Kissimmee/Celebration Homes with Trail(s) Amenities

Kissimmee/Celebration Homes with Trail(s) Amenities

Welcome to the enchanting region of Kissimmee and Celebration, Florida, where the allure of sunshine, vibrant communities, and a touch of magic come together to create an idyllic living experience. Nestled in Osceola County, Kissimmee is renowned for its proximity to world-famous attractions like Walt Disney World, Universal Studios, and an array of outdoor adventures. Meanwhile, the charming town of Celebration, originally developed by Disney, offers picturesque streets lined with quaint shops, delightful eateries, and beautifully manicured parks.

For those seeking a home that harmonizes with nature, the Kissimmee and Celebration area boasts a variety of residences featuring exceptional trail amenities. Imagine stepping outside your front door and onto scenic walking and biking paths that wind through lush landscapes, serene lakes, and vibrant neighborhoods. These trails not only promote an active lifestyle but also foster a sense of community, with residents often seen jogging, cycling, or leisurely strolling with family and friends.

Homes in this region with trail amenities provide the perfect backdrop for outdoor enthusiasts and families alike. Whether you're enjoying a peaceful morning walk, a weekend bike ride, or an evening stroll under the stars, these trails enhance your living experience. With a plethora of parks and recreational facilities nearby, residents can indulge in a multitude of activities, from picnicking to birdwatching.

Embrace the charm and convenience of Kissimmee and Celebration, where your dream home awaits amidst a thriving community and beautiful nature trails. Discover a lifestyle that balances adventure and tranquility in this captivating corner of Florida!

Newest Kissimmee/Celebration 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
$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
$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
$84,000
Reunion Ph 2 Prcl 3 SubDv. ⋅ 34747 Zip Code
Take advantage of this unique lot to build a one-of-a-kind residence at **1523 Fairview Circle**, a beautiful water-view homesite located in the desirable Patriots Landing neighborhood of Reunion Resort. Positioned directly across from the community lake and fountain, this lot offers a peaceful setting and an attractive backdrop for the custom home you have always envisioned. Imagine enjoying morning views of the water, relaxing evenings on your future lanai, and colorful Florida sunsets from a home designed around your lifestyle. Whether your plans include a primary residence, vacation getaway, or luxury investment property, this homesite offers an exceptional opportunity to build within one of Central Florida’s most recognized resort communities. The sellers have already explored several exciting design and construction possibilities for the property and will make the information they have gathered available to the new owner, providing a helpful starting point when planning the future residence. Patriots Landing is known for its distinctive coastal-inspired architecture, mature landscaping, and welcoming neighborhood atmosphere. Reunion Resort offers an impressive lifestyle with three signature golf courses, resort-style pools, a water park, onsite dining, recreational activities, and rooftop views of the surrounding attractions and nightly theme-park fireworks. Conveniently located near Walt Disney World, major theme parks, shopping, dining, and Central Florida’s primary roadways, this homesite combines tranquility, resort living, and accessibility. Opportunities to purchase a premium water-view lot in Patriots Landing are limited. Secure this special homesite and begin creating a custom property designed to reflect your vision, goals, and lifestyle.

1523 Fairview Circle, Kissimmee
$475,000
3 Beds ⋅ 2 Baths ⋅ Terraces E Village Condo P3 SubDv. ⋅ 34747 Zip Code
Beautiful and rarely available 3-bedroom, 2-bath first-floor condo in Celebration’s East Village with desirable east exposure and a bright, open layout. This fully updated home features stainless steel appliances, quartz kitchen countertops, marble bath surfaces, ceramic tile flooring throughout, and plantation shutters. Freshly Painted. New Washer/Dryer. The spacious primary suite offers a tray ceiling, walk-in closet, and ensuite bath. Enjoy a private wraparound patio with peaceful, open views. The unit faces Blue Sage St. and is just a short walk to the East Village pool, with easy access to downtown Celebration, Disney, major highways, and Orlando attractions. Includes a detached 1-car garage.

