Kissimmee Homes with Horses Allowed Community Features

Kissimmee Homes with Horses Allowed Community Features

Welcome to Kissimmee, Florida—where the magic of the Sunshine State meets the charm of a vibrant community! Nestled in Osceola County, Kissimmee is a delightful city known for its rich history, picturesque landscapes, and proximity to world-renowned attractions. Just a stone’s throw away from Walt Disney World and Universal Studios, Kissimmee offers residents an unparalleled lifestyle filled with adventure and entertainment.

For those who cherish the equestrian lifestyle, Kissimmee boasts several homes within communities where horses are not just welcome but celebrated! Imagine waking up in a spacious home surrounded by lush pastures and scenic trails, perfect for riding and enjoying the great outdoors. These horse-friendly communities provide ample space for stables, riding arenas, and plenty of room for your equine companions to roam freely.

In addition to its equestrian amenities, Kissimmee is home to a variety of parks, recreational areas, and nature preserves, making it a haven for outdoor enthusiasts. The city’s warm climate allows for year-round enjoyment of activities such as hiking, fishing, and horseback riding. With a strong sense of community and family-friendly events, Kissimmee is not just a place to live, but a place to thrive.

Whether you’re drawn to the excitement of nearby attractions or the tranquility of a horse-friendly lifestyle, Kissimmee is the perfect blend of adventure and serenity. Explore the possibilities of calling this enchanting city home, where your equestrian dreams can become a reality!

Newest Kissimmee Homes with Horses Allowed Community Features

2 Beds ⋅ 2 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code

Welcome to your next investment opportunity or Florida getaway in the heart of Kissimmee! Whether you're looking for a vacation home, income-producing property, long-term rental, or primary residence, this beautifully maintained 2-bedroom, 2-bath condominium offers the flexibility and location today's buyers are searching for. Ideally situated just 20 minutes from Walt Disney World and only minutes from shopping, dining, banks, grocery stores, and major roadways, you'll enjoy the convenience of being close to everything Central Florida has to offer. Inside, you'll find a bright and inviting floor plan featuring tile flooring throughout—no carpet—making maintenance and cleaning a breeze. The condo is allowing for a seamless transition whether you're planning to move in, rent it out, or continue generating income immediately. Located within a secure gated community, residents and guests enjoy an impressive array of resort-style amenities, including two sparkling swimming pools, a fitness center, tennis courts, basketball courts, and volleyball courts. The community's attractive amenities and prime location make it highly desirable for both long-term residents and vacation travelers alike. At the same time, its versatile layout and outstanding location make it equally appealing for those looking to enjoy the Florida lifestyle themselves. Opportunities like this don't come along often. Schedule your private showing today and discover why this Kissimmee condo is the perfect blend of location, convenience, lifestyle, and investment potential.

4103 Tropical Isle Blvd Unit 123, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Happy Trails Unit 3 Unrec SubDv. ⋅ 34747 Zip Code

Peaceful living at its finest in Happy Trails, a gated community, minutes from the Disney Resort! Renovated 4/3 main house with separate 927 sf in law quarters and office/studio with 483 sf. This property is ideal for extended and multi generational families. Brand new kitchen with solid wood cabinets, butler's pantry, quartz countertops and stainless steel appliances. All 3 bathrooms remodeled in 2025 with quartz countertops, wood cabinets and high end fixtures. Brand new engineered wood flooring with wide baseboards installed throughout and interior freshly painted. Ugrades include new hot water heater 2025, Metal roof 10/21, 2 zone ac 6/21 and new window treatments throughout. Bring your horses, this property is Equestrian ready with room in barn for horse stalls or large storage area & fenced paddock. Property includes 6.2 acres. There are 2 separate adjacent lots also available for sale.

2477 Thacker Trail, Kissimmee

5 Beds ⋅ 9 Baths ⋅ Happy Trails Unit 5 SubDv. ⋅ 34747 Zip Code

Welcome to a truly unparalleled luxury estate, nestled on 5 acres of serene privacy. This custom-built masterpiece, completed in 2009, boasts an impressive 11,138 square feet of meticulously designed living space, where every detail has been thoughtfully curated for the discerning homeowner. As you enter through the private gate, you are greeted by a stunning family room featuring a handcrafted stone gas fireplace and soaring ceilings that create an inviting atmosphere. The elegant curving marble staircase, adorned with a magnificent Swarovski crystal chandelier, sets the tone for the opulence that awaits. This estate offers 5 spacious bedrooms, each with large walk-in closets and en-suite bathrooms, ensuring comfort and privacy for family and guests alike. The main living areas are enhanced by exquisite woodwork, including a gorgeous dining room and a living room that seamlessly connects to the outdoor oasis through sliding glass doors that open at the corner, perfect for entertaining. Indulge in the ultimate entertainment experience in the media room, complete with luxurious seating and a stunning chandelier commissioned from Tiffany's in New York. The primary suite is a true retreat, featuring a cozy sitting area and an expansive closet. Additional highlights include a gym with a steam room, an office/study/library, and an upstairs game room that overlooks a spacious covered balcony. The outdoor amenities are equally impressive, featuring a large pool with a spa, ample undercover seating, an outdoor kitchen, and tennis courts, all surrounded by lush landscaping and majestic oak trees. The estate also includes a wine cellar, a wet bar with custom woodwork, and coffered ceilings adorned with unique prints. With a 4-car side garage and an attention to detail that is truly one of a kind, this estate is unlike anything you have ever seen. Experience luxury living at its finest—schedule your private tour today and discover the extraordinary lifestyle that awaits you.

8590 Apache Trail, Kissimmee

Happy Trails SubDv. ⋅ 34747 Zip Code

LOCATION, LOCATION...Parcel located in the exclusive GATED community of HAPPY TRAILS. Offering seclusion and privacy, Happy Trails is in a fantastic location, just a few miles from Walt Disney World and nearby Champions Gate. This lot will require mitigation. Natural Flowing Stream on Property and Wetlands. Each Buyer must independently verify and is solely responsible for the feasibility study, environmental due diligence, and survey to determine whether the Property is suitable for Buyer's intended use. Make your appointment today!

Keefer Trail, Kissimmee

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