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

$409,990
4 Beds ⋅ 3 Baths ⋅ Villages At Harmony Ph 1b SubDv. ⋅ 34773 Zip Code
Photos coming soon! Welcome to 6724 Huntleigh Hammock Road in St. Cloud! This 4-bedroom, 2.5-bathroom Elston floor plan offers approximately 2,260 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 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
$425,900
4 Beds ⋅ 4 Baths ⋅ Pine Glen SubDv. ⋅ 34771 Zip Code
Spacious Corner-Lot Home with Dual Primary Suites – Minutes from Lake Nona & Orlando Welcome to this impeccably maintained two-story home with the perfect blend of space, comfort, and convenience. A standout feature of this home is its two spacious primary suites, each with a private en-suite bathroom and walk-in closet.  One on the first floor and another upstairs - ideal for multigenerational living, guests, or added privacy. The open-concept floor plan creates space for entertaining. The kitchen showcases enhanced lighting, quartz countertops, a closet pantry, a large center island with breakfast bar seating, and new appliances. Situated on a corner lot with a large yard that offers plenty of room to fence in for pets, play, or your own private outdoor retreat. The home also features a two-car garage. Pine Glen has great amenities including a large park with playground and soccer fields, dog park, tennis court, basketball court, and sidewalks throughout. Additional highlights: Solar panels Ring security system with cameras Low HOA fees Excellent location with convenient access to Lake Nona, Orlando, good schools, shopping, dining, and theme parks.

6352 Sprucepine Lane, St Cloud
$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
$420,000
4 Beds ⋅ 2 Baths ⋅ Deer Run Estates Ph 2 SubDv. ⋅ 34772 Zip Code
Why wait for new construction when this home is available NOW and priced competitively, with the upgrades already completed? Welcome to this move-in ready home in the highly desirable Deer Run Estates community, offering the popular 1989 floor plan by KB Homes a thoughtfully designed one-story floorplan known for its functionality, comfort, and modern appeal. This 4-bedroom 2-bathroom home with a 2 car garage features 1989 square feet of living space and all-concrete block construction, providing durability and peace of mind. The open-concept layout is ideal for both everyday living and entertaining, with a spacious upgraded kitchen overlooking the living and dining areas and extending seamlessly to a covered lanai and a fully fenced in yard, perfect for indoor-outdoor living. The kitchen is well-appointed with upgraded stainless steel appliances, a large center island, a full water filtration system with reverse osmosis drinking water, and a pantry offering ample storage. Luxury Vinyl Plank flooring runs throughout the main living areas and wet spaces, while all guest bedrooms feature comfortable carpeting and closets, allowing flexibility for bedrooms, office space, or additional uses. The primary suite is privately located at the rear of the home and includes an en-suite bathroom with double vanity, walk-in closet, and generous space for daily routines. Three additional bedrooms share a secondary bathroom, and the home is complete with a dedicated laundry room with privacy doors and a spacious two-car garage. The existing solar system helps reduce monthly utility costs, providing energy efficiency and potential long-term savings. Conveniently located approximately 30 minutes from Lake Nona and the popular Boxi Park entertainment district, you'll have easy access to dining, shopping and medical facilities. Cocoa Beach and the Kennedy Space Center are only about an hour away, making beach days and Space Coast adventures easily accessible. Schedule your private showing today and take advantage of move-in ready new construction without the wait!

3832 Pronghorn Dr, St Cloud
$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
$529,990
4 Beds ⋅ 4 Baths ⋅ Waterlin 45'S SubDv. ⋅ 34772 Zip Code
Virtually Staged. Under Construction. The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provides ample space for everyone. Sample Image

