Welcome to 421 River Road. This meticulously maintained residence, cherished by a single family, showcases 5 bedrooms, 2.5 bathrooms, and a timeless design spanning 3,821 SqFt of living space on 2.8 acres and captivating winter river views. Sun-soaked interiors through abundant skylights and tile roofing create a naturally radiant ambiance. The front great room and living room's double doors seamlessly meld indoor and outdoor areas, leading to an expansive river-facing front patio. Seclusion is assured by the strategic placement of the house farther back on the property. The second-floor bedrooms extend the allure with personal roof balconies, providing elevated escapes. The primary suite features a cedar walk-in-closet adorned with an ensuite bathroom including a double vanity, a rejuvenating shower, a jetted tub, and enhanced by skylights. This property truly embodies sophistication and tranquility, inviting you to become part of its storied history. Dual attached 2-car garages accommodating 4 cars total, an expanse of land perfect for horses, and an inviting inground pool complete the offerings of this home's first ever offering to the public. The sale of this remarkable property encompasses a unique opportunity as it also includes, with its value duly reflected in the price, the ownership of the adjacent .28-acre property across the road, nestled along the serene riverfront. This combined offering enhances the total acreage featured in the listing and encompasses the comprehensive taxes, totaling $165.64, encompassing both town and village taxes, further enhancing the exceptional value of this exquisite package. Nearby are local beaches, fine restaurants, shopping district and Stony Brook University and Medical Center. Smithtown Schools.