Homes for Sale near Montessori Children's House of Nantucket

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  /69

  $2,995,000

  • 4 Beds
  • 2 Baths
  • 1,941 Sq Ft

  36 Sheep Pond Rd, Nantucket, MA 02554

  Sweeping ocean views, spectacular sunsets and authentic Nantucket charm located at 36 Sheep Pond Road. This beach retreat, abutting conservation land, offers four bedrooms in the main house and a separate finished studio with a full bath and kitchenette. Two additional structures allow for extra storage and studio space. Sited on a two acre lot with expansion potential-seven bedroom septic in

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 290-8742

  36 Sheep Pond Rd, Nantucket, MA 02554
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  /6

  $2,395,000

  • 2 Beds
  • 2 Baths
  • 884 Sq Ft

  2A Forest Ave Unit 5, Nantucket, MA 02554

  This unique property offers exceptional versatility and functionality, featuring an oversized three-bay garage is ideal for vehicle storage. Above the garage, you'll find a spacious 2-bedroom, 2-bathroom apartment with a well-designed layout, perfect for comfortable living. The full basement provides ample storage space and offers potential for future finish-out as additional living area, office

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 422-5291

  2A Forest Ave Unit 5, Nantucket, MA 02554
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  /6

  $2,395,000

  • 2 Beds
  • 2 Baths
  • 884 Sq Ft

  2B Forest Ave Unit 6, Nantucket, MA 02554

  This unique property offers exceptional versatility and functionality, featuring an oversized three-bay garage is ideal for vehicle storage. Above the garage, you'll find a spacious 2-bedroom, 2-bathroom apartment with a well-designed layout, perfect for comfortable living. The full basement provides ample storage space and offers potential for future finish-out as additional living area, office

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 332-9088

  2B Forest Ave Unit 6, Nantucket, MA 02554
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  /36

  $6,825,000

  • 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

  (508) 409-5059

  12 Willard St, Nantucket, MA 02554
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  /4

  $1,395,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  2A Forest Ave Unit 1, Nantucket, MA 02554

  Experience the privacy of a free-standing condo combined with the ease of low-maintenance living. Built with high-quality stick construction and accented with cedar trim, this charming cottage showcases timeless craftsmanship. Enjoy the beauty of white cedar siding, a red cedar roof, and Andersen windows that offer both comfort and durability. With dedicated parking for two and a welcoming front

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 988-8158

  2A Forest Ave Unit 1, Nantucket, MA 02554
• 

  

  /4

  $1,395,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  2B Forest Ave Unit 2, Nantucket, MA 02554

  Experience the privacy of a free-standing condo combined with the ease of low-maintenance living. Built with high-quality stick construction and accented with cedar trim, this charming cottage showcases timeless craftsmanship. Enjoy the beauty of white cedar siding, a red cedar roof, and Andersen windows that offer both comfort and durability. With dedicated parking for two and a welcoming front

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 419-9322

  2B Forest Ave Unit 2, Nantucket, MA 02554
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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

  (508) 731-3567

  52 Monomoy Rd, Nantucket, MA 02554
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  /48

  $11,995,000

  • 5 Beds
  • 4.5 Baths
  • 3,344 Sq Ft

  20 N Pasture Ln, Nantucket, MA 02554

  Welcome to 20 North Pasture Lane, a stunningly reimagined estate nestled in the serene Polpis area of Nantucket. Set on 2.75 acres bordering conservation land, this beautifully renovated home offers views of Polpis Harbor and the quiet privacy of one of the island’s most peaceful neighborhoods. In 2024, the property underwent a full, top-to-bottom renovation, enhancing every inch with thoughtful

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 545-9673

  20 N Pasture Ln, Nantucket, MA 02554
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  /56

  $6,995,000

  • 5 Beds
  • 4 Baths
  • 2,388 Sq Ft

  56 Meadow View Dr, Nantucket, MA 02554

  This exquisite hidden gem, surrounded by breathtaking landscaping, offers a serene retreat for your Nantucket dream home. Ideally situated just 1.5 miles from the ferry docks and a half-mile from Nantucket Town's Historic District in the charming Hussey Farm neighborhood, this location provides effortless access to the island’s renowned restaurants, boutiques, and beaches—while ensuring complete

