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37 Sankaty Head Road, Nantucket, MA

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AN ICONIC 6.5 ACRE+/OCEANFRONT COMPOUND 3 7 S A N K AT Y H E A D R O A D , N A N T U C K E T, M A


COASTAL LIVING ON NANTUCKET ISLAND

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Perched high above the Atlantic on Nantucket’s

totaling 10,041 SF+/-, including a 8,300 SF+/- main

storied Sconset Bluff, 37 Sankaty Head Road is

residence and a 1,741 SF+/- finished guest house

a rare offering of scale, privacy, and panoramic

with an attached two-car garage. Across the

coastal beauty. Originally designed by Lyman

compound lie a total of 8 bedrooms and 8 full

Perry in 2006 and masterfully reimagined in 2024

and 2 half bathrooms, thoughtfully designed to

by BPC Architecture, with construction by Clarke

accommodate both grand-scale entertaining and

Brothers, this extraordinary turnkey compound

intimate coastal retreat, along with a private path

seamlessly blends timeless island architecture with

leading directly to the beach below.

refined modern living. Set on approximately 6.5 acres+/-, the estate unfolds across two structures

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7 5 0 ' O F O C E A N F R O N TAG E + / -

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Commanding sweeping 270-degree views of the Atlantic Ocean and 750’ of ocean frontage, Sesachacha Pond, and the iconic Sankaty Head Lighthouse, the estate occupies one of the island’s most breathtaking vantage points. From sunrise over the ocean to the ever-changing light across the bluff, the setting is nothing short of extraordinary.

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P R I VAT E B E A C H PAT H

750' OF OCEANSIDE F R O N TAG E + / -

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ELEVATED ON NANTUCKET’S EASTERN SHORE

Positioned on the eastern end of Nantucket, the property offers a rare combination of privacy and accessibility. It is located less than ¾ of a mile+/to Sankaty Head Lighthouse and approximately 2.5 miles+/- to the Siasconset Village Market and beloved seasonal dining.

MAIN RESIDENCE

GUEST HOUSE

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Scenic bluff trails and pristine beaches are moments away, while Nantucket Town—with ferry access, restaurants, and boutiques—is just a short drive.

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FEATURES & AMENITIES 3 7 S A N K AT Y H E A D R O A D , N A N T U C K E T, M A CO-EXCLUSIVE

|

$26,850,000

ORIGINAL ARCHITECT | 2006 LY M A N P E R R Y

PROPERTY OVERVIEW

R E N O VAT I O N A R C H I T E C T | 2 0 2 4 BPC ARCHITECTURE

• 750' of Ocean Frontage+/-

BUILDER CLARKE BROTHERS

• 6.5 Acres+/-

• Oceanfront on Sconset Bluff

• 270-Degree Views of the Atlantic Ocean

• Turnkey Compound • 2 Structures

LO C AT I O N

• Elevated on Sconset Bluff on Nantucket • Unobstructed Views of the Atlantic Ocean, Sesachacha Pond, & Sankaty Head Light house • Less than ¾ of a Mile+/- to Sankaty Head Lighthouse • 2.5 Miles+/- to Siasconset Village Market & Seasonal Dining • Access to Scenic Bluff Trails • Short Drive to Nantucket Town, Ferry Access, Restaurants, & Boutiques • Eastern End of the Island, Offering Privacy & Coastal Surroundings

• 10,041 SF+/- in Total — Main Residence: 8,300 SF+/— First Level: 3,300 SF+/— Second Level: 2,500 SF+/— Lower Level: 2,500 SF+/— Guest House: 1,741 SF+/- (Above Grade) — First Level: 1,144 SF+/— Second Level: 597 SF+/— Lower Level: 716 SF+/- (Unfinished) — Attached 2-Car Garage: 520 SF+/• 8 Bedrooms in Total — Main Residence: 6 Bedrooms — Guest House: 2 Bedrooms • 8 Full & 2 Half Bathrooms in Total — Main Residence: 6 Full & 1 Half Bathrooms — Guest House: 2 Full & 1 Half Bathrooms • Private Path to Beach

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I N T E R I O R F E AT U R E S

• Wood Flooring • Custom Millwork Throughout • Architectural Ceilings • High-End SubZero Appliances • Recessed Lighting

E X T E R I O R F E AT U R E S

• Outdoor Kitchen with Refrigerator, Ice Maker, BBQ, Pizza Oven, Burner • Plunge Pool Wrapping a Sunken Firepit • 2 Outdoor Showers • Pergola Covered Dining Area • Wrap-Around Porch • Guest House • Landscaped Grounds

MECHANICAL / TECHNICAL

• Central Air Conditioning • Heat Source: Propane • Water Source: Private Well • Irrigation System • Full House Generator • 5 Wood-Burning Fireplaces (4 Main House, 1 Guest House)

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OUTDOOR LIVING

LIFE AT THE WATER'S EDGE Designed to embrace its extraordinary setting, the grounds offer a collection of resort-caliber amenities framed by panoramic ocean and pond views.

