$517,866Average Value$231Average Price per Sq Ft2Homes For Sale
Country living a stone's throw from Disney
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
Interested in learning more about homes in this area?
Reach out to
Francine Arroyo Santowski,
an experienced agent in this neighborhood.
Parks in this Area
Charlie's Park
Picnic Area
Trails
Playground
Bridgewater Crossing Community Park And Pool
Basketball
Grills
Picnic Area
Spring Park
Picnic Area
Pool
Trails
Northeast Regional Park
Baseball/Softball
Basketball
Boating
Lake Sylvia Park
Grills
Lake
Picnic Area
East Crescent Park
Pool
Events
Multi-Purpose Field
Indian Creek Park
Transit
Airport
Orlando International
43 min drive
Crime and Safety
1 - Low Crime, 10 - High Crime
Happy Trails
US
Homicide
1
4
Sexual Assault
2
4
Assault with Weapon
2
4
Robbery
2
4
Burglary
2
4
Motor Vehicle Theft
3
4
Larceny
3
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Happy Trails Demographics and Home Trends
On average, homes in Happy Trails, Champions Gate sell after 24 days on the market compared to the national average of 70 days. The median sale price for homes in Happy Trails, Champions Gate over the last 12 months is $270,000, down 34% from the median home sale price over the previous 12 months.
Under Construction. Washer, Dryer, & Refrigerator Now Included! Own a part of the magic in Central Florida's resort-style community. 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
Under Construction. Washer, Dryer, & Refrigerator Now Included! Own a part of the magic in Central Florida's resort-style community. 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
Under Construction. Own a part of the magic in Central Florida's resort-style community. Upon entering The Laguna III, guests are greeted by a grand foyer that leads to a home built with entertaining in mind. The kitchen features an expansive island complemented with granite counter tops, a breakfast bar, a chef-worthy pantry, a breakfast nook and stainless-steel appliances. The Laguna III boasts
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...
SPACIOUS 7-BEDROOM, 5.5-BATHROOM SINGLE-FAMILY RESIDENCE BUILT IN 2018 AND OFFERING 4,051 SQ FT OF LIVING SPACE ON A 6,098 SQ FT LOT. THIS LUCRATIVE AND UPDATED VACATION RENTAL BRINGS IN $100K IN GROSS ANNUAL REVENUE. CLOSE TO ALL THEME PARKS AND ACTIVITIES, IT IS A GREAT INVESTMENT THAT AN OWNER CAN ALSO USE THEMSELVES. FEATURES INCLUDE A GARAGE CONVERTED INTO AN EXCITING NEON GAMEROOM THAT THE
Best-Priced 5-Bedroom Townhouse in Windsor at Westside!Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom two-story townhouse located in the sought-after resort community of Windsor at Westside in Kissimmee. Built in 2020, this home features a private screened-in pool and the added benefit of no rear neighbors, offering extra privacy.The main level welcomes you with a
Beautiful 3BR/2BA fully furnished condo on the second floor with golf course views. Features an open floor plan, spacious living/dining area, and a covered balcony perfect for relaxing. All bedrooms are upstairs. Located in Champions Club at ChampionsGate with access to clubhouse, pools, gym, tennis courts, and more. Just minutes from Disney and major highways — great for residence or short-term
Resort-style living in ChampionsGate! This modern and spacious two-story home, built in 2021, is located in the highly desirable ChampionsGate Resort and features 6 bedrooms, 5 bathrooms, a flexible loft space, and a screened-in private pool—perfect for relaxing or entertaining. The layout includes one guest suite downstairs, with five additional bedrooms upstairs, including two primary suites,
Champions Gate Luxury Living Awaits! Resort-Style Home for LeaseImagine living in a brand-new, spacious home nestled within the amazing Champions Gate resort community! This multi-generational gem boasts 4 bedrooms, a den, a dedicated office space, and 4 luxurious bathrooms, all on a premium lot with a serene conservation view.Inside, you'll discover an elegant kitchen featuring gleaming
Interested in learning more about homes in this area?
Reach out to
Francine Arroyo Santowski,
an experienced agent in this neighborhood.
Average Home Value
Source: Public Records
Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Total Population
5,878
Median Age
36
Population Density
2 ppl/acre
Population under 18
24.1%
On par with the national average
23.8%
Population over 65
11.4%
Below the national average
19.1%
Finances
Median Household Income
$72,515
On par with the national average
$71,702
Average Household Income
$104,873
Education and Workforce
High School Graduates
96.4%
College Graduates
42%
Above the national average
34.1%
Advanced Degrees
13.3%
% Population in Labor Force
78.1%
Above the national average
65.1%
Weather
Annual Precipitation
52''
Average Winter Low Temperature
47°F
Average Summer High Temperature
92°F
Annual Snowfall
0''
Area Factors
Somewhat Bikeable
Bike Score®
25/ 100
Car-Dependent
Walk Score®
0/ 100
Source: Walk Score
Source: Walk Score
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
