5 Nantucket and Cape Cod Estates with Iconic Waterfront Views

Along the water’s edge on Monomoy Road, this 1.25-acre Nantucket estate commands one of the island’s most coveted harborfront settings, with sweeping panoramic views from Town across the harbor to Brant Point and Coatue. Days unfold to the rhythm of sailboats gliding by, while sunsets and seasonal fireworks turn the horizon into a nightly ritual. Slightly elevated for sightlines from every floor, the seven-bedroom, six-and-a-half-bath main residence anchors the property, joined by a spacious two-car garage with guest accommodations above. At the shoreline, a charming boat house sits essentially on the coastal bank, a pre-existing nonconforming use that underscores the rarity of this site. With approximately 175 feet of direct waterfront, a gently sloping drive leads down to a private sandy beach and an easy, unrepeatable connection to the harbor.

Commanding views from high on the Sconset Bluff, 37 Sankaty Head Road unfolds as a private family compound with sweeping, unobstructed vistas of the Atlantic Ocean, Sesachacha Pond, and Sankaty Light. Set across six acres, the estate pairs a main residence with a two-bedroom guest house, creating space for gathering and retreat. Outdoors, a singular water feature anchors the experience, with a fire pit and seating area encircled by a wraparound pool—an easy place to take in sunsets and sunrises over the ocean. Originally constructed in 2006 and thoughtfully renovated in 2024, the interiors balance extraordinary architectural details with museum-quality finishes. Light-filled rooms are framed by intricate box trim and coved ceilings, solid panel doors, and bespoke craftsmanship, all in a serene palette of sandy beiges, coastal grays, and nautical blues for a quietly elegant daily rhythm.

Down a quiet turn off Hummock Pond Road, 15 Deer Run unfolds across 1.84 private acres at the edge of Nantucket’s cherished natural corridor. Conceived and delivered by Aerie Group, with interiors by Embarc Design and grounds by Atlantic Landscape, the residence reads as a study in considered luxury—more discovered than announced. Six bedrooms and seven full baths are complemented by a dedicated gym with sauna, with flexibility to convert the gym into a seventh bedroom. Outdoors, a heated pool and hot tub extend the day well beyond summer. Inside, custom white oak shiplap millwork flows through the first floor, setting a warm, edited tone that feels distinctly of the island. A fully self-sufficient solar array and a brand-new 8-bedroom septic system underscore the home’s forward-thinking infrastructure. Delivered fully furnished and curated, every room arrives complete for effortless living.

Along the water’s edge in Oyster Harbors, this gated Cape Cod estate commands 450 feet of frontage, a private beach, and sweeping views across Cotuit Bay and North Bay—an ideal backdrop for sunset evenings. Inside, a grand foyer with vaulted ceilings and expansive windows keeps the horizon in constant view. Open-concept living areas flow from a gracious living room to a dining room warmed by a fireplace and custom built-ins, with a sophisticated sitting area for easy entertaining. A private library, reached by a spiral staircase, overlooks the main level and the water beyond. The chef’s kitchen pairs a granite center island and custom built-ins with a breakfast nook wrapped in picture windows. The first-floor primary suite offers patio access, a walk-in closet, and a spa-like bath. Outdoors, landscaped grounds feature a waterside pool, fire pit, outdoor shower, and private dock.

Steps from the shoreline, 4 Cathcart Road offers an expansive parcel in one of Nantucket’s most peaceful enclaves, envisioned for a private compound shaped by the land’s generous acreage. The site is described as having potential to accommodate a main residence and guest cottage, along with a full suite of lifestyle amenities—from a swimming pool to a tennis court—set within a serene natural landscape. Just 700 feet from shoreline access, it also carries the potential for elevated vistas of the harbor and striking evening skies from a future second floor. Unique contours create a dynamic canvas for thoughtful site planning, while bordering Nantucket Conservation Foundation land supports enduring privacy and a close connection to untouched surroundings. An approved Notice of Intent is already in place, and an on-site viewing platform hints at what could unfold here.

Size: 7.00 acres