855 Blue Sage Street Unit 102, Celebration
$210,000
3 Beds ⋅ 3 Baths ⋅ Emerald Island Resort Ph 2 SubDv. ⋅ 34747 Zip Code
This three-bedroom, two-and-a-half-bath townhouse sits within Emerald Island Resort, a guard-gated community, offering 24-hour security, resort-style amenities, and ideal accessibility to shopping, dining, and entertainment. Tile flooring throughout the main living area provides durability and low-maintenance surfaces. The outdoor living space is built into the home's design with a primary suite balcony providing a private retreat and a covered lanai extending the living area, offering a flexible space for relaxation or entertaining. The secure community setting delivers peace of mind with controlled access and 24-hour monitoring along with plenty of recreation activities including a clubhouse, fitness center, sauna, cybercafé, multiple pools, tiki bar, playground, mini golf, 11 miles of nature trails, and tennis/pickleball, basketball, and beach volleyball courts. The location delivers genuine convenience to major attractions and daily destinations. Island H2O Water Park is close by, while Disney's Animal Kingdom and Celebration Golf Club sit just minutes away. Sunset Walk Shopping and Formosa Gardens Village offer retail access nearby, with proximity to Disney, Target, Publix, Walmart, Aldi, and numerous dining and shopping centers rounding out this bustling area. Whether you want to explore Central Florida or Tampa, convenient access to SR-429 and I-4 ensure daily adventures are a breeze. This townhouse positions you near both entertainment and practical services, making daily life and weekend activities effortless. The property presents opportunity for buyers ready to personalize and update. Schedule your private showing today to explore this property and all that this area has to offer.

8407 Blue Lagoon Drive, Kissimmee
$380,000
3 Beds ⋅ 3 Baths ⋅ Heritage Crossing Condo Ph 17 SubDv. ⋅ 34747 Zip Code
Welcome to 7636 Heritage Crossing Way, where you are not simply purchasing a vacation home, but investing in one of the highest producing townhomes in Reunion Resort. Meticulously maintained and operating at an exceptional level, this property has become a true revenue generating machine while remaining in pristine condition. Unlike many short term rentals, this home shows virtually no signs of wear, with immaculate flooring, furnishings, décor, and finishes that make it feel more like a luxury second home than an investment property. One of the property's greatest advantages is that it is completely self managed. All future bookings are transferable to the new owner, and the seller is offering, though not requiring, the opportunity for the buyer to become a co host. This allows immediate access to the seller's established Superhost status and the same booking platforms and systems that have consistently produced strong rental performance. Perfectly positioned within the main Reunion community, this corner location offers the best of both worlds. It is one of the closest townhomes to the HOA maintained resort pools while also being just a short walk to nearby shopping, restaurants, and everyday conveniences. As a townhome owner, you will enjoy reduced maintenance living, with the HOA handling exterior upkeep, landscaping, and major structural elements. At the same time, this property offers a rare feature, a private backyard garden oasis that is owned by you yet maintained by the HOA, allowing you to enjoy outdoor space without the burden of upkeep. For buyers wanting to experience the renowned Reunion lifestyle without the price tag of a multimillion dollar estate, this represents one of the best values in the community. The thoughtfully designed floor plan offers three spacious primary suites, including one conveniently located on the first floor. The entire first level is wheelchair accessible, allowing the home to accommodate a wider variety of owners and guests while increasing its rental appeal. The interior has received extensive updates throughout. Furnishings were replaced between 2021 and 2025, creating a fresh and welcoming atmosphere. One of the home's most memorable features is the antique piano displayed in the living room, creating a unique first impression that guests consistently love. Additional improvements include interior and exterior paint completed in 2025, a 2022 HVAC system, wood flooring installed throughout the home in 2021 with no carpet, a full size stacked washer and dryer installed in 2022, updated toilets and plumbing fixtures completed in 2024, and a brand new roof installed by the HOA in 2025. Reunion is widely recognized as one of Central Florida's premier luxury golf resort communities, offering championship golf courses, pickleball and tennis courts, an exciting water park, multiple restaurants, scenic walking areas, and 24 hour gated and roaming security. The location is equally impressive, just minutes from ChampionsGate, Walt Disney World, shopping, dining, major highways, Orlando attractions, and convenient access to Florida's beaches. Ownership flexibility is another advantage, as the community allows short term vacation rentals, long term rentals, or full time owner occupancy. Whether you are searching for a high performing investment, a vacation retreat, or a permanent residence, this home delivers an exceptional combination of proven income, outstanding condition, and resort style living.

