Kissimmee’s Happy Trails is a rural enclave offering the feel of secluded, country living while being a stone’s throw from big-city life. Residents in this private community enjoy upscale ranches and estates on some of the largest wooded lots in the area. Happy Trails is one of six rural enclaves in Osceola County, and as the name suggests, opportunities to explore the great outdoors abound here. “This area is just so unique; there’s nothing else like it. It’s close to everything, but you’re in the middle of nowhere,” says Nicholas Stone, Happy Trails Property Association board member and five-year resident. Stone says after looking for a year and trying to get into the high-demand community, he, his wife and children moved from Clermont, Florida to escape the typical suburbia. “We came here for the tranquility,” he says. “We lived in a cookie-cutter community, and you had no space; you could hear everything going on. Here, you have privacy and the beauty of nature around you.” Happy Trails’ proximity to major thoroughfares allows residents to reach Walt Disney World Resort in 7 miles, and many other Central Florida attractions are under 10 miles away. “You can get to the I-4 in 4 minutes; Disney is 15 minutes away. You can be so many places so quickly.”
Centuries-old oak trees and lush native landscaping is all part of the charm of Happy Trails.
Happy Trails has estates on some of the largest wooded lots in the area.
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Custom-built ranches and million-dollar estates on 10 acres
The gated Happy Trails neighborhood offers traditional Craftsman-style homes, custom-built modern mansions, million-dollar estates and ranches. “No two homes are the same,” Stone says. “We have everything from a couple thousand square feet to one being built now that’s 18,000 square feet.” The 1,900-acre community is home to approximately 150 houses and vacant lots for those who want to build their dream home. And it’s steadily expanding. “They don’t last long on the market, and we’re growing quickly,” Stone says. “There is quite a bit of new construction for single-family homes. We have five or six that are being built now.” James Donovan, President/Broker for Team Donovan, who’s been selling in the area for over 20 years, echoes Stone’s sentiments on the appeal of Happy Trails. “It’s a huge parcel of land, so it’s like being in the countryside in another state, but it’s close to Disney,” he says. “Having no HOA is another big draw for many people. “They look here because they want to play by their own rules. You don’t have restrictions here; you can build a custom house or a warehouse and not pay any dues.” Most single-family homes were built in the late 2010s and range from approximately $270,000 for a three-bedroom around 1,400 square feet to over $1 million for an eight-bedroom home over 4,000 square feet on multiple acres or lakefront property. “Post-COVID, it picked up here; people wanted more land,” Donovan says. “Most lots are anywhere from 10 or 20 acres.”
Stone says lots must be at least 5 acres, and while many people might see that as a hassle, Happy Trails residents welcome it. “We have neighbors you can see in the distance, but they're not right on your doorstep,” he says. The property owners' association has no control over your property, so many people have horses, some have cows and sheep. You can have your animals, a boat or an RV here.” Lawns are well landscaped with winding stone walkways, and driveways are large enough for boats or RVs. Residents enjoy covered porches and pools with lanais. Many properties come outfitted with all the bells and whistles for horse enthusiasts, including barns, stalls and fenced paddocks. A canopy of towering mature oaks blankets the neighborhood, allowing for ultimate privacy and tranquility.
Windsor at Westside is one of the most popular resort style communities in Happy Trails.
Contemporary ranch homes in Happy Trails offer a budget friendly option for homeowners.
Spacious townhouses at Windsor at Westside offer great amenities in Happy Trails.
