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.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Happy Trails neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Happy Trails
US
Homicide
1
4
Sexual Assault
3
4
Assault with Weapon
2
4
Robbery
2
4
Burglary
3
4
Motor Vehicle Theft
3
4
Larceny
4
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Happy Trails Demographics and Home Trends
On average, homes in Happy Trails, Champions Gate sell after 119 days on the market compared to the national average of 54 days. The median sale price for homes in Happy Trails, Champions Gate over the last 12 months is $499,995, consistent with the median home sale price over the previous 12 months.
***FULL GOLF AND TENNIS MEMBERSHIP INCLUDED IN HOA!!!***Assumable 5.5% VA loan*** This extraordinary one-story New Castle model combines luxury, lifestyle, and an unbeatable setting with premium golf-course frontage on the #3 green of ChampionsGate Country Club and a south-facing saltwater pool/spa perfectly positioned for incredible views of fireworks and floating hot air balloons; showcasing
Upon entering the Malibu III, guests are greeted by a grand foyer that leads to a home built for entertaining. The kitchen features an expansive island complemented with granite counter tops, a chef-worthy walk-in pantry, a dining room, and stainless-steel appliances. At 3,500+ square feet, the Malibu III boasts 7 bedrooms, 6.5 bathrooms, a 2nd-floor loft and a gathering room bathed in natural
Turnkey investment opportunity in Champions Gate! This stunning 4-bedroom, 3-bathroom townhome is fully furnished, professionally decorated, and located in one of Central Florida’s most sought-after short-term rental communities, just minutes from Disney World and Orlando’s top attractions. The home offers a spacious open-concept layout ideal for vacationing families and groups, with the main
Welcome to your dream vacation home! This beautifully furnished 5-bedroom, 4-bathroom retreat is nestled in the Windsor at Westside resort, offering everything you need for the ultimate getaway. Designed with a spacious two-story layout and an open floor plan, this home is perfect for large families or groups of friends. The modern island kitchen features stainless steel appliances and granite
One of the most desirable short term rental community in town, it has everything for you and your guest during your stay with club houses - pool - water park - golf course and much more... the community its pretty good located and the property is fully furniture plus if you are looking as an investment then we have the amazing rental history showing a great ROI, dont hesitate to contact me ASAP...
Experience the ultimate in resort-style living with this incredible 4-bedroom, 3-bathroom townhome, perfectly located just minutes from Orlando’s most iconic theme parks. This home is thoughtfully designed to offer both comfort and luxury, making it ideal for families, vacationers, or investors. Step into an inviting open floor plan on the main level, featuring a beautifully appointed kitchen
Luxurious 7-Bed, 5.5-Bath Retreat in Windsor at Westside! Nestled on a premium lot in the coveted Windsor at Westside gated community, this fully furnished 7-bedroom, 5.5-bathroom home is perfect for vacations, primary living, or investment, just minutes from Disney. Enjoy a spacious open floor plan with owner’s suites on both floors, a gourmet kitchen featuring stainless steel appliances,
Discover this stunning 9-bedroom, 6-bathroom vacation retreat in the vibrant Solara Resort community, just 8 miles from Disney World! Perfect for families or investors, this high-end property features themed bedrooms, elegant suites, and a spacious game room that guarantees entertainment for all ages. Step outside to your private screened-in pool and spa, complete with a covered lanai for
PRICED TO SELL!! FULLY FURNISHED TURNKEY INVESTMENT OPPORTUNITY in the highly sought-after ChampionsGate Resort, with no rear neighbors for added privacy! Perfectly zoned for short-term rentals, this stunning 4-bedroom, 3-bathroom townhome is a gem. The property boasts a private heated pool within an enclosed lanai, making it ideal for year-round enjoyment. The open-concept first floor features a
Do you enjoy spending so much time in Orlando that you think it may make more sense to own a second home here? Wouldn't you like to save money on hotels, transportation and meals; and have the ultimate freedom to visit Orlando? Why not offset the entire cost of owning a home in Orlando by investing in a lucrative home like 8913 Coconut Grove, and one that will generate income while you're not
Modern luxury design meets community convenience with this one-of-a-kind FULLY FURNISHED 3-bedroom & uniquely 3 en-suite Bathroom townhome located in the Windsor Palms community in Kissimmee! Step inside to the open-concept kitchen & living room with luxury vinyl wood flooring which continues throughout the majority of the home. Fully updated in 2024, the kitchen is one to be desired with ALL NEW
Welcome to this stunning 8-bedroom, 6-bathroom vacation home located in the highly desirable resort community of Windsor at Westside. Built in 2019, this turn-key property features the same spacious floor plan as the most sought-after models in the community and comes fully furnished and professionally decorated to maximize short-term rental income. This home offers enhanced privacy with a
