Nestled in the exclusive coastal haven of Nantucket, MA, five extraordinary estates redefine luxury living. From a waterfront compound with sweeping Atlantic Ocean views to a historic equestrian estate steeped in 18th-century charm, each property offers expansive spaces, seamless indoor-outdoor design, and unparalleled craftsmanship. Located in prime spots like Cisco and the prestigious Cliff neighborhood, these homes blend privacy with convenience, catering to diverse high-end lifestyles—whether you seek oceanfront serenity, modern coastal elegance, or rural heritage. Discover what makes each of these rare properties a masterpiece in its own right.
2 Marion Avenue | $24,950,000
Set against the serene backdrop of Cisco, Nantucket, this breathtaking waterfront estate spans nearly two acres, offering unparalleled 180-degree views of the Atlantic Ocean. With direct sightlines to one of the island’s most coveted beaches, this front-row property encompasses over 6,500 square feet of sophisticated living space. Six bedrooms, six full baths, and three half baths provide ample room for family and guests, while a two-story guest house and attached garage add versatility. Designed to harmonize indoor and outdoor spaces, the estate boasts multiple decks, an indoor/outdoor sound system, and a spacious outdoor shower. A gourmet kitchen, complete with high-end appliances and a walk-in pantry, serves as the heart of entertaining. Additional luxuries include a wine cellar, wet bars, and an enclosed gym. Positioned near Bartlett’s Farm, Cisco Beach, and Miacomet Golf Course, this estate promises a lifestyle of coastal elegance and endless island exploration.
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Price: $24,950,000
Contact: Gary Winn & Bernadette Meyer, Maury People Sotheby’s International Realty, 508.330.3069
6 8 Sherburne Turnpike | $22,500,000
Set against the serene waterfront of Nantucket’s prestigious Cliff neighborhood, this distinguished estate at 6 & 8 Sherburne Turnpike offers a rare blend of privacy and coastal elegance across two conforming lots. Masterfully crafted by the renowned Hehir Group, the property encompasses a main residence, guest cottage, and garage studio, thoughtfully arranged around a heated pool, spa, and sauna. The meticulously renovated main house spans 5,572 square feet, featuring five bedrooms, a bunk room, and a harmonious balance of four full and three half baths. Meanwhile, the 2,360-square-foot guest cottage provides two bedrooms and three full baths for gracious accommodations. A versatile garage studio adds 572 square feet of finished space. With mature landscaping, fieldstone walls, a roof walk showcasing harbor views, and proximity to Steps Beach and Historic Downtown Nantucket, this estate embodies the quintessential island lifestyle.
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Price: $22,500,000
Contact: Gary Winn & Morgan Winn, Maury People Sotheby’s International Realty, 508.330.3069, 508.332.9088
Dream Waterfront Home | $17,750,000
Tucked away in a serene countryside setting, this 29-acre equestrian estate captivates with its timeless beauty and rich history. At its heart stands a remarkable 1775 fieldstone home, spanning 8,500 square feet, where original American plank Chestnut floors, hand-forged hinges, and four wood-burning fireplaces evoke 18th-century charm, seamlessly paired with modern comforts. With over five bedrooms and vintage bathrooms adorned with Moravian tile, the residence brims with character. Sunlit spaces like the enchanting sunroom with bay windows offer breathtaking views of the sprawling grounds, while a practical kitchen boasts industrial sinks and classic tiling.
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Price: $17,750,000
Contact: Gary Winn & Morgan Winn, Maury People Sotheby’s International Realty, 508.330.3069, 508.332.9088
Multi Generational Estate Ideal For Entertaining | $12,850,000
Tucked away on 2.45 acres of serene countryside, 24 Flintlock emerges as a remarkable family compound, bordered by the tranquil Nantucket Land Bank conservation land for unmatched privacy. This expansive estate boasts a six-bedroom main house, a charming three-bedroom guest cottage, a pool house, and a garage with a studio apartment, all set amidst impeccably manicured grounds. The outdoor haven is a true highlight, perfect for gatherings, with a 20’ x 36’ heated Gunite pool framed by elegant bluestone, a spacious pool cabana blending indoor and outdoor living, a striking brick fireplace, and an outdoor kitchen with bar seating for eight. With ample space to add a tennis court, the property offers endless possibilities for leisure. Thoughtfully designed by Trisha Wynn Designs and fully furnished, this turnkey retreat awaits a family ready to craft cherished Nantucket memories.
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Price: $12,850,000
Contact: Chris Kling & Kate Kling, Pepper Frazier Real Estate, 508.446.0444, 617.694.8147
The One For Beach Living Private Retreat Near Surfside Beach | $4,495,000
Set against the tranquil backdrop of a waterfront haven, this captivating retreat at 16 Gladlands in the sought-after Surfside area of Nantucket offers an idyllic escape on nearly two private acres. Bordering protected Land Bank land, the estate promises unparalleled privacy and serenity, enveloped by lush, mature landscaping. Designed for seamless outdoor living, the sprawling yard invites lawn games and leisurely afternoons, while a pristine pool and spa beckon for relaxation. Two expansive porches and an outdoor fireplace create perfect settings for evening gatherings, and the screened-in porch captures the golden glow of sunset. A nearby bike and walking path leads to the refreshing shores of Surfside Beach, blending convenience with nature. With ample space for future expansion, this property embodies the essence of a quintessential Nantucket summer, where tranquility and coastal charm intertwine effortlessly.
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Price: $4,495,000
Contact: Susan Chambers, Maury People Sotheby’s International Realty, 508.560.0671
