Step into history at the Thomas-Kirby House (c.1860), a charming renovated colonial in the heart of town with picturesque street views toward Saint Michaels Harbor. This light-filled historic residence showcases beautiful hardwood floors, two staircases, detailed millwork, and rich wood accents throughout. The welcoming foyer with its 'Seaport' hand painted mural wallpaper opens to a cozy study with fireplace and custom built-ins. The comfortable dining room flows seamlessly into the updated kitchen, appointed with a new center island, upgraded features and appliances. A double-sided fireplace serves both spaces, adding warmth and character. The light-filled living room, complete with its own fireplace and entertainment center(which conveys), opens through French doors to an extended brick patio, perfect for indoor-outdoor living. Upstairs, the stunning primary suite with its cathedral ceiling, offers large built-in wardroom space, gardens views, a private balcony, and beautiful ensuite bath featuring a clawfoot tub and glass-enclosed shower. Two additional large guest bedrooms share a full bath with a luxurious steam shower, and a conveniently located second-floor laundry room completes this level. Outside, a charming brick footpath winds behind the home, connecting to an off-street brick driveway. The private backyard with its new cedar shed provides a tranquil retreat with mature trees and lush landscaping, while benefiting from the extended view into St Mary's Square. With its historic charm, modern comforts, and extensive renovations made by the current owners, this home offers the perfect opportunity to enjoy the best of Eastern Shore living. *encapsulated crawlspace and attic; new American Standard Platinum 18 SEER System; Aprilene whole house dehumidifiers (2 units); complete restoration and painting of interior and exterior are just some of the Upgrades