Perfectly sited on over a quarter-acre gated lot on Second Street, this meticulously maintained Eastport estate offers 4,500+ square feet of luxurious living space and extensive oak flooring in one of Annapolis’ most coveted neighborhoods. Enjoy the tranquility of suburban-style privacy with the walkability of downtown living - just steps to water access, acclaimed restaurants, shopping, and marina life. Inside, generous proportions define the main level. A spacious living room and elegant formal dining room open to the expansive deck and pool area, while a chef’s kitchen boasts a quartzite island, high-end appliances, and a casual eat-in space. The main level also features an updated laundry room, chic powder room, and a dramatic family room with vaulted wood ceilings, gas fireplace, and sliding doors to the outdoor oasis. Upstairs, the serene primary suite features vaulted ceilings, a walk-in closet, and a spa-inspired bath with heated floors, a rainfall shower, double vanity, and heated towel rack. Three additional oversized bedrooms and a stylish hall bath complete the second floor. The third level offers breathtaking views of Historic Annapolis and the Naval Academy from the rooftop balcony - perfect for fireworks or Blue Angel flyovers - and includes a family room, kitchenette, full bath, and bedroom. The fully finished lower level is made for entertaining, with a rec room, custom bar (complete with kegerator and refrigerated drawers), a flexible bonus room ideal for a wine cellar or storage, and a workshop. Step outside to your private resort: a heated in-ground pool and spa with motorized cover, a pergola with adjustable louvers, lush landscaping, and a park-like front yard. Additional features include Hardie siding, composite decking, updated windows and gutters (all completed in 2019), a two-car garage, and a gated driveway. This is a rare Eastport offering where timeless elegance, thoughtful updates, and premier location come together. Welcome Home!