A rare opportunity to own a beautifully reimagined century-old residence in the heart of Eastport, where timeless architecture meets modern comfort and one of the neighborhood's most coveted amenities-abundant off-street parking. Rich in history and craftsmanship, the home showcases an antique fireplace mantel with a hand-carved frieze, artisan wrought iron banister and fencing created by a metalsmith and co-founder of the renowned Niermann Weeks design atelier, elegant dentil molding, and wide lintels that reflect the character of a bygone era. A thoughtfully designed 1986 renovation introduced a two-story addition and reconfigured the home around a central hallway, creating the exceptional floor plan enjoyed today while preserving its historic charm. The kitchen was beautifully renovated in 2022 by designer Nicole Rauzi of Chromas Kitchens with updated custom cabinetry, fixtures, and appliances, blending contemporary function with classic style. Plantation shutters throughout the home add timeless elegance and refined privacy. French doors open from the living room to a newly completed screened porch (2026), overlooking a private garden filled with mature perennials and seasonal blooms-an inviting extension of the home's living space. Offering three bedrooms and three-and-a-half baths, the home also features updated bathrooms, including a first-floor bath renovated in 2022 and a second-floor bath updated in 2017. Equally impressive is the detached garage and guest retreat. Rarely found in Eastport, the property provides six off-street parking spaces, including a two-car garage and four additional dedicated spaces. Above the garage, a finished guest suite with a full bath and its own mini-split HVAC system (2022) offers exceptional flexibility as a private home office, guest quarters, studio, or potential income-producing space. Additional improvements include Hardie Plank siding (2020), washer and dryer (2022), and irrigation system (2017). Recognized on the prestigious Annapolis Home & Garden Tour, this exceptional residence places you just moments from Eastport's celebrated restaurants, marinas, boutiques, galleries, and waterfront parks, with easy access across the Spa Creek Bridge to Historic Downtown Annapolis. A home where historic character, thoughtful updates, and an unmatched Eastport lifestyle come together in one extraordinary offering.