7636 Heritage Crossing Way, Reunion
$375,000
3 Beds ⋅ 2 Baths ⋅ Terraces At Reunion Condo Ph 20 SubDv. ⋅ 34747 Zip Code
Pristine Oasis in Reunion Resort – Golf Course Views & World-Class Amenities!** Welcome to paradise at The Terraces at Reunion! This spectacular, 2nd-floor condo perfectly blends charm, abundant natural light, and impeccable style, meticulously maintained exclusively for personal use by its current owners, this turnkey property is in pristine condition. Whether you are looking for a high-yielding short-term rental investment or a gorgeous luxury condo to call home, this property delivers on every level. **The Interior:** Step inside to an airy, open-concept floor plan designed for seamless living and entertaining. The spacious living room features two sets of elegant French doors, modern chandeliers, flooding the space with floor-to-ceiling natural light while framing the serene golf course views and multimillion dollar mansions and beyond. This corner unit elevate this residence, including: **Furnishings:** Styled with designer furniture that is negotiable with the home. The expansive master suite serves as a private retreat, complete with a generous bedroom, a large walk-in closet. For ultimate convenience, this unit includes the LARGEST private garage that fits storage plus a car and a second car outside of your garage. **The Outdoor Space:** Enjoy your morning coffee or evening sunsets from the spacious wrap-around balcony—a rare feature that makes this one the ONLY one with the BEST views of all the condos in the entire neighborhood. If you want to cool off, you are just a few steps away from the stunning community pool and park area. **The Lifestyle & Location:** Situated at **7474 Excitement Dr**, this property places you in the heart of Reunion Resort—a world-class vacation capital. Living here gives you access to an unparalleled lineup of luxury amenities: * **Water & Recreation:** 6 sparkling community pools, 6 up-scale Restaurants * **Golf:** Home to 3 of the world's most famous signature golf courses designed by legends Palmer, Watson, and Nicklaus. * **Dining & Wellness:** 6 on-site restaurants, a fully equipped fitness center, a luxury day spa, and miles of scenic walking trails. NOTE: "This is the ONLY building in all reunion with the lowest HOA option that includes still 6 pools and 6 restaurant/bars. **Proximity:** * **Theme Parks:** Minutes away from Walt Disney World and Orlando’s premier attractions. * **Travel:** Just 30 minutes to Orlando International Airport (MCO). * **Convenience:** Surrounded by a wealth of local shopping and fine dining, with easy access to both Florida coasts for effortless beach day trips. Don't miss this rare opportunity to own a piece of Orlando's premier resort lifestyle. Schedule your showing today to appreciate just how truly lovely this condo is! Discounted rate options and no lender fee future refinancing may be available for qualified buyers of this home.