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Close to Northeast Regional Park and Hilochee Wildlife Area
While there aren’t carved-out trails in the community, Stone says residents stay active. “A lot of people go around on bikes or golf carts. People walk in the morning, too, before it gets too hot.” Northeast Regional Park is 3 miles north of Happy Trails. The complex offers multiple baseball, soccer, football and lacrosse fields. The grounds also include a nature-inspired playground, tennis courts, a boat launch and a fishing pier. Pet owners can let their dogs play in the dog park or walk along its trails. Old Lake Davenport is next door to Northeast Regional Park, a hot spot for fishing, kayaking and jet skiing. Happy Trails is close to three golf courses. The 36-hole private Champions Gate Country Club is south of Happy Trails, which offers three golf courses and seven tennis courts. The 18-hole public Highlands Reserve Golf Club is to the west and was ranked among the Top 25 Most Improved Golf Courses in the country by GolfPass in 2024. Hilochee Wildlife Management Area is 8 miles north for those who want a deeper trek into nature. The refuge offers biking, hiking, fishing and horseback riding.
Practice your penalty kicks at Northeast Regional Park.
Residents can enjoy a game of golf at nearby golf courses in Happy Trails.
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A few miles from Margarita Boulevard
The closest shopping and dining options are along Highway 27, a few miles west of the community. Anchored by Publix, Berry Town Center is also home to Sunday’s Grill, a popular UK-inspired pub known for its fish and chips, English breakfasts and live music. One mile north, residents can enjoy sushi and bento boxes at Kumo Japanese Restaurant, burgers and hand-cut fries at the no-frills Adler’s restaurant and mofongo and other traditional Puerto Rican dishes at Buen Café Latin Food. Rolling Oaks Commons Plaza is a 7-mile drive, which offers more retail options and big-box stores. A wider variety of boutiques, fine dining and nightlife await 7 miles north at the Promenade at Sunset Walk. “There is a lot to do on Margarita Boulevard,” says Stone of the shopping complex’s main street. “We like Rock & Brews.”
Happy Trails local Publix is located in Berry Town Center Shopping Plaza.
Happy Trails shoppers don't have far to go with the Promenade at Sunset Walk close by.
Happy Trails residents can take an afternoon stroll and do some shopping at Sunset Walk.
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Home to the fifth-best high school in the county
Osceola School District serves the area, and students attend Westside K-8 School in the neighboring Four Corners community, finishing their education at Celebration High School in the Celebration neighborhood. Westside, which earned a C on Niche, provides high school-level courses in foreign language, geometry, and biology for middle schoolers. Earning an A-minus on Niche, Celebration High is ranked the fifth-best public high school in the county and offers tennis and swimming teams.
Mia Pizza in Happy Trail serves classic pies, paninis and calzones with fresh ingredients.
Grab a nutritious smoothie or bowl at Acai Express & Creamery in Happy Trails.
Celebration High School provides quality education for students in Happy Trails.
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A 'happy' community
Happy Trails Property Owners Association doesn’t host specific events for the community, but Stone says the tight-knit neighborhood comes together on its own with celebrations. “It’s a family-oriented neighborhood. That’s what we enjoy, and that’s what keeps us here,” says Stone. “My wife and I have a Christmas party and invite the neighbors, and we had 30 people last year. People can put names to houses.” It’s also a community that comes together in bad times. “Some trees came down last night, knocking out the power,” Stone says. “Neighbors were out there clearing the road. Everybody helps each other.”
Happy Trails has large estate homes with plenty of acreage.
Happy Trails is known for multi-acre lots and equestrian homes.
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Seven miles from Walt Disney World Resort
Happy Trails is conveniently located a few miles from U.S. Highway 27, and Route 429 borders its eastern edge, connecting to Interstate 4, making getting around the area a breeze. Downtown Kissimmee is 22 miles away, Walt Disney World is 7 miles away, and Orlando International Airport is 28 miles away. The nearest hospital is Orlando Health Emergency Room and Medical Pavilion—Four Corners, 5 miles north. Residents will need a car as there is no public transit.
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On average, homes in Happy Trails, Champions Gate sell after 116 days on the market compared to the national average of 52 days. The median sale price for homes in Happy Trails, Champions Gate over the last 12 months is $510,000, up 6% from the median home sale price over the previous 12 months.
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