One or more photo(s) has been virtually staged. Location, lifestyle and low maintenance on this newly built townhome, so why wait on construction when you can live where others vacation? Perfectly positioned in the heart of ChampionsGate, this like-new 3-bedroom, 2.5-bath home with a 2-car garage delivers the ultimate blend of convenience, comfort, and resort living. The open-concept main level
Discover exceptional resort-style living in this beautifully appointed vacation townhome, ideally located just minutes from Walt Disney World in Phase 2 of the highly regarded Solara Resort. Offering nearly 2,300 square feet of thoughtfully designed living space, this open-concept residence showcases a stylish kitchen with granite countertops and stainless steel appliances, perfect for
BEST PRICED Fully FURNISHED POOL HOME in the beautiful, amenity-packed ChampionsGate Resort! This luxurious 8-bedroom, 5-bathroom home offers privacy with no rear neighbors and is beautifully designed for both relaxation and entertainment. Featuring high-end furnishings and multiple themed bedrooms, this property promises an unforgettable experience—perfect for family getaways or lucrative
Currently offering 8 weeks free! Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market accrued is not specific to current plan listed. At Abrazo at Four Corners, home feels a little more like, well, home. Enjoy the comfort of thoughtfully designed detached and paired residences—complete with stylish interiors, spacious layouts, and private
Currently offering 8 weeks free! Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market accrued is not specific to current plan listed. At Abrazo at Four Corners, home feels a little more like, well, home. Enjoy the comfort of thoughtfully designed detached and paired residences—complete with stylish interiors, spacious layouts, and private
Currently offering 8 weeks free! Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market accrued is not specific to current plan listed. At Abrazo at Four Corners, home feels a little more like, well, home. Enjoy the comfort of thoughtfully designed detached and paired residences—complete with stylish interiors, spacious layouts, and private
Take the opportunity to live in one of the best vacation community in town, make your life part of this resort style, this property is fully furnished and decorated where you are going to feel very confortable enjoying a quiet environment with amazing community amenities.
Discover comfortable and convenient living in this well-appointed 3-bedroom, 2.5-bathroom townhome. The home features granite countertops, stainless steel appliances, and a functional open-concept layout designed for modern living.Ideally located with easy access to US-27, I-4, and Hwy 429, the property provides convenient connectivity to Orlando’s major employment centers, shopping, dining,
Discover resort-style living at its finest in this beautifully appointed 2-bedroom, 2-bathroom end-unit villa located in the highly sought-after ChampionsGate Country Club. This exceptional home includes a FULL GOLF MEMBERSHIP in the HOA! ChampionsGate Country Club offers unparalleled access to world-class amenities and championship fairways. This beautiful home is ideally situated across from
This home at 2344 Brook Marsh offers a comfortable and functional layout with 3 bedrooms and 2.5 bathrooms. It’s designed for easy everyday living, with plenty of space to relax, gather, and make yourself at home. Simple, practical, and inviting, it’s a great place to settle in and enjoy.
Step into comfort, space, and style with this turnkey, fully furnished 5-bedroom, 4-bath home, featuring two spacious primary suites—perfect for multi-generational living, extended stays, or simply enjoying extra space. From the moment you enter, you’ll notice how beautifully maintained this home is, with vaulted ceilings, an open-concept layout, and a thoughtful split-bedroom design that offers
Abrazo at Four Corners is a thoughtfully designed rental community where style, comfort, and connection come together. Our spacious one-, two-, and three-bedroom homes feature contemporary finishes and smart layouts to fit your lifestyle. Enjoy a curated selection of amenities, including a resort-style pool, modern fitness center, and inviting resident spaces built for gathering or relaxing.
Step into resort-style living in Champions Gate! This fully furnished 5-bedroom, 5-bath home is the perfect luxury rental spacious, stylish, and ready for you to enjoy from day one. The modern kitchen shines with quartz countertops and plenty of room to cook and gather, while the open living areas create the ideal setting for relaxing or entertaining. Outside, your private escape awaits: a
The advertised rate of $3,789/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
Beautiful 2024 built townhome located in the highly desirable Champions Gate area of Davenport. This modern residence offers 3 bedrooms, 2.5 bathrooms, and approximately 1,787 square feet of heated living space with over 2,100 total square feet under roof. The open concept floor plan features a spacious kitchen with contemporary cabinetry, stone countertops, and a large island overlooking the
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