Welcome to 99 Old Academy Road, a distinguished Cape originally reimagined by local architect Richard Swann and thoughtfully expanded in 2019 by Alex Esposito. Arched-top dormers elevate the architecture, blending tradition with luxury. This residence offers 6 bedrooms plus a private two-level guest suite, 7 full / 3 half baths, all set on 2+ acres in lower Greenfield Hill. At the heart of the home, the kitchen offers an open layout with a spacious dining area, custom cabinetry, a floor-to-ceiling glass wine display, and walk-in pantry. The kitchen flows seamlessly onto a bluestone patio with a double-sided fireplace, perfect for indoor-outdoor living. The kitchen leads to the lower level, featuring a stone bar in the game room, a 10-seat cinema, and ample storage. The family room, with its built-ins, poolside views, and gas fireplace, offers an inviting year-round retreat, the main level also includes a private office. Upstairs, every bedroom is paired with its own private bath, each with a unique design. The custom mahogany library serves as a passage to the East Wing, where the main level offers a gym, poolside lounge, & outdoor shower, while the upper-level features three additional en-suite bedrooms and a second laundry room. Outdoors, enjoy wraparound mahogany decks, multiple bluestone patios, a heated pool, volleyball court, pergola gardens, and fruit trees. 99 Old Academy Road isn't just a home, it's a lifestyle of elegance, comfort, and unforgettable spaces.