224 Cypress Fork Trail, St Cloud
$455,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Sunbridge Ph 2a SubDv. ⋅ 34771 Zip Code
Why wait to build when this like-new waterfront Hallmark home in Del Webb Sunbridge already offers panoramic pond views, completed upgrades and an exceptional move-in-ready Florida lifestyle? Located in St. Cloud’s premier gated 55+ active-adult community, this beautifully maintained, single-story home features the highly desirable HALLMARK FLOOR PLAN—NO LONGER OFFERED FOR NEW CONSTRUCTION in Del Webb Sunbridge. Built in 2023, it offers approximately 1,650 square feet with three bedrooms, two full bathrooms and a two-car garage—giving buyers the benefits of newer construction without the wait or added expense of completing major improvements after closing. The light-filled, open-concept floor plan seamlessly connects the kitchen, dining and gathering areas for comfortable everyday living and entertaining. The kitchen features quartz countertops, stainless-steel appliances, a natural-gas cooktop, built in oven and microwaves, pull-out cabinetry and a custom pantry with built-in shelving. Tile flooring flows throughout the entire home with no carpet, while a custom credenza and tinted-glass front door add style and functionality. Privately positioned at the rear of the home, the primary suite enjoys peaceful water views, a custom-designed walk-in closet and an upgraded walk-in shower with a built-in bench. Two secondary bedrooms are thoughtfully located away from the primary suite near the second full bathroom, creating excellent privacy and flexibility for overnight guests, hobbies or a home office. The true showpiece is the OVERSIZED SCREENED LANAI with an extended paver patio and PANORAMIC WATER VIEWS. Already PRE-PLUMBED FOR A FUTURE SUMMER KITCHEN, this exceptional outdoor living space is ready for sunset cocktails, relaxed mornings and year-round entertaining. Additional upgrades include a spacious laundry room with added cabinetry, generous storage and a utility sink; a salt-free water-softening system; natural gas servicing the tankless water heater and dryer; an epoxy-coated garage floor; and an insulated garage door. DEL WEBB SUNBRIDGE IS A GATED 55+ ACTIVE-ADULT COMMUNITY centered around the 27,000-square-foot Hammock Club, offering resort-style pools, a heated spa, fitness center, pickleball and tennis courts, walking trails, dog park, Tavern & Grille, resident clubs and a full social calendar. All outdoor yard maintenance and internet service are included for a convenient, low-maintenance lifestyle. Ideally located near Lake Nona, Orlando International Airport, Brightline and routes to Port Canaveral, this is the perfect lock-and-leave home base for enjoying Florida, traveling and staying close to family.

2499 Cliff Way, St Cloud
$460,000
3 Beds ⋅ 3 Baths ⋅ Twin Lakes Ph 2a-2b SubDv. ⋅ 34772 Zip Code
Virtually Staged. Why wait to build when you can own the lowest-priced "Cocoa" floor plan in one of Central Florida's premier 55+ active adult communities! This beautifully upgraded home is move-in ready and offers BRAND NEW PLANK CERAMIC TILE and UPGRADED LIGHTING. From the moment you arrive, you'll appreciate the lush tropical landscaping, paver drive and walkway, a welcoming covered front porch, and desirable PREMIUM CORNER LOT enhanced by a decorative wrought-iron fence. An elegant entry with tray ceiling, soaring 10-foot ceilings, warm designer colors, and natural wood-look plank tile flooring create a beautiful backdrop that flows throughout the entire home. The thoughtfully designed floor plan begins with two spacious guest bedrooms and a shared full bath. As you continue, you'll find a powder room for guests, while a versatile flex room provides the perfect space for a home office, reading room, hobby area, or additional storage. The heart of the home is truly spectacular. Designed for both everyday living and entertaining, the chef's kitchen showcases 42-inch cabinetry with crown molding and hardware, an abundance of granite countertop space, stainless steel appliances, a natural gas cooktop with a stylish vent hood, built-in oven and microwave. An oversized pantry, a spacious laundry room with storage cabinets is conveniently located just off the kitchen and leads to the garage, complete with epoxy flooring. A large curved island with elegant pendant fixtures provide generous seating, making it the perfect gathering place for casual meals, conversations, and entertaining family and friends. The incredible open-concept kitchen flows effortlessly into the dining and living areas, featuring recessed lighting, and an entertainment niche creates an inviting space where everyone can stay connected. Privately tucked away, the spacious primary suite offers a beautiful tray ceiling, abundant windows that fill the room with natural light, and a peaceful atmosphere designed for relaxation. The luxurious ensuite bath feels like your own private spa, complete with an extended comfort-height granite vanity, an oversized walk-in shower featuring frameless glass, upgraded shower tile, multiple shower heads, built-in bench, shampoo niche, linen closet, private water closet, and an expansive walk-in closet. One of the home's most impressive features is the wall of pocket sliding glass doors with remote controlled blinds, that completely opens the living area to the screened, covered lanai. Finished with pavers and already plumbed for a future outdoor kitchen, this is the perfect place to unwind year-round while overlooking your peaceful backyard retreat. Living in Twin Lakes means every day feels like a vacation. This vibrant, resort-style community offers an exceptional lifestyle with outstanding amenities designed for both relaxation and recreation. Residents enjoy a stunning clubhouse with a ballroom, state-of-the-art fitness center, game room, card room, and numerous social activities. Outdoors, you'll find resort-style swimming pools, tennis, pickleball, bocce ball, basketball courts, scenic walking and biking trails, plus access to Live Oak Lake where residents can enjoy boating/kayaking. Even better is the low maintenance of having HOA maintain your lawn/landscape and exterior pest control, giving you more time to enjoy the incredible Florida lifestyle. Located near shopping, restaurants, Lake Nona Medical Center, VA hospital, and Orlando Int'l airport.

2757 Southland Street, St Cloud
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