Welcome to 19 Winchester Road: an expansive 6 bedroom, 3.5-bathroom character-filled residence set on one of Lakewood Village’s most desirable, tree-lined streets. Just moments from Chautauqua Lake and near the Chautauqua Lake Yacht Club, this home offers over 4,600 square feet of living space over three levels, effortlessly blending classic architecture with thoughtful modern upgrades. Inside, high ceilings and generously scaled rooms create a sense of openness and flow, ideal for both everyday living and entertaining. The layout offers both flexibility and privacy across multiple living and gathering spaces. The home is fully equipped for modern living and peace of mind with a Brilliant Smart Home System which can control lighting, audio, temperature, cameras, smart locks, and more. In addition, the smart system includes five Ring cameras, three smart locks, Philips Hue lighting system in select rooms, Wi-Fi enabled Samsung Smart Appliances, and a Tesla Charger. Comfort and efficiency are supported by three HVAC systems with updated mechanicals (2020), three Ecobee smart thermostats, a Moen Smart Water Monitor with water leak detection and shutoff capability, and an Aquasana OptimH2O Whole Home 5-Stage Water Filtration System.  Set behind mature hedges, the property offers a rare sense of privacy within the Village. The expansive rear TREX deck creates an ideal outdoor extension of the home. 19 Winchester is part of the Winchester Dock Association, which provides access to Chautauqua Lake for just $85 per year, with space for storing kayaks, swimming, fishing, and convenient lakeside pickup and drop-off, is dog-friendly, and has no waitlist to join!  A furniture package is available, offering a seamless, move-in-ready opportunity. A rare combination of scale, privacy, and walkable Lakewood Village living, 19 Winchester is where your next chapter begins.