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A plunge pool wraps around a sunken firepit, creating a dramatic focal point for evening gatherings beneath the coastal sky.

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SITTING AREA

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A pergola-covered dining area and fully equipped outdoor kitchen—complete with refrigerator, ice maker, BBQ, pizza oven, and burner—provide an exceptional setting for al fresco entertaining.

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Two outdoor showers, landscaped grounds, and a private path leading directly to the beach below reinforce the home’s seamless connection to nature.

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P R I VAT E BEACH PAT H

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MAIN RESIDENCE | FIRST LEVEL

GRAND LIVING FRAMED BY THE ATLANTIC Designed with every principal room oriented toward the water, the first level captures the essence of elevated coastal living. A covered wrap-around porch encircles the home, while French doors from the living spaces open seamlessly to terraces and sweeping ocean vistas, dissolving the boundary between indoors and out.

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LIVING ROOM

The living room opens beneath a coffered ceiling, where generous seating gathers around a classic wood-burning fireplace. French doors and tall windows bring in natural light and lead to the surrounding outdoor spaces.

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At the center of the room, a long dining table anchors the open living space, naturally positioned between the surrounding seating areas and expansive windows.

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A secondary sitting area offers a quieter place to settle in, where soft textures and a traditional fireplace create a relaxed retreat with sweeping water views beyond.

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At the heart of the home, the eat-in kitchen features a large center island with bar seating and a sitting area with wood-burning fireplace and dedicated coffee station, creating a natural gathering space infused with warmth and light, with an adjacent breakfast area overlooking the water.

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E AT- I N K I T C H E N

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SITTING AREA

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BREAKFAST AREA

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Privately positioned on this level, the first-floor primary suite serves as a serene retreat. A wood-burning fireplace, two closets, and French doors leading to a private terrace with outdoor shower offer both comfort and seclusion.

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The en-suite bath is appointed with a large shower, double vanity, and soaking tub.

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MAIN RESIDENCE | SECOND LEVEL

A PRIVATE SANCTUARY ABOVE THE BLUFF

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The second-level primary suite is defined by light, scale, and sweeping horizon views. French doors open to a private terrace overlooking the Atlantic, creating a serene retreat above the coastline.

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PRIMARY TERRACE VIEWS

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The spa-like primary bath offers a refined and restorative setting, featuring a double vanity, water closet, soaking tub, and an expansive dual-head walk-in shower.

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Two additional guest en-suites, each with custom built-ins, generous closet space, and beautifully appointed baths, provide comfort and privacy. One guest suite features its own private terrace, offering yet another vantage point to take in the seaside setting.

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One guest suite features its own private terrace, offering yet another vantage point to take in the coastal setting.

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MAIN RESIDENCE | LOWER LEVEL

RECREATION & RETREAT The finished lower level offers a flexible extension of the home’s living space. A wet bar with dual full-height wine refrigerators and ample storage anchors a comfortable sitting room ideal for gathering.

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WET BAR

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A private gym with mirrored wall, bunk room, additional guest bedroom, two full bathrooms, laundry room, and dedicated mechanical space complete this level, accommodating extended stays and multigenerational living with ease.

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GUEST BEDROOM

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BUNK ROOM

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GUEST HOUSE

INDEPENDENT LIVING WITH COASTAL CHARM The 1,741 SF+/- guest house is fully finished and designed to provide autonomy while maintaining cohesion with the main residence.

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On the first level, an open-concept living room with wood-burning fireplace flows into the kitchen and breakfast area, creating a welcoming space for guests.

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KITCHEN AREA

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A guest en-suite bedroom, powder room, laundry area, and direct access to the attached two-car garage ensure comfort and convenience.

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The second level features an additional en-suite guest bedroom, offering privacy and flexibility for hosting family and friends.

