the Florida Turnpike for smooth daily commutes. Conveniently located near NeoCity (Central Florida’s premier high-tech hub), Lake Tohopekaliga, Lake Nona, and Orlando International Airport (MCO). Schedule your private showing today to experience everything about this home and community!

1621 Park Side Avenue, Kissimmee
$315,000
3 Beds ⋅ 2 Baths ⋅ Maple Chase At Cypress Woods SubDv. ⋅ 34758 Zip Code
Rare find in this neighborhood. Nestled in the sought-after Maple Chase community within Cypress Woods Poinciana, this stunning 3-bedroom, 2-bathroom home offers 1,876 sq ft on a generous lot — complete with a tranquil water view and no immediate rear neighbors, giving you rare privacy and open space in your backyard. Inside, two living and dining room combinations offer ultimate flexibility — perfect for formal entertaining, a family gathering space, a playroom, or a home office. The spacious layout adapts effortlessly to your lifestyle, with vinyl flooring, and no carpets. The extra-large bedrooms set this home apart, offering ample space for king-sized furniture and room to truly unwind. Minutes from dining, shopping, major highways, and Walt Disney World — this home blends suburban tranquility with Central Florida convenience. Schedule your showing today!

4442 Maple Chase Trail, Kissimmee
$654,900
7 Beds ⋅ 6 Baths ⋅ Emerald Island Resort Ph 4 SubDv. ⋅ 34747 Zip Code
Turnkey short-term rental home, minutes to Disney! Discover a rare opportunity to own this stunning 7 bedroom, 6 bathroom pool home in the sought after Emerald Island Resort. Boasting the largest layout in the community at 3,667 sq. ft., this home is perfectly suited as a vacation getaway, income-generating investment, or forever family home. Enjoy unparalleled waterfront views framed by lush wooded backdrops, creating a serene and private retreat. The expansive screened lanai, which spans the length of the house, features a partially covered area ideal for year round entertaining. Relax by the sparkling South facing private pool and spa and take in the ultimate Florida lifestyle. Step inside to find a well designed floor plan with ample living space, ideal for families or hosting guests. The stylish kitchen is a chef’s dream with abundant cabinet and countertop space, a breakfast bar, and a breakfast nook overlooking the huge living room and pool, your new favorite spot for morning coffee or casual dining. The main floor also features two bedrooms, a formal dining room and the charming “Harry Potter” closet for extra fun and storage. The upper level is thoughtfully divided by two staircases. One leads to a loft sitting area and three themed bedrooms and the other leads to two additional themed bedrooms, all designed for comfort, as five of the bedrooms feature en-suite bathrooms, while the remaining two share a convenient Jack and Jill bath. The 3 car garage has been transformed into an entertainment haven with air conditioning, complete with a mini movie theatre (seating for 8) and a game room with a pool table. Updates include: A brand new roof (11/24), a new pool heater (04/24), newer exterior paint (01/22) and a newer A/C and heat pump (11/20), replumbed A/C lines (2024) and spa actuators replaced (2024). As part of this premier gated community, you’ll enjoy access to an impressive clubhouse with a resort-style pool, Tiki bar, fitness center, sauna, and sundry shop. Other amenities include tennis and pickleball courts, volleyball, basketball, bike rentals, and 11 acres of natural walking trails. The prime location is conveniently located near Orlando’s major attractions, including theme parks, outlet shopping, restaurants, Promenade at Sunset Walk, and Island H2O Live! water park. This home comes fully furnished and equipped with a strong rental history, ready to generate income as a short term rental or provide your family with a wonderful retreat. Schedule your tour today and experience the ultimate Florida lifestyle in this stunning property.

8557 La Isla Drive, Kissimmee
$4,495,000
4 Beds ⋅ 4 Baths ⋅ Celebration Village Unit 2 SubDv. ⋅ 34747 Zip Code
Welcome to Crescentwood, a truly rare offering in the Main Village of Celebration, a fully reimagined estate set across two homesites, creating a scale and presence seldom found within the community. Thoughtfully renovated with high-end materials and custom finishes throughout, the residence blends timeless architecture with modern luxury in a way that is both refined and highly livable. As you enter, the foyer welcomes you with substantial millwork, curated lighting, and a level of craftsmanship that immediately defines the residence. Formal and casual living spaces are elegantly proportioned, featuring beautiful tile flooring, layered ceiling details with integrated lighting, custom built-ins, French doors and oversized windows that fill the interiors with natural light. A beautiful sitting room framed by eight windows creates an inviting space bathed in natural light throughout the day. At the center of the home, the completely redesigned chef’s kitchen showcases custom Poggenpohl cabinetry, premium integrated appliances, dramatic illuminated stone surfaces, extensive preparation space, and a seamless connection to the adjacent living and dining areas, creating an ideal setting for both entertaining and everyday living. The owner’s suite serves as a luxurious private retreat with a spa-inspired bath finished in striking marble, custom fixtures, and refined architectural detailing. The suite is further enhanced by two walk-in closets, offering exceptional organization and boutique-style functionality. Each secondary bedroom are designed as private ensuite retreats complete with walk-in closets and beautifully updated bathrooms featuring elevated finishes and distinctive design details. The third-story movie room offers a true cinematic experience tucked away as a private entertainment space. Adding to the property’s versatility is a fully upgraded one-bedroom apartment featuring a private entrance, luxurious bath with a freestanding tub and separate shower, eat in space, living room and full-size washer and dryer offering ideal flexibility for guests, extended family or private office space. The main residence includes a two-car garage, while automotive enthusiasts and collectors will especially appreciate the separate temperature controlled oversized three-car garage. Designed with high ceiling height to accommodate vehicle lifts, the space has the potential to house up to six vehicles—an extraordinarily rare amenity within Celebration. The outdoor living experience is equally impressive, featuring a swimming pool and spa surrounded by elegant limestone pavers, summer kitchen, covered entertaining areas, and lush landscaping. A substantial stucco masonry wall encloses the grounds, creating an ultra-private backyard and pool setting rarely found within Celebration’s Main Village. Extensive landscape lighting beautifully illuminates the property and architectural details in the evening, enhancing the estate’s ambiance and presence after sunset. Multiple outdoor gathering spaces further elevate the estate-like atmosphere, creating the feel of a private luxury resort. Crescentwood represents a one-of-one opportunity within Celebration, offering the rarity of a double homesite, a fully renovated luxury residence and a level of finish and scale that is nearly impossible to replicate within the Main Village.

