Set within the desirable Sleepy Hollow Development in Athens, NY, 286 Tommy Trail is a distinctive and tastefully updated 4-bedroom, 2-bath round home offering a unique blend of architectural character and modern comfort. Recent improvements include a brand-new roof and new ductless mini-split systems providing efficient air conditioning and year-round comfort. The second floor offers an open-concept living area filled with natural light and views of the Catskill Mountains, with two bedrooms and two full baths, creating an inviting atmosphere for everyday living and entertaining. The entry-level floor features two bedrooms and a comfortable family room—ideal for guests, extended family, an office, or flexible living space. Outdoor living is equally impressive, with a wraparound deck designed for relaxation and gatherings, along with a private deck off the primary bedroom - complete with a hot tub for year-round enjoyment. The flexible floor plan provides generous bedroom space and functional living areas, making the home well suited for full-time living, a weekend retreat, or an income-producing property. The home has a successful short-term rental history, with income details available upon request for interested buyers. Set in a peaceful residential community yet conveniently located near the Hudson River, village amenities, and major routes, this property offers both privacy and accessibility. A truly special opportunity in a sought-after neighborhood—move-in ready and ready to be enjoyed.