Historic Annapolis Charm with Beautiful Modern Updates. Just two blocks from the water and right in the heart of Historic Annapolis, this beautifully maintained 1850 Colonial combines classic architectural character with thoughtful modern updates. Enjoy an exceptional downtown location just moments from Main Street, charming shops, restaurants, waterfront dining, and everything that makes Annapolis so special. Inside, original hardwood floors, crown molding, built-in shelving, and two gas fireplaces reflect the home's historic character. The sellers have made extensive improvements, including a beautifully renovated kitchen in 2025 featuring navy cabinetry, new countertops, hardwood flooring, and a new dishwasher. The upstairs full bathroom was completely renovated in 2025, along with a refreshed powder room. Newly installed hardwood flooring on the upper levels was carefully selected to complement the home's original floors, creating a seamless transition between old and new. Beyond the cosmetic updates, significant improvements include a completely replaced high-velocity HVAC system and air handler (2022), a newly coated rear roof using the Acrymax roofing system (2023), all-new gutters and downspouts with gutter guards (2023), and a new washer and dryer (2024). Just off the kitchen, a private brick courtyard with a newly replaced rear fence offers a lovely outdoor space for dining, entertaining, or relaxing. Upstairs, three bedrooms feature hardwood floors and floor-to-ceiling built-in closets. Another wonderful feature for downtown living is the rear alley access, providing convenient access for bikes, paddleboards, and other outdoor gear. The home also backs directly to the new Annapolis parking garage off Duke of Gloucester Street, making parking especially convenient. With its historic details, extensive updates, private outdoor space, and walkable location just steps from the waterfront, this classic Annapolis home offers a wonderful opportunity to enjoy life in the heart of the city.