414 High Street, New Windsor, MD 21776Asking Price of: $499,900

Gorgeous! Step into timeless elegance at 414 High Street, a beautifully updated Colonial in the heart of historic New Windsor! This stately 3-bedroom, 2.5-bath home brimming with character and modern comforts sits on a generous half-acre corner lot. Exciting news: This address is included in an upcoming state streetscape project, which will add brand-new sidewalks and pedestrian lighting—enhancing walkability, safety, and curb appeal for the entire neighborhood! Entering a foyer off of the long side porch, you'll find a welcoming dining room with plenty of built-ins, a wood-burning insert—perfect for gatherings—and a spacious kitchen with ample cabinetry, recessed lighting, and a handy pantry. Check out the powder room where you'll see a modern twist on an antique that was once the heartbeat of every household! The formal living room has more built-ins and a cozy gas fireplace. Notice the original oil lamp hardware in the family room and all of the beautifully refinished floors. Upstairs, the primary suite is a true retreat, featuring a brand-new private balcony off of a large walk-in closet with plenty of room for an office — ideal for working from home or unwinding in style. Vintage charm meets modern luxury in the suite’s private bath featuring a refinished clawfoot tub. More large bedrooms and a shared bath along with a dedicated laundry room complete the upper level. The basement doubles as a workshop and features an electric fireplace, making it a versatile space for hobbies or relaxation. A brick paver patio, privacy fencing, dedicated garden shed, and a rare detached three-car garage are perfect offer a rare combination of modern utility and historic charm in the heart of town. Recent upgrades include newer windows and roof, a new boiler and HVAC system, water heater, and a fully replaced public water supply line to meet county requirements—giving you peace of mind for years to come. Don’t miss your chance to own this historic gem with modern upgrades and unbeatable small-town charm!