Homes for Sale

If your idea of heaven is to own a house on several acres of land, Happy Trails in Kissimmee is the community for you. This secluded, private neighborhood of estate homes is the last equestrian estate in Central Florida, so you’ll find extensive trails throughout, along with lush native landscaping. You’ll feel like you’re living out in the country, but you’re only a short drive from the restaurants and shops in ChampionsGate, and Disney World is only 20 minutes away.

Check out the available Happy Trails real estate listings below! Want to learn more? Continue reading for more information, or contact us online to reach a Happy Trails home specialist!

Search Happy Trails Real Estate Listings


8525 Patricia Trl, Kissimmee

This turnkey Magnificent home sits on over 5 acres of peaceful, serene, natural beauty. Custom built in 2017 this house boasts three master …more

800 S Goodman Rd, Kissimmee

LOCATION! LOCATION! LOCATION! LOOK NO FURTHER…. THIS IS A MUST SEE!!! Amazing 3 bed/ 2 bath Single Family Home sitting on 5 acres with NO …more

Happy Trails Amenities

Like the name suggests, Happy Trails is an ideal community for horse lovers. You’ll find plenty of trails, bordered by ancient oak trees and other native fauna, that can be enjoyed on horseback in your leisure time. This untouched, natural area is not so far out in the country that you can’t enjoy the conveniences of modern life. Located near SR 429 and I-4, Happy Trails is just a few minutes from the Omni Orlando Resort at ChampionsGate, which features two 18-hole championship courses designed by renowned golfer Greg Norman, a hotel, shops and world-class dining. You can stock up on groceries at two Publix supermarkets located nearby. And you’re close enough to all the fun, thrills and excitement found at the area theme parks like Disney, Universal and SeaWorld.

Happy Trails Floor Plans

One of the things that distinguishes Happy Trails from other communities in Kissimmee is the fact that it features larger, custom built homes on several acre lots. You’ll find the majority of homes feature four, five or six bedrooms offering anywhere from 2,000 square feet to 11,000 square feet of living space. There are also empty lots still available for sale in Happy Trails, so you can build your own dream home.

If you have any questions, please don’t hesitate to call a Team Donovan real estate agent at 407.705.2616, or contact us online. We look forward to helping you find the perfect Happy Trails home for sale!