7474 Excitement Dr Unit 203, Reunion
$1,049,000
4 Beds ⋅ 3 Baths ⋅ Celebration Island Village SubDv. ⋅ 34747 Zip Code
Price Just Reduced!! 30k under price! This is an Iconic Property in Island Village at Celebration, FL. Located in Phase One (the closest area to downtown Island Village and Celebration Downtown. This spectacular HILTON HEAD MODEL by Mattamy Homes was carefully UPGRADED and and sits on one of the community’s PREMIUM-WATERFRONT home sites. This amazing property offers approximately 2,800 square feet of beautifully designed living space, nearly 4,100 total square feet, 4 Bedrooms, one Flex Room, 2.5 Bathrooms, and an impressive collection of luxury builder and owner upgrades. From the moment you arrive, you’ll appreciate the oversized premium lot, breathtaking water views, and outstanding curb appeal. Inside, the thoughtfully designed open floor plan is filled with natural light and showcases wide-plank wood flooring throughout with no carpet, soaring 8-foot interior doors, a tray ceiling in the owner’s suite, elegant iron stair balusters, upgraded baseboards, custom window treatments, and designer finishes throughout. The gourmet chef’s kitchen is the heart of the home, featuring premium cabinetry with crown molding, quartz countertops, a farmhouse sink, built-in refrigerator enclosure, double ovens, designer gold hardware, upgraded lighting, and an expansive island that seamlessly connects to the spacious great room, perfect for entertaining. The first floor Flex Room with French doors provides the ideal home office, study, or playroom. Upstairs, the luxurious owner’s suite offers a spa-inspired bath with upgraded cabinetry, matte elegant fixtures, an upgraded shower enclosure, and generous closet space. Designed for today’s lifestyle, this home also includes an Oversized 2 -car garage, epoxy flooring and additional storage, an electric vehicle charging outlet, sound insulation between interior walls, pre-plumbing for a future outdoor kitchen, media wiring , additional electrical upgrades, seamless gutters, and countless thoughtful enhancements selected during construction. Step outside to enjoy tranquil water views and the privacy of one of Celebration’s most desirable homesites. Whether you’re enjoying your morning coffee or entertaining family and friends, the outdoor living space provides the perfect Florida lifestyle. Located in the award-winning community of Celebration, residents enjoy resort-style amenities, scenic walking and biking trails, community pools, parks, playgrounds, fitness facilities, and convenient access to Disney, major highways, shopping, dining, and Orlando’s world-class attractions. This is more than a home, “it’s one of Island Village’s finest opportunities”. Luxury, location, and lifestyle come together in this truly remarkable residence. Call today to schedule a private tour.

7565 Estuary Lake Loop, Celebration
$979,000
4 Beds ⋅ 4 Baths ⋅ Spring Park Townhomes SubDv. ⋅ 34747 Zip Code
Welcome to the heart of Celebration, Florida! This stunning, fully remodeled 3-story townhome offers the ultimate blend of modern luxury and convenience, located just steps from vibrant community pools, parks, trails & Downtown. The main level boasts a spacious, open floor plan with a chef’s kitchen featuring a breakfast nook, additional seating, and seamless flow into a bright living area. Upstairs, the second floor hosts two secondary bedrooms and a luxurious master suite, complete with a modern en-suite bath, & custom walk-in closet. The massive, 800 sq. ft. third-floor offers a multi-generational suite has endless flexibility and features its own living room, wet bar, and private bedroom and bathroom as well as a custom closet. Outside, enjoy a charming private patio and a 2-car garage with WiFi-enabled doors and a fully decked attic for ample storage. In addition to the modern remodel on the townhome you will also find, upgraded windows have been installed, newer AC units installed, and a energy-efficient hybrid water heater. This turnkey home is a dream come true!

1206 Celebration Avenue, Celebration
$345,000
2 Beds ⋅ 2 Baths ⋅ Siena At Celebration Condo B SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully renovated 2-bedroom, 2-bath condominium with a versatile loft, ideally located in the heart of Celebration, Florida. Overlooking the golf course, this light-filled residence offers an open-concept floor plan designed for comfortable everyday living and effortless entertaining. The updated kitchen features stone countertops, a decorative tile backsplash, abundant cabinetry, and a complete appliance package, seamlessly connecting to the spacious living and dining areas. Expansive windows fill the home with natural light while showcasing tranquil golf course views. The flexible loft provides valuable additional living space and can easily serve as a home office, media room, guest retreat, or potential third sleeping area, adapting to your lifestyle needs. Additional improvements include a new HVAC system, providing comfort and peace of mind. Located just moments from Celebration's picturesque downtown, residents enjoy an exceptional lifestyle with access to community pools, parks, playgrounds, scenic walking and biking trails, tennis and basketball courts, and year-round community events. Enjoy boutique shopping, restaurants, cafés, and waterfront paths just minutes from your doorstep. Conveniently situated near Walt Disney World®, Universal Orlando Resort™, SeaWorld®, Orlando International Airport, and major highways, this home is ideal as a primary residence, second home, or investment opportunity. Experience the perfect combination of updated interiors, flexible living space, scenic golf course views, and the unparalleled lifestyle that makes Celebration one of Central Florida's most sought-after communities.

714 Siena Palm Drive Unit 201, Celebration
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