706 Golfpark Drive, Celebration
$444,000
5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Stunning Corner Lot Home with Exceptional Value! Don’t miss this incredible opportunity to own this spacious 5-bedroom, 3.5-bathroom home, priced below appraised value and offering up to $15,000 toward the buyer’s closing costs or rate buy-down. Designed with both comfort and functionality in mind, this beautiful home features a first-floor primary suite, providing privacy and convenience. The main level also includes a versatile flex room/den, perfect for a home office, playroom, study, or guest space. Upstairs, you’ll find a generous loft, ideal as a second living area, media room, game room, or entertainment space giving everyone room to relax and enjoy. Situated on a desirable corner lot, the property boasts a huge, fully fenced backyard with durable vinyl fencing, offering plenty of space for outdoor entertaining, pets, family gatherings, or even a future pool. With its spacious layout, premium corner location, oversized backyard, and outstanding buyer incentives, this home is an exceptional value that you won’t want to miss. Ask about available lender incentives toward buyer closing costs through select loan programs. Subject to lender approval and borrower qualification. Schedule your private showing today!

1876 Cassidy Knoll Drive, Kissimmee
$415,279
3 Beds ⋅ 2 Baths ⋅ Westview SubDv. ⋅ 34758 Zip Code
Under Construction. What's Special: Larger Lot | Covered Patio | Lake View | Spacious Kitchen. New Construction – October Completion! Built by America's Most Trusted Home Builder. Welcome to the Saint Thomas at 5772 Meads Bay Pond Road in Westview! A welcoming porch leads into an inviting foyer, where a private study offers the perfect space for working from home or pursuing hobbies. Beyond the foyer and rotunda, the heart of the home unfolds with a spacious great room, casual dining area, kitchen, and formal dining room thoughtfully connected for both everyday living and entertaining. Enjoy seamless indoor-outdoor living with a covered lanai overlooking the backyard. Tucked away for added privacy, the primary bedroom serves as a relaxing retreat and features two walk-in closets, an oval soaking tub, dual sink vanity, and walk-in shower. Two secondary bedrooms are situated off the rotunda and share a full bathroom, creating a comfortable space for family and guests. Welcome to Westview! Here, you can wake up to fresh morning air and the natural sounds of the outdoors in a thoughtfully planned community. You are surrounded by protected wetlands, forested uplands, ponds, open space, and miles of trails that invite you to explore right outside your door. Westview is ideally located near Poinciana Parkway in Kissimmee, Florida, placing you close to Lake Toho, Kissimmee Lakefront Park, Old Town, Walt Disney World, and more. This is a neighborhood where nature, convenience, and everyday adventure come together. Additional Highlights Include: a soaking tub with a separate shower in the primary bathroom, and a door into the primary bathroom. Photos are for representative purposes only. MLS#O6431007

5772 Meads Bay Pond Road, Kissimmee
$481,849
4 Beds ⋅ 4 Baths ⋅ Westview SubDv. ⋅ 34758 Zip Code
Under Construction. What's Special: No Rear Neighbors | Water View | Loft. New Construction - October Completion! Welcome to the Bermuda at 5766 Meads Bay Pond Road in Westview! This inviting two-story home blends comfort and functionality with a bright open-concept design. The spacious great room flows into the casual dining area and well-appointed kitchen featuring a large island and walk-in pantry. The first-floor primary suite offers a relaxing retreat with a spacious bathroom and walk-in closet, while a flex room near the foyer is perfect for a home office or hobby room. Upstairs, a versatile loft is accompanied by three secondary bedrooms and two full bathrooms. Enjoy outdoor living on the covered lanai, ideal for relaxing or entertaining. Welcome to Westview, a thoughtfully planned community surrounded by wetlands, ponds, open space, and miles of trails. Conveniently located near Poinciana Parkway, residents enjoy easy access to Lake Toho, Kissimmee Lakefront Park, Old Town, Walt Disney World, and more. Additional Highlights include: GE refrigerator, gourmet kitchen, and flush mount lighting package at great room. Photos are for representative purposes only. MLS#O6430976

5766 Meads Bay Pond Road, Kissimmee
$451,990
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2a 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.*

1503 Beechmont Drive, Kissimmee
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