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MAIN RESIDENCE FIRST LEVEL • Covered Wrap-Around Porch • Entry Foyer — Powder Room • Mudroom — Laundry — Closet Storage • Living Room — Wood-Burning Fireplace — French Doors to Wrap-Around Porch • Formal Dining Room

BATH ROOM

— Wood-Burning Fireplace

MASTER BEDROOM

— French Doors to Wrap-Around Porch • Breakfast Area — Wet Bar with Wine Storage CL

— French Doors to Wrap-Around Porch

CL

CL

• Eat-In Kitchen — Large Center Island with Bar Seating — Sitting Area with Wood-Burning Fireplace & Coffee Station — French Doors to Wrap-Around Porch • First Level Primary En-Suite — Wood-Burning Fireplace — French Doors to Private Terrace with Outdoor Shower — Two Closets — Primary En-Suite Bathroom — Large Shower — Double Sink Vanity — Soaking Tub

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CL


L

L

PATIO TERRACE

DINING ROOM

KITCHEN/ SITTING ROOM BAR

HALLWAY

MUD ROOM

ENTRY W/D LIVING ROOM PR

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MAIN RESIDENCE SECOND LEVEL • Second Level Primary En-Suite — French Doors to Private Terrace with Ocean Views — Walk-in Closet — Primary En-Suite Bathroom — Laundry — Double Sink Vanity — Water Closet — Expansive Double Walk-In Shower with Dual Shower Heads — Soaking Tub — Private Terrace • 2 Guest En-Suites BEDROOM 4

— Private Spa-Like Bathrooms — Built-in Dressers — Ample Closet Space — 1 with Private Terrace CL

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CL


BALCONY

CL BEDROOM 3

CL

BATH ROOM

BATH ROOM

BALCONY

PRIMARY BEDROOM

LANDING

PRIMARY DRESSING ROOM

PRIMARY BATHROOM

BALCONY

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MAIN RESIDENCE LOWER LEVEL • Wet Bar with 2 Full Height Wine Refrigerators, Sink, & Ample Storage • Laundry Room • Private Gym with Mirrored Wall • 2 Full Bathroom’s • Sitting Room • Bunk Room • Guest Room • Mechanical Room

MECHANICAL STORAGE

BUN BATH ROOM

HALL

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GUES


SITTING AREA BATH ROOM GYM

NK ROOM

PR

ST ROOM

KITCHEN

LAUNDRY ROOM

MECHANICAL

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KITCHEN

LAUNDRY ROOM

MECHANICAL

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GUEST HOUSE FIRST LEVEL BATH ROOM

BEDROOM

• Open Concept Main Living

• Guest En-Suite Bedroom

Space

• Hallway

— Living Room with

— Powder Room

Wood-Burning

— Laundry

Fireplace

— Access to Attached

— Kitchen & Breakfast

2-Car Garage

Space

PATIO

LOUNGE

BEDROOM

HALL

GARAGE

BATHROOM

W/D HALL PR

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HALL

GUEST

GUEST HOUSE SECOND LEVEL • Guest En-Suite Bedroom

BATH ROOM BEDROOM

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SITE PLAN

WAY

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5'59"

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3 7 S A N K AT Y H E A D R OA D I S A G E N E R AT I O N A L O F F E R I N G D E F I NED BY RARE ACREAGE, ICONIC VIEWS, AND COMPREHENSIVE 2024 R E N O VAT I O N . B L E N D I N G A R C H I T E C T U R A L P E D I G R E E W I T H M O D E R N R E F I N E M E N T, T H I S O C E A N F R O N T C O M P O U N D S TA N D S AS ONE OF NANTUCKET’S MOST C O M P E L L I N G A N D C O M P L E T E E S TAT E S .

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LAURA KLEIN PORTFOLIO MANAGER

917.626.9773 | LAURA@BESPOKEREALESTATE.COM

HAMPTONS: 631.500.9030 | NYC: 212.542.4582 | SOUTH FLORIDA: 305.800.9030

BESPOKEREALESTATE.COM

© 2026 BESPOKE REAL ESTATE LLC (“BESPOKE”), A LICENSED REAL ESTATE BROKER. BESPOKE’S TERMS AND CONDITIONS AND MAY BE CHANGED AT ANY TIME. BESPOKE DISCLAIMS ANY AND ALL WARRANTIES, EXPRESS OR IMPLIED, INCLUDING, BUT NOT LIMITED TO, WARRANTIES AS TO THE RELIABILITY, ACCURACY OR CURRENCY OF ANY INFORMATION, IMAGES AND/OR OTHER CONTENT HEREIN. BESPOKE FULLY SUPPORTS AND COMPLIES WITH THE FAIR HOUSING ACT, EQUAL HOUSING OPPORTUNITY ACT AND RELATED STATE AND LOCAL LAWS THAT PROHIBIT DISCRIMINATION.


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37 Sankaty Head Road, Nantucket, MA by Bespoke Real Estate - Issuu