27 Wigwam Road, Nantucket MA

Tucked near one of Nantucket’s most beloved South Shore beaches, this 5-bedroom, 4.5-bath upside-down beach house is a true coastal gem. Designed for both comfort and style, the home features soaring wood-beamed ceilings, an intricately inlaid compass rose in the hardwood floors, and a classic widow’s walk offering panoramic ocean views. With three distinct living areas—one on each level—plus a loft, there’s room for everyone to spread out or come together. The well-appointed kitchen opens seamlessly to the dining area and sunny second-floor decks, perfect for entertaining. With room for a pool, stunning ocean-facing vistas, and exceptional character inside and out, this home offers the ultimate Nantucket lifestyle.

Floor 1: The first floor of this beach house, set in a quiet and laid-back location, features a private en-suite bedroom, two generously sized guest rooms that share a full hall bath, and a versatile fourth room perfect as an office, library, or overflow sleeping space. Beautiful hardwood floors run throughout, adding warmth and coastal character.,

Floor 2: The second floor is designed to take full advantage of the ocean breezes and ocean views, with a spacious dining deck that invites al fresco entertaining. Anchoring this level is the primary suite, complete with a walk-in closet and a private bath. Soaring cathedral ceilings with exposed wood beams span the open-concept living spaces, including a custom kitchen with built-in cabinetry and generous counter space, a sunlit dining area, and a cozy living room with a wood-burning fireplace. A tucked-away powder room just off the main stair landing offers added convenience for guests. Mahogany ladder leads to loft space to access the widows walk to take in panoramic views all the way to Sankaty lighthouse and beyond.,

Floor 3: Loft space accessible via mahogany ladder with access to the recently restored widows walk.

The fully finished lower level offers a spacious third living area, a large bedroom comfortably sized for a king bed, and a full bath—ideal for guests or extended family. A separate laundry room handles beach towels and gear with ease, while tucked-away utilities keep things running smoothly behind the scenes.