Discover a rare gem in the heart of historic New Windsor! 312 High Street presents an exceptional opportunity to own a meticulously preserved classic residence, where timeless elegance meets modern comfort. This captivating home, rich in history and brimming with original details, invites you to experience a bygone era while enjoying the conveniences of today. Character Abounds: From intricate moldings and original wood floors to beautiful fireplaces and period-appropriate hardware, every corner tells a story. Multi-level sitting porches on both above-grade levels give intimate spaces to enjoy the quiet aesthetic of times past. Grand Proportions: Experience the luxury of spacious living with generously-sized rooms, and soaring ceiling heights throughout. With the flexibility of both a large parlor and a more cozy den area, plus a formal dining room, there are multiple opportunities for both casual and more formal entertaining. An open split staircase in the foyer adds to the grandeur of the entrance, and a traditional rear staircase off of the kitchen area provides easy access to the primary bedroom. Mature Landscaping: Step outside into a tranquil oasis, where mature trees and character plantings create a beautiful and serene at-home setting. You'll be sure to enjoy morning coffee (or garden-style happy hours with neighbors!) on the naturally scaped patio--a key part of the level fenced yard space. Historic New Windsor Charm: Nestled in the small, picturesque Historic town of New Windsor, you'll enjoy several "mom and pop" style establishments nearby for a quick bite. Scenic country roads also lead you to nearby Westminster for easy access to even more shopping and restaurants. Ready for You To Enjoy: This home has been both loved and very well cared for. Systems have been maintained, and the property shines both inside and out. Even the cellar of this special residence is extremely clean and refined, giving extra space for storage, hobbies, and more. This traditional full-brick home also delivers the practicality of both a detached carriage house (with parking for one car plus steps to ample storage space on the second level) and several dedicated parking spaces off of the alleyway. 312 High Street is more than just a home; it's a piece of history. Don't miss this exciting opportunity to own a truly exceptional property. Be ready to schedule a private showing soon, and step into a world of timeless elegance.