Osceola Homes with Trail(s) Amenities

Osceola Homes with Trail(s) Amenities

Welcome to Osceola County, Florida – a vibrant and flourishing region that perfectly blends natural beauty with modern conveniences. Nestled in the heart of Central Florida, Osceola County is known for its stunning landscapes, rich cultural heritage, and a plethora of recreational opportunities. With its close proximity to the enchanting attractions of Orlando and the serene allure of the Kissimmee Chain of Lakes, Osceola County offers the best of both worlds – excitement and tranquility.

One of the standout features of this picturesque county is its commitment to outdoor living, particularly through homes that boast trail amenities. Imagine stepping out of your front door and finding yourself on a scenic trail, surrounded by lush greenery and the soothing sounds of nature. Many neighborhoods in Osceola County are designed with active lifestyles in mind, featuring well-maintained trails perfect for walking, jogging, or cycling. These trails not only promote a healthy lifestyle but also foster a sense of community, as residents come together to enjoy the great outdoors.

From charming single-family homes to luxurious estates, the real estate options in Osceola County are diverse and appealing. Whether you’re seeking a family-friendly neighborhood or a tranquil retreat, you’ll find a variety of homes that cater to your needs – all with the added benefit of easy access to the beautiful trails that wind through the area.

Discover the enchanting lifestyle that Osceola County has to offer, where nature and community come together in perfect harmony. Your dream home with trail amenities awaits!

Newest Osceola Homes with Trail(s) Amenities

$388,989
4 Beds ⋅ 2 Baths ⋅ Shores SubDv. ⋅ 34771 Zip Code
This thoughtfully designed, single-story home showcases an open floor plan with plush carpeting and a spacious great room that boasts soaring ceilings. Enjoy the convenience of a dedicated laundry room for everyday ease. The modern kitchen is equipped with a sleek wet island, laminate countertops, 42-in. upper cabinets, a Moen® faucet, a Kohler® stainless steel sink and Whirlpool® stainless steel appliances. Relax in the private primary suite, which features a large walk-in closet and luxurious connecting bath that offers a dual-sink vanity, linen closet and garden tub. Step outside to the covered back patio, which is perfect for enjoying peaceful mornings and vibrant gatherings.

2523 Plover Street, St Cloud
$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 Creek 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
$374,990
3 Beds ⋅ 3 Baths ⋅ Center Lake On The Park SubDv. ⋅ 34771 Zip Code
Under Construction. Discover this stunning new construction home located at 5192 Center Lake Ranch Blvd in St Cloud, FL. Built by M/I Homes, this thoughtfully designed townhome offers 1,833 square feet of comfortable living space perfect for today's lifestyle. This home features 3 spacious bedrooms, 2 full bathrooms and a powder room, an open-concept layout that seamlessly connects the main living areas, a courtyard, and a 2-car garage. The home's floorplan maximizes both functionality and comfort, creating an ideal environment for daily living and entertaining. The open-concept design enhances the flow between spaces while maintaining distinct areas for various activities. As a new construction home, this residence provides the peace of mind that comes with updated systems, energy-efficient features, and builder warranties. The quality of design is evident in the attention to detail and careful planning that went into creating this comfortable living environment.

5192 Center Lake Ranch Boulevard, St Cloud
$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! This vibrant community offers endless opportunities to stay active, relax, and connect. Unwind by the resort-style pool, sip a drink at the Bahama Bar, or lounge in a private poolside cabana. Stay energized with tennis, pickleball, and bocce ball courts, or enjoy a workout at the state-of-the-art fitness center. Indulge in signature spa services, gather around the firepit with friends, or let your pup play at the bark park. Every day brings new possibilities in this thoughtfully designed community where you can live life to the fullest! Located near the sought-after Bridge-Prep 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. Experience resort-style living at Esplanade at Westview in Kissimmee! This vibrant community offers endless opportunities to stay active, relax, and connect. Unwind by the resort-style pool, sip a drink at the Bahama Bar, or lounge in a private poolside cabana. Stay energized with tennis, pickleball, and bocce ball courts, or enjoy a workout at the state-of-the-art fitness center. Indulge in signature spa services, gather around the firepit with friends, or let your pup play at the bark park. Every day brings new possibilities in this thoughtfully designed community where you can live life to the fullest! Located near the sought-after Bridge-Prep Academy of Osceola charter school. MLS#

4364 Curacao Place, Kissimmee
$299,000
2 Beds ⋅ 2 Baths ⋅ Birchwood Nbhds B & C SubDv. ⋅ 34773 Zip Code
Welcome home to this adorable cottage nestled in the heart of the community! Roof installed (2022). Relax and unwind on the inviting front porch before stepping inside to an open and airy floor plan designed for comfortable everyday living. This charming home features 2 bedrooms and 2 bathrooms with a desirable split-bedroom layout, offering added privacy for both owners and guests. The kitchen is equipped with beautiful 42-inch wood cabinets and overlooks the spacious living and dining areas, making it perfect for entertaining. The serene owner's suite opens to a peaceful garden, creating a private retreat to enjoy your morning coffee or evening relaxation. A private rear porch leads to the detached 2-car garage with convenient alley access, adding to the home's charm and functionality. Don't miss this wonderful opportunity to own this delightful cottage home! Ideally located near Harmony Community School, this home offers golf-cart-friendly access through a nearby tunnel to Harmony Middle and Harmony High School. Residents enjoy exceptional amenities including Buck Lake with community pontoon boats, kayaks, canoes, and a fishing pier, along with resort-style pools, dog parks, playgrounds, walking trails, a fitness center, and bike paths. Enjoy easy golf cart rides to the neighborhood coffee shop, pizza restaurant, and Mexican dining. Conveniently located near Orlando International Airport, Medical City in Lake Nona, and Florida’s East Coast beaches, Harmony offers the perfect blend of lifestyle, nature, and location. Don’t miss your opportunity to own this move-in-ready home — schedule your private showing today! Buyer to verify all room measurements.

3333 Bracken Fern Dr, St Cloud
$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
$409,990
4 Beds ⋅ 3 Baths ⋅ Villages At Harmony Ph 1b SubDv. ⋅ 34773 Zip Code
Welcome to 6724 Huntleigh Hammock Road in St. Cloud! This 4-bedroom, 2.5-bathroom Elston floor plan offers approximately 2,204 square feet of thoughtfully designed living space. Built 2021, the home features an open-concept main living area with a spacious kitchen overlooking the dining and living spaces, making the layout functional for both everyday living and entertaining. The backyard currently has fencing along three sides, offering added privacy while still providing the opportunity to complete the remaining side if desired. Upstairs, you'll find a versatile loft along with generously sized bedrooms and additional living space. The Elston floor plan itself, which is no longer offered for new construction within the community - giving buyers an opportunity to own a layout that is no longer available from the builder. Conveniently located in St. Cloud with access to community amenities, shopping, dining and major roadways. Schedule your private showing today and see everything this home includes!

6724 Huntleigh Hammock Road, Harmony
$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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