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 593-9769

  56 Meadow View Dr, Nantucket, MA 02554
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  /47

  $17,750,000

  • 6 Beds
  • 5.5 Baths
  • 4,299 Sq Ft

  113 Eel Point Rd, Nantucket, MA 02554

  Welcome to your dream beachfront home! This stunning property features an expansive open-concept living space that seamlessly integrates the kitchen, dining, and living areas, perfect for both entertaining and relaxing. Elegant French doors open to a generous patio with direct access to a private walkway leading to the beach, offering unparalleled views and immediate access to the oceanfront. The

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 719-9965

  113 Eel Point Rd, Nantucket, MA 02554
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  /59

  $5,800,000 Open Thu 11AM - 1AM

  • 8 Beds
  • 10 Baths
  • 4,761 Sq Ft

  12 & 13 Shimmo Pond Rd, Nantucket, MA 02554

  SHIMMO: Charming 4-Bedroom Home with 2-Bedroom Cottage on expansive grounds in the coveted Shimmo locale.Shimmo Pond Road, where sandy paths wind beneath leafy canopies and Nantucket Harbor beckons in the distance- this exceptional property captures the timeless charm of a countryside residence. Set on an oversized and private parcel, the beautifully proportioned 4-bedroom main house is

  Sheila Carroll Maury People Sotheby's International Realty

  12 & 13 Shimmo Pond Rd, Nantucket, MA 02554
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  /36

  $7,200,000

  • 5 Beds
  • 8 Baths
  • 4,352 Sq Ft

  2 Old Mill Ct, Nantucket, MA 02554

  Experience the best of summer living on Nantucket with this custom-built five-bedroom home, completely turnkey, close to Town, and available for immediate occupancy. Thoughtfully designed and offered fully furnished, in part by Nantucket Looms, this home features five bedrooms and over 4,300 square feet of living space on three levels. Featuring open concept living/dining/kitchen, as well as a

  Ethan Ulmer Great Point Properties

  2 Old Mill Ct, Nantucket, MA 02554
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  /22

  $1,495,000

  • 1 Bed
  • 1.5 Baths
  • 612 Sq Ft

  14 Still Dock St Unit E, Nantucket, MA 02554

  Tucked along Still Dock in downtown Nantucket, this beautifully renovated 1-bedroom, 1.5-bath unit offers an easy, elegant island lifestyle. Every detail has been thoughtfully considered, from the marble finishes to the custom millwork. Grab a coffee at Provisions, people watch on the docks, or bike to one of the many nearby beaches. Dining & shopping in every direction providing a fabulous

  Chandra Miller Maury People Sotheby's International Realty

  14 Still Dock St Unit E, Nantucket, MA 02554
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  /62

  $6,795,000

  • 5 Beds
  • 5.5 Baths
  • 3,937 Sq Ft

  55 Orange St, Nantucket, MA 02554

  A piece of history tailored for today's living. This exquisitely restored 1824 four-bay home, built by Captain John C. Gardner, invites us to appreciate an antique gem. A rich texture of history blends seamlessly with elevated updates and modern amenities across four finished levels. It's a joy to experience a classic Nantucket house with refined interiors and two-car off-street parking. Of

  Carolyn Durand Lee Real Estate

  55 Orange St, Nantucket, MA 02554
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  /42

  $7,995,000

  • 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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  /62

  $5,295,000

  • 4 Beds
  • 6 Baths
  • 3,298 Sq Ft

  3 Pinkham Cir, Nantucket, MA 02554

  Nestled at the end of a tranquil cul-de-sac in Hussey Farm, this exceptional property offers a rare combination of privacy, sanctuary, and thoughtful design. Set on a beautifully landscaped acre, the rewards at this property must be seen to appreciate. The mature plantings and curated outdoor spaces create a special retreat. Completely rebuilt in 2012, the main house flows seamlessly with great

