296 Halsey Rd, Annapolis, MD 21401

From the street, its charm is immediate, but step inside and the amount of space, functional layout and flexibility of the home quickly become the surprise. Well loved and carefully improved, it balances original character with meaningful updates throughout. A welcoming entry foyer sets the tone with a custom built-in bench and storage, adding character while keeping everyday comings and goings organized. From here, the home opens into the fully renovated kitchen, where upscale finishes pair with a functional layout and easy connection to the dining area. The open-concept dining and large family room create a natural flow for both everyday living and entertaining, with the family room anchored by an ashlar-cut sandstone fireplace with a raised flagstone hearth and a large bay window overlooking the front yard. Down the hall is the primary suite, which includes a beautifully renovated en suite bath, while two additional bedrooms share a large bathroom with convenient double-sink vanity. The lower level is where the home's versatility really comes into focus. It has comfortably served as a long-term guest suite, with a quasi-kitchenette, full bathroom and dedicated home office space. The oversized living room and adjacent living space were just renovated in 2026, creating even more room to gather, work, host guests or spread out. There is a 6th bedroom adjacent to the kitchenette that has a myraid of potential uses: home gym, hobby room, home theater space or storage. A full walkout leads directly to the patio, where overhead string lights make it an inviting extension of the living space. Set on a rare double lot just shy of a half acre, 296 Halsey offers a generous amount of outdoor space and established landscaping that changes with the seasons. Mature flowering pink magnolias fill with blossoms in the spring, followed by crepe myrtles bringing color later in the year. There is something intentional and worth noticing in every season, whether viewed from the bay window, beneath the front-yard tree swing or from the backyard patio. Since purchasing the home, the current owners have invested significantly in 296 Halsey while taking great care of the character that was already here. The result is a home that feels genuinely well loved: spacious without losing its charm, updated without losing its personality, and far more expansive than its first impression suggests. Updates worth noting for any savvy home buyer: HVAC replaced (2026), Basement Renovation (2026), Roof (2023) and Kitchen + Primary Suite full renovation (2022).