5 Iconic Nantucket Retreats and a Beacon Hill Townhouse

Steps from the beach in Brant Point, one of Nantucket’s most coveted seaside neighborhoods, this beautifully appointed four-bedroom home balances classic island charm with modern comfort. A gracious wrap-around porch sets an easy rhythm from the start, drawing you into a light-filled interior arranged for both quiet mornings and lively evenings. Thoughtful details and a natural flow between indoor and outdoor living spaces make everyday life feel effortless, with town close by when you want it. Outside, a private patio is tailored for lingering: dedicated dining and lounge areas, a gas grill for simple suppers, and an outdoor shower for post-beach resets. Above it all, a rooftop widow’s walk crowns the home with picturesque harbor views and sunsets that turn the horizon into a daily ritual.

Along Nantucket’s historic Orange Street, this residence balances timeless character with modern comforts and an easy, walkable rhythm to town. The first floor is organized around an open-concept kitchen, dining, and living area, complemented by a cozy family room and a study with a wet bar that opens to a private bluestone patio—an inviting extension for quiet mornings or evening gatherings. An ensuite bedroom, along with a mudroom, laundry, and pantry, brings day-to-day ease. Upstairs, four bedrooms include a primary suite with vaulted ceilings, a walk-in closet, and a spa-like bath, plus additional family and hall baths. A finished third floor adds extra sleeping space and access to the widow’s walk, where views stretch over Nantucket Harbor. Built by Oak Development, it’s a home designed for both retreat and connection.

Commanding panoramic views of the Atlantic Ocean and White Goose Cove, 8 Sheep Pond Road is a coastal compound in Nantucket set on more than two acres, with protected conservation land as its backdrop. The property pairs a five-bedroom main house with a three-bedroom guest house, plus a pool house studio and a pool, all positioned for sweeping southwest-facing ocean views and unforgettable sunsets. Fully furnished and comprehensively renovated in 2021, the interiors were reimagined in warm earth tones, natural textures, and timeless materials for a refined, welcoming feel. Walls of windows frame the scenery from nearly every room, strengthening the connection between indoor and outdoor living. Days unfold across decks and a sprawling lawn—entertaining, gathering by the pool, or simply watching the water and landscape shift with the light.

Originally built as a historic townhouse in Beacon Hill, this residence has been thoughtfully restored to bring the flow and luxury of modern living into a timeless setting. A dramatic entry frames sweeping views into an open floorplan, where a custom gas fireplace and built-in banquette set the tone for easy entertaining. In the kitchen, Arabescato Vagli detailing takes center stage, paired with spectacular millwork and an abundance of sunlight.

Steps from the beach in Brant Point, 12 Willard Street pairs a prime Nantucket address with a beautifully renovated upside-down layout designed for light and ocean breezes. The open-concept second floor brings together a gourmet kitchen with high-end appliances, a dining area, and a living room that extends seamlessly to a private deck—made for morning coffee, easy entertaining, or a quiet reset after the sand. Four spacious bedrooms and four and a half bathrooms include three king suites plus a custom bunk room, offering comfort and privacy for family and guests alike. Premium finishes throughout add a polished, contemporary feel while keeping a sense of classic island charm. A charming patio and outdoor shower round out the everyday pleasures, with downtown shopping and dining just a stroll away.