Chickasaw Trails Homes for Sale

Welcome to Chickasaw Trails, a hidden gem nestled in the vibrant city of Orlando, Florida! This charming subdivision in Orange County offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Chickasaw Trails is characterized by its beautifully landscaped streets, friendly neighbors, and a strong sense of community. Residents enjoy access to a variety of amenities, including parks, playgrounds, and walking trails, perfect for outdoor enthusiasts seeking a leisurely stroll or an invigorating run. The subdivision is conveniently located near major highways, providing easy access to downtown Orlando, world-famous theme parks, and a plethora of dining and shopping options.

The homes for sale in Chickasaw Trails showcase a diverse range of architectural styles, from modern single-family homes to cozy townhouses. Many properties feature spacious layouts, updated kitchens, and lush backyards, ideal for entertaining or simply enjoying the Florida sunshine. Whether you’re looking for a starter home or a larger residence to accommodate your growing family, Chickasaw Trails has something for everyone.

In addition to its appealing homes, this community is served by highly-rated schools, making it an excellent choice for families with children. With a strong sense of belonging and a welcoming atmosphere, Chickasaw Trails invites you to experience the best of Orlando living. Explore the available homes for sale today and discover your dream home in this delightful subdivision!

Newest Chickasaw Trails Homes for Sale

$530,000

4 Beds ⋅ 3 Baths ⋅ Chickasaw Trails SubDv. ⋅ 32829 Zip Code

Welcome to this lovely four-bedroom, 2.5-bath home nestled in the highly sought-after Chickasaw Trails community. This residence combines comfort, style and functionality. Enter inside to the spacious formal living area, featuring cathedral ceilings and a cozy wood-burning fireplace. The primary suite is conveniently located on the first floor, providing privacy and ease of access. A separate formal dining area makes entertaining a delight, while the open layout between the kitchen and family room creates a seamless flow throughout the home. Upstairs, you'll find three additional bedrooms, perfect for family, guests or flexible use as a home office. Enjoy Florida living at its best in the beautiful lanai with a cathedral-height screened enclosure, overlooking a conservation area, the perfect setting for peace, privacy and quiet relaxation. This home is packed with updates, including a new roof (2021), solar panels (2021) and a new water heater. Additional features include updated kitchen and appliances 2025/2026, granite countertops with new cabinetry, a two-car garage, well-manicured mature landscaping and low HOA fees. All of this is conveniently located just minutes from SR 417, with shopping, dining and schools nearby.

3920 Running Water Drive, Orlando

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