  Carolyn Durand Lee Real Estate

  3 Pinkham Cir, Nantucket, MA 02554
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  /27

  $6,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,742 Sq Ft

  2 Shore Rd, Nantucket, MA 02554

  A truly rare opportunity to own a harbor-view property with unmatched development potential — 2 Shore Rd lot is 11,484 ft, 50% ground cover by right for 5 years from purchase (grandfathered from CN conversion). That equates to 5,742 sq ft of buildable ground cover — a scope nearly impossible to find this close to Town, with direct harbor views.The property currently includes:Main

  Ty Costa William Raveis Nantucket

  2 Shore Rd, Nantucket, MA 02554
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  /64

  $6,195,000

  • 5 Beds
  • 4.5 Baths
  • 4,861 Sq Ft

  5 Upper Tawpawshaw Rd, Nantucket, MA 02554

  Welcome to "Edgemoor", a private island retreat nestled on a quiet cul de sac in Nantucket. This beautifully appointed 5 bedroom residence combines timeless charm with modern amenities, set on a generous lot abutting hundreds of acres of protected conservation land with direct access to walking paths from your own backyard. Natural light pours in the window-filled, designer decorated, living

  Daniel Barber Maury People Sotheby's International Realty

  5 Upper Tawpawshaw Rd, Nantucket, MA 02554
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  /40

  $5,195,000

  • 4 Beds
  • 4 Baths

  27 N Liberty St, Nantucket, MA 02554

  A masterful 2024 restoration by renowned Kolb Architects has transformed this 1790 gem into a sophisticated in-town retreat, blending historic charm with modern luxury. Perched above the Lily Pond, the home offers sweeping pastoral views from an expansive back deck—some of the most serene and sought-after vistas in Nantucket’s Historic District.This four-bedroom, four-and-a-half-bath

  Bernadette Meyer Maury People Sotheby's International Realty

  27 N Liberty St, Nantucket, MA 02554
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  /3

  $5,995,000

  • 15 Beds
  • 14.5 Baths
  • 5,643 Sq Ft

  27 Fair St, Nantucket, MA 02554

  Sitting high on Fair Street on a oversized rolling lot, 27 Fair Street was originally built as a single family home and then later converted to an inn with an annex building at the rear of the lot. There are plans to reconfigure the existing inn into a six key inn and build three, free-standing two-story suites where the annex building currently exists. Or, convert back to a single family home

  Dalton Frazier J Pepper Frazier Co.

  27 Fair St, Nantucket, MA 02554
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  /99

  $5,200,000

  • 4 Beds
  • 4 Baths
  • 2,618 Sq Ft

  10 New Ln, Nantucket, MA 02554

  "Winds Aloft" 5 Bedrooms | 4 Baths | Private Pool | Two-Car Garage with Guest Suite. Tucked away on a peaceful and generously sized 20,000 sq ft lot, "Winds Aloft" is an exceptional Nantucket residence that blends timeless design with effortless coastal living.The sun-drenched, open-concept main house features three bedrooms plus a flexible den space, and gracious

  Christine Carpenter William Raveis Nantucket

  10 New Ln, Nantucket, MA 02554
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  /50

  $4,995,000

  • 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
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  /39

  $1,595,000

  • 2 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

  2 Yawkey Way Unit 2, Nantucket, MA 02554

  Spacious and well built duplex by local high-end contractor with 30 years experience building on the island. The left half has three floors of finished space. Only the highest quality materials were used in construction, with reclaimed oak floors, custom-built cabinetry, built-in entertainment center and ample storage throughout. A large deck in the rear offers private outdoor entertainment

  John F. Trudel III Maury People Sotheby's International Realty

  2 Yawkey Way Unit 2, Nantucket, MA 02554
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  /67

  $5,195,000

  • 4 Beds
  • 4 Baths
  • 3,070 Sq Ft

  25C Pine St, Nantucket, MA 02554

  Situated on historic Pine Street, just off the cobblestones of Main, offering the opportunity to live in the heart of downtown Nantucket. This quiet, one-way street is just moments from award-winning restaurants, boutique shopping, and the ferries, