Homes for Sale in 02554

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  /24

  $2,495,000

  • 8 Beds
  • 6 Baths
  • 3,478 Sq Ft

  106 Old South Rd Unit A Unit B, Nantucket, MA 02554

  $2,495,000 – Exceptional 2-Unit Multi-Family Investment Opportunity Don’t miss this rare opportunity to own a versatile and beautifully maintained two-unit multi-family property in a prime location. Whether you're looking for a strong investment, multi-generational living, or the perfect live-in/rent-out setup, this property offers incredible flexibility and value. The front unit has been fully

  Joyce Montalbano Congdon & Coleman Real Estate

  106 Old South Rd Unit A Unit B, Nantucket, MA 02554
• 

  

  

  /21

  $3,295,000

  $200K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,802 Sq Ft

  321 Madaket Rd, Nantucket, MA 02554

  Escape to the tranquility of Madaket to this charming Nantucket retreat featuring a 2-bedroom main house and a separate studio garage apartment. Thoughtfully designed for comfort and coastal living, the home offers welcoming indoor spaces along with multiple outdoor areas perfect for enjoying the spacious yard, distant ocean and harbor views and iconic Madaket sunsets. Ideally located, you’re

  John Arena William Raveis Nantucket

  321 Madaket Rd, Nantucket, MA 02554
• 

  

  

  /19

  $4,995,000

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  44 Madequecham Valley Rd, Nantucket, MA 02554

  Step back in time to one of Nantucket’s last remaining 1940s waterfront beach houses. Set on an oversized parcel in 3-acre zoning, 44 Madequecham Valley Road offers an exceptionally unique opportunity to own waterfront of this vintage on a parcel of this scale. With a sweeping shoreline and direct water access, this property invites the creation of a private coastal retreat - whether fully

  Bernadette Meyer Maury People Sotheby's International Realty

  44 Madequecham Valley Rd, Nantucket, MA 02554
• 

  

  

  /19

  $2,395,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,305 Sq Ft

  38 Hooper Farm Rd, Nantucket, MA 02554

  Turnkey single-family opportunity! This newly renovated 5-bedroom, 4.5-bath home offers effortless living in a convenient location close to beaches, schools, bike paths, and Town. Once a classic Surfside cottage, it has been carefully relocated and beautifully repurposed, giving it new life. The property features three finished levels of sun-filled living space, ample parking, central AC, wood

  Rebecca Becker J Pepper Frazier Co.

  38 Hooper Farm Rd, Nantucket, MA 02554
• 

  

  

  /42

  $4,200,000

  $150K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 4,934 Sq Ft

  3 Monohansett Rd, Nantucket, MA 02554

  Hear the ocean! This exceptional residence is situated on a spacious 42,000-square-foot lot and was constructed in 2014, adhering to the highest standards of design, craftsmanship, and finishes. The home features three fully finished levels, showcasing a wood roof, custom millwork, and cabinetry throughout. Engineered oak flooring and premium tiles enhance the interior aesthetic, complemented by

  Penny Dey Atlantic East Nantucket Real Estate

  3 Monohansett Rd, Nantucket, MA 02554
• 

  

  /35

  $5,295,000

  $200K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 2,825 Sq Ft

  4 Sunset Hill Ln, Nantucket, MA 02554

  The full-scale renovation of Four Sunset Hill is complete and the property is ready for immediate enjoyment. Blending history and modern sophistication, this beautifully furnished home features five spacious bedrooms, each with walk-in closets and generous ensuite bathrooms. Additional highlights include an enclosed and western-facing sun porch, a cozy private den with a gas fireplace, and

  

  Jennifer Shalley Allen

  Fisher Real Estate

  4 Sunset Hill Ln, Nantucket, MA 02554
• 

  

  /81

  $3,975,000

  $25K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,472 Sq Ft

  27 Longwood Dr, Nantucket, MA 02554

  27 Longwood Drive is nestled on a sprawling 2.75-acre lot offering the ultimate in privacy and refined living. The generous foyer features a dramatic curved staircase leading to the second floor. This light-filled, charming, upside-down home features five bedrooms, three full bathrooms, and one half bathroom. The 2nd-floor open living space features a custom fireplace, a cathedral ceiling, a

  Debbie Willett Great Point Properties

  27 Longwood Dr, Nantucket, MA 02554
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  /43

  $5,999,999

  $505K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 1,772 Sq Ft

  26 Tennessee Ave, Nantucket, MA 02554

  This Madaket coastal retreat features 4 bedrooms, 2.5 bathrooms, and an upside-down layout designed to capture the views. Recently refreshed with new paint, flooring, and updated kitchen and baths, the home offers comfortable island living. A spacious two-car garage provides added convenience and storage for vehicles, beach gear, and boating equipment, and a newly installed 4-bedroom IA septic

  Michael O'Mara BHHS Island Properties Nantucket

  26 Tennessee Ave, Nantucket, MA 02554
• 

  

  /22

  $22,000,000

  • 4 Beds
  • 6.5 Baths
  • 3,415 Sq Ft

  15 Hallowell Ln, Nantucket, MA 02554

  Nestled at the end of a quiet lane, 15 Hallowell Lane, completely rebuilt in 2015, offers a waterfront setting with sweeping views of the harbor and beyond while providing updated and modern amenities. This special property features private stairs leading directly to the beach, providing effortless access to the sand and sea. Positioned for breathtaking sunsets, the home is a serene retreat just

  Greg McKechnie Great Point Properties

  15 Hallowell Ln, Nantucket, MA 02554
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  /6

  $3,500,000

  • Land
  • 19,998 Sq Ft
  • $7,623,611 per Acre

  12 Myles Standish St, Nantucket, MA 02554

  Positioned in the heart of Surfside, one of Nantucket’s most desirable south shore settings, this 20,000 SF lot offers exceptional potential for a custom build. With R-20 zoning allowing 12.5% ground coverage, the lot can accommodate up to 2,500 SF. Plans for a 3-bedroom I/A septic system have been approved. The property is just a short barefoot walk to the beach, with the possibility of

  Bernadette Meyer Maury People Sotheby's International Realty

  12 Myles Standish St, Nantucket, MA 02554
• 

  

  /28

  $9,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,367 Sq Ft

  56R Madequecham Valley Rd, Nantucket, MA 02554

  Completely reimagined, this modern oceanfront retreat blends state-of-the-art design with uncompromising quality. Positioned on the south shore, the three bedroom, three-and-a-half-bath main residence showcases walls of glass, seamless indoor-outdoor connections, and sweeping water vistas from nearly every room. Every detail reflects the highest level of quality and care, with finishes chosen for

  Bernadette Meyer Maury People Sotheby's International Realty

  56R Madequecham Valley Rd, Nantucket, MA 02554
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  /51

  $8,995,000

  $1M PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,676 Sq Ft

  1 Reeds Way, Nantucket, MA 02564

  A once in a life time opportunity to own this extraordinary six-bedroom, five-bathroom residence on nearly three acres of premier oceanfront, rising 45 feet above sea level with expansive decks soaring to approximately 65 feet. The result: uninterrupted, panoramic views of the Atlantic—capturing the island’s most breathtaking sunrises and sunsets from dawn to dusk. In 2025, the property underwent

  Morgan Winn Maury People Sotheby's International Realty

  1 Reeds Way, Nantucket, MA 02564
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  /26

  $4,295,000

  • 4 Beds
  • 4.5 Baths
  • 2,554 Sq Ft

  37 Union St, Nantucket, MA 02554

  Just minutes from Main Street, this antique 1800 home offers timeless charm with modern comforts. Set on a beautifully landscaped lot with mature plantings, the property features three coveted parking spaces. Inside, high ceilings and designer touches complement the character of five working fireplaces. Thoughtful upgrades in recent years blend seamlessly with the home’s historic details.

  Linda Bellevue Atlantic East Nantucket Real Estate

  37 Union St, Nantucket, MA 02554
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  /6

  $11,750,000

  $700K PRICE DROP

  • Land
  • 7.12 Acres
  • $1,650,281 per Acre

  4 Cathcart Rd, Nantucket, MA 02554

  Tucked away in one of the island’s most peaceful enclaves, this expansive parcel at 4 Cathcart Road presents a rare chance to craft a private compound unlike any other. With generous acreage (7+ acres), the land has potential to accommodate a main residence, guest cottage, and a full suite of lifestyle amenities — from a swimming pool to a tennis court — all set within a serene natural landscape.

  Morgan Winn Maury People Sotheby's International Realty

  4 Cathcart Rd, Nantucket, MA 02554
• 

  

  /4

  $1,650,000

  • Land
  • 20,041 Sq Ft
  • $3,586,177 per Acre

  11 Woodland Dr, Nantucket, MA 02554

  This half-acre vacant lot offers a prime building opportunity in the sought-after Surfside area. Recently cleared and landscaped with evergreen trees along the lot lines, the property provides both privacy and a ready canvas for development. Tucked away on a quiet cul-de-sac, the location offers easy access to Nantucket’s popular South Shore beaches, including Nobadeer, Fisherman’s, and Surfside.

  Stephen Maury Congdon & Coleman Real Estate

  11 Woodland Dr, Nantucket, MA 02554
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  /46

  $12,995,000

  $1M PRICE DROP

  • 5 Beds
  • 5 Baths
  • 4,224 Sq Ft

  105 Low Beach Rd, Nantucket, MA 02554

  Private. Peaceful. Pristine. Set on over 6 acres at the end of Low Beach, sits this ultimate retreat. This property enjoys breathtaking views over sand dunes to the ocean beyond, Tom Nevers pond and backs up to 300+ acres of conservation land. Sit on the front porch and take in the sea breeze and calming sounds of the pond and ocean, or relax out back in the private outdoor pool and outdoor

  John Arena William Raveis Nantucket

  105 Low Beach Rd, Nantucket, MA 02554
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  /47

  $7,195,000

  $300K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 4,930 Sq Ft

  18 Mill St, Nantucket, MA 02554

  An exceptional in-town opportunity, this home combines space, style, and convenience in a way rarely found downtown. The three-level main house is complemented by a separate studio, shed, and two-car parking. Outdoor living is designed for both relaxation and entertaining, with a covered porch, outdoor kitchen, gas fireplace, and multiple seating areas. Inside, thoughtful craftsmanship blends

  Bernadette Meyer Maury People Sotheby's International Realty

  18 Mill St, Nantucket, MA 02554
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  /65

  $26,850,000

  • 8 Beds
  • 10 Baths
  • 12,096 Sq Ft

  37 Sankaty Head Rd, Nantucket, MA 02554

  Commanding a presence high on the Sconset Bluff, this private family compound is inarguably one of the most stunning properties on Nantucket. Sited so as to enjoy sweeping, unobstructed views of the Atlantic Ocean, Sesachacha Pond, and Sankaty Light, the 6-acre estate includes a 12,000 square foot main residence, a 2 bedroom guest house, and a water feature. This water feature is unmatched with a

  Morgan Winn Maury People Sotheby's International Realty

  37 Sankaty Head Rd, Nantucket, MA 02554
• 

  

  /29

  $5,295,000

  • 6 Beds
  • 5.5 Baths
  • 4,956 Sq Ft

  75 Fairgrounds Rd, Nantucket, MA 02554

  Thoughtfully designed by J5 Development for modern living and seamless indoor-outdoor flow, 75 Fairgrounds Road will offer six bedrooms and five-and-a-half bathrooms across three finished levels. With an open-plan layout, multiple living areas, and sliding glass doors leading to the pool, deck, and cabana, this newly built home blends sophistication with laid-back island comfort. Ideal for

  Brian Sullivan Fisher Real Estate

  75 Fairgrounds Rd, Nantucket, MA 02554
• 

  /2

  $3,595,000

  $345K PRICE INCREASE

  • Land
  • 24,397 Sq Ft
  • $6,418,497 per Acre

  15 Nancy Ann Ln, Nantucket, MA 02554

  Commercial CTEC lot. Currently leased until September 30, 2027 with 2, 1 year extensions. Lease has excellent cash flow, making it ideal for an investor who wants to continue to lease it as raw land or recognizes the value for future development. Utilities; town water, (sewer is at 9-11 Nancy Ann) cable and electric are available at the street. The lot is 118x210, is flat and open and is

  Robert Young William Raveis Nantucket

  15 Nancy Ann Ln, Nantucket, MA 02554
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  /42

  $7,595,000

  $400K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,739 Sq Ft

  45 Starbuck Rd, Nantucket, MA 02554

  Coastal Elegance with Panoramic Views – 45 Starbuck Road, Nantucket (Madaket) Discover the best of Nantucket living in this beautifully designed 4-bedroom, 4.5-bathroom home located in the serene enclave of Madaket. Just a short stroll to the beach, this exceptional property offers breathtaking ocean and sunset views, setting the stage for unforgettable island experiences.Custom pool with

  Susan Shepherd Shepherd Real Estate

  45 Starbuck Rd, Nantucket, MA 02554
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  /69

  $11,500,000

  • 3 Beds
  • 1.5 Baths
  • 1,024 Sq Ft

  17 Massachusetts Ave, Nantucket, MA 02554

  A truly rare and prestigious opportunity to acquire direct waterfront property on Madaket Harbor. This exceptional offering includes a detached garage/party barn, and exclusive beach frontage—where the sand is yours to claim and the sunsets over Tuckernuck Island are nothing short of breathtaking. Set on the water’s edge, the custom three-bedroom, one and one half bath home presents endless

  Marybeth Gibson & Jessica Newman Maury People Sotheby's International Realty

  17 Massachusetts Ave, Nantucket, MA 02554
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  /2

  $3,300,000

  • Land
  • 1.85 Acres
  • $1,786,584 per Acre

  9 Millbrook Road (Portion), Nantucket, MA 02554

  This two-acre vacant lot is located in the Hummock Pond area, on the edge of Cisco. This area is highly sought after for its proximity to South Shore beaches, Hummock Pond Road bike path, Cisco Brewery, 167 Seafood, and Bartlett’s Farm. The property benefits from abutting and nearby conservation lands that will ensure open space and provide walking trails. This setting offers a rural feel and

  Greg McKechnie Great Point Properties

  9 Millbrook Road (Portion), Nantucket, MA 02554
• 

  

  /29

  $3,495,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,133 Sq Ft

  33 Bartlett Rd, Nantucket, MA 02554

  Centrally Located Nantucket Retreat with Backyard Oasis. Discover the perfect blend of custom and comfort in this newly renovated Nantucket home, ideally located with close proximity to Miacomet Golf Club, Surfside Beach and Town. Thoughtfully designed and currently configured as a five-bedroom, three-bath residence, this property offers exceptional versatility and a seamless indoor-outdoor

  John Arena William Raveis Nantucket

  33 Bartlett Rd, Nantucket, MA 02554
• 

  

  /50

  $4,595,000

  $400K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,788 Sq Ft

  27 Wigwam Rd, Nantucket, MA 02554

  Tucked near one of Nantucket’s most beloved South Shore beaches, this 5-bedroom, 4.5-bath upside-down beach house is a true coastal gem. Designed for both comfort and style, the home features soaring wood-beamed ceilings, an intricately inlaid compass rose in the hardwood floors, and a classic widow’s walk offering panoramic ocean views. With three distinct living areas—one on each level—plus a

  Chandra Miller Maury People Sotheby's International Realty

  27 Wigwam Rd, Nantucket, MA 02554
• 

  

  /21

  $3,495,000

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  3 Whitetail Cir, Nantucket, MA 02554

  Nestled on a high ridge in Tom Nevers, this beautifully crafted 3-bedroom, 2.5-bathroom home sits on 2.75 acres, offering breathtaking views across the Atlantic Ocean, Sankaty Lighthouse, and three of Nantucket's renowned golf courses—Sconset, Sankaty, and Skinners. Built by the legendary Chris Holland, the home has been meticulously maintained and serves as the perfect base for quintessential

  Brian Sullivan Fisher Real Estate

  3 Whitetail Cir, Nantucket, MA 02554
• 

  

  /29

  $5,950,000

  $800K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 4,460 Sq Ft

  86 Cliff Rd, Nantucket, MA 02554

  Delivered turnkey and impeccably appointed, 86 Cliff Road presents a rare opportunity to enjoy effortless luxury from day one, just in time for Nantucket’s most coveted seasons. An exceptional and recently built residence set within the highly sought-after Cliff neighborhood, the location offers easy access to The Westmoor Club, Tupancy Links, north shore beaches and Town. The five-bedroom home

  

  Jennifer Shalley Allen

  Fisher Real Estate

  86 Cliff Rd, Nantucket, MA 02554
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  /36

  $6,495,000

  $330K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,774 Sq Ft

  12 Willard St, Nantucket, MA 02554

  Welcome to 12 Willard Street, a stunning coastal retreat located in the heart of Brant Point, one of Nantucket’s most desirable neighborhoods. This beautifully renovated upside-down home offers a unique blend of contemporary elegance and classic island charm. With four spacious bedrooms and four and a half bathrooms, this home is perfect for families or groups. If you are seeking a luxurious and

  Morgan Winn Maury People Sotheby's International Realty

  12 Willard St, Nantucket, MA 02554
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  /76

  $4,950,000

  $50K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,542 Sq Ft

  318 Milestone Rd, Siasconset, MA 02564

  Sconset Retreat!Sited on a serene half-acre lot abutting the Sconset Land Trust, this bright and spacious, custom-designed contemporary home offers privacy, tranquility, and captivating sunset views—protected in perpetuity. Thoughtfully designed by S.M. Roethke and expertly built by Main Street Construction, the home seamlessly blends architectural elegance with modern functionality. Ideally

  Robert Sarkisian BHHS Island Properties Nantucket

  318 Milestone Rd, Siasconset, MA 02564
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  /5

  $34,500,000

  • 10 Beds
  • 9 Baths
  • 6,875 Sq Ft

  52 Monomoy Rd, Nantucket, MA 02554

  Commanding one of the most coveted harborfront locations on Nantucket, this extraordinary 1.25-acre estate offers truly unparalleled harborfront views and an unmatched coastal living experience. With sweeping, panoramic vistas stretching from Town across the harbor to Brant Point and Coatue, the property delivers a front-row seat to the island’s most iconic scenery. Enjoy sunsets over the water,

  Morgan Winn Maury People Sotheby's International Realty

  52 Monomoy Rd, Nantucket, MA 02554
• 

  

  /3

  $2,100,000

  $105K PRICE INCREASE

  • Land
  • 4,791 Sq Ft
  • $19,090,909 per Acre

  54 Union St, Nantucket, MA 02554

  Unique opportunity. Property located in Nantucket Town, one block from Francis Street beach and less than 1/2 mile from Main Street. Commercial neighborhood zoning with opportunity to build up to 40% of ground cover. Land is around the corner to announced town plans for Francis Street/Washington Street extension renovation and 14 Land Bank, Town-owned properties.

  Ty Costa William Raveis Nantucket

  54 Union St, Nantucket, MA 02554
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  /44

  $4,850,000

  $200K PRICE INCREASE

  • 4 Beds
  • 4.5 Baths
  • 2,352 Sq Ft

  8 Sconset Ave, Nantucket, MA 02554

  Ready for Summer 2026. Located in desirable 'Sconset village, this newly constructed Cape-style cottage has been thoughtfully expanded and fully renovated. Designed with an efficient use of space and the island lifestyle in mind, the four bedroom home with oversized garage and studio suite is ideal for coastal living and checks all the boxes. The flexible layout offers various options for

  Paul Drepanos Compass Massachusetts, LLC

  8 Sconset Ave, Nantucket, MA 02554
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  /78

  $10,950,000

  $3M PRICE DROP

  • 6 Beds
  • 8 Baths
  • 6,325 Sq Ft

  14 Correia Ln, Nantucket, MA 02554

  Luxury Estate in Surfside - Your Dream Home Awaits! Introducing a brand new exquisite construction in the heart of Surfside! This magnificent property offers a 5 bedroom main house, a 1 bedroom cottage, and an oversized garage, all nestled on a private 1 acre compound. The main house boasts five spacious bedrooms, each designed with luxurious finishes. The separate one- bedroom cottage provides

  Marybeth Gibson & Jessica Newman Maury People Sotheby's International Realty

  14 Correia Ln, Nantucket, MA 02554
• 

  

  /14

  $3,800,000

  $1M PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,920 Sq Ft

  35 W Chester St, Nantucket, MA 02554

  Three bedroom antique home and garage nestled between West Chester Street and Sunset Hill Road. Set on an oversized lot this property has almost 2,000 square feet of remaining ground cover. Near Lily Pond Park and the Oldest House, it offers a level of privacy that is rare for properties in the Residential Old Historic District. The house is located within the highest portion of the lot,

  Liz Finlay Great Point Properties

  35 W Chester St, Nantucket, MA 02554
• 

  

  /29

  $13,000,000

  • 4 Beds
  • 4.5 Baths
  • 3,159 Sq Ft

  40 Low Beach Rd, Nantucket, MA 02554

  Private, Protected Oceanfront Estate OpportunitySeize this rare chance to acquire one of the last Oceanfront properties in ’Sconset—an exceptional estate offering sweeping Atlantic views, Beach Access, and the freedom to reimagine or customize your dream coastal retreat. Set along one of Nantucket’s and ’Sconsets' most coveted coastal stretches, this private and protected property is offered

  Marybeth Gilmartin-Baugher Compass MA LLC

  40 Low Beach Rd, Nantucket, MA 02554
• 

  

  /27

  $2,395,000

  $1M PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,833 Sq Ft

  22 Sheep Pond Rd, Nantucket, MA 02554

  Turnkey! this gorgeous 4 bedroom and 3 bathroom property is surrounded by unobstructed ocean views and the beautiful moors of Madaket. Listen to the surf from every room. Walk just steps to the sandy, pristine beach, accessible only to residents of Sheep Pond Road. Wander down the beach to Millies for lunch, dinner or an ice cream, or stay home and enjoy cocktails and the celebrated Madaket

  Susan Shepherd Shepherd Real Estate

  22 Sheep Pond Rd, Nantucket, MA 02554

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