Imagine owning a piece of unparalleled prestige, where luxury meets the raw beauty of nature. From the historic charm of Cambridge, with its proximity to Harvard and serene, landscaped gardens, to the breathtaking coastal havens of Nantucket, boasting private beaches and panoramic ocean views, these four extraordinary estates redefine exclusivity. Priced between $7.5M and $35M, they offer rare opportunities—whether through grandfathered structures or iconic locations—catering to those who seek privacy, prestige, and a profound connection to their surroundings, be it urban-academic or quintessential island life.
Secluded Luxury Estate | $35,000,000


Gail Roberts & Gail Roberts

Gail Roberts & Gail Roberts
Situated just a mile from the historic charm of Harvard, this legacy estate unfolds across over an acre of meticulously landscaped grounds, presenting a rare blend of privacy and timeless elegance. The gardens, a living canvas, evolve with the seasons, weaving a vibrant tapestry of color and texture that captivates the senses year-round. Each corner of the property reveals a new botanical delight, creating an serene retreat for quiet reflection or intimate gatherings. Beyond its natural beauty, the estate offers a profound sense of seclusion, a sanctuary where one can escape the pace of everyday life while remaining close to the cultural and academic heartbeat of the area. This is more than a home; it’s a haven where luxury meets nature, inviting a lifestyle of tranquility and connection to the land in one of the region’s most coveted settings.
- Price:
- $35,000,000
- Size:
- 8,163 sq ft
- Contact:
- Gail Roberts & Gail Roberts, Coldwell Banker, 617.844.2712 , 617.780.4354
52 Monomoy Rd | $34,500,000


Gary Winn & Morgan Winn

Gary Winn & Morgan Winn
Positioned along one of Nantucket’s most sought-after harborfront locations, this remarkable 1.25-acre estate offers an unrivaled coastal lifestyle with sweeping panoramic views. Gaze across the harbor from Town to Brant Point and Coatue, where sunsets paint the water, sailboats drift gracefully, and seasonal fireworks illuminate the sky. At the heart of this property lies a stately seven-bedroom, six-and-a-half-bath main residence, subtly elevated to ensure breathtaking vistas from every level. A spacious two-car garage with guest quarters above adds versatility, while a charming boathouse perches at the water’s edge, a rare feature with grandfathered proximity to the coastal bank. With approximately 175 feet of direct waterfront and a private sandy beach accessed via a gently sloping drive, this estate seamlessly blends luxury with the serene beauty of island living, creating a truly exceptional retreat.
- Price:
- $34,500,000
- Size:
- 6,875 sq ft
- Contact:
- Gary Winn & Morgan Winn, Maury People Sotheby’s International Realty, 508.330.3069 , 508.330.3069
113 Eel Point Rd | $17,750,000


Gary Winn & Morgan Winn

Gary Winn & Morgan Winn
Situated along the serene waterfront, this exquisite beachfront home offers a lifestyle defined by tranquility and natural beauty. The open-concept living space effortlessly connects the kitchen, dining, and living areas, creating an inviting environment for gatherings or quiet evenings. French doors lead to a spacious patio with a private walkway to the beach, where breathtaking ocean views await. The first floor features a luxurious primary suite with an ensuite bathroom and a thoughtfully designed walk-in closet, while a charming twin room with its own ensuite and outdoor shower adds convenience. Upstairs, a queen bedroom with a private bathroom and a cozy living area with a balcony capture stunning coastal vistas. Additional bedrooms, a well-appointed hall bathroom, and a finished gym in the basement ensure every need is met. This coastal retreat blends elegance with the allure of seaside living.
- Price:
- $17,750,000
- Size:
- 4,299 sq ft
- Contact:
- Gary Winn & Morgan Winn, Maury People Sotheby’s International Realty, 508.330.3069 , 508.330.3069
45 Brewster Rd | $7,500,000


Shellie Dunlap

Shellie Dunlap
Tucked away behind a towering privet hedge in the heart of Monomoy, this rare Nantucket estate offers a private sanctuary of unparalleled serenity. Encompassing over 1.2 acres bordering the State Forest, the property invites relaxation with its meticulously manicured gardens, mature trees, and a sparkling in-ground pool. The sprawling lawn beckons for family gatherings, whether it’s a game of croquet, a barbecue on the bluestone patio, or storytelling around the expansive firepit. Inside, the main house, fully renovated in 2023, exudes chic sophistication with four bedrooms, three bathrooms, and a gourmet kitchen featuring a large island, high-end appliances, and a cozy fireplace nook. A separate guest house, also updated in 2023, provides additional comfort with three bedrooms, two bathrooms, a living area, kitchenette, and a den overlooking the lush backyard. This estate redefines tranquil island living.
- Price:
- $7,500,000
- Size:
- 3,459 sq ft
- Contact:
- Shellie Dunlap, Lee Real Estate, 508.901.9890











