This captivating Craftsman home with modern guest house provides the ideal setting for celebrating the Eastport lifestyle and is in the best location for exploring everything Annapolis/Eastport has to offer. The picturesque picket fence welcomes you onto the property and the front porch swing is the perfect place to unwind after a long day or have your morning coffee. The charming details from the 1920's are beautifully preserved throughout with the modern convenience of an updated kitchen, bathrooms and lighting fixtures. The open floor plan creates a wonderful entertainment space and the spectacular kitchen with large island makes hosting large or small gatherings a breeze. The full bathroom and mudroom adjacent to the expansive rear deck is conveniently located to encourage the party to spill outside and creates the ideal setting for indoor/outdoor living all year round. Upstairs enjoy 2 bedrooms with soaring ceilings, exposed beams, beautiful finishes and the luxurious bathroom featuring double sinks, curated finishes and soaking tub with shower. The quaint garage has been converted to a stunning guest house with spacious main level featuring 2 story ceilings, fireplace with built-in bench/TV entertainment area, sleek modern kitchen with enormous island and powder room. Upstairs is a loft bedroom, walk-in closet and full bath with catwalk balcony overlooking the space below. The coveted off street parking space and an abundance of street parking is a rare find. This property is the perfect location for a permanent residence, weekend getaway home or rent one or both dwellings to generate income all year long. Stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and street-end parks with hidden treasures. Not to mention you are merely steps away from downtown Annapolis and Naval Academy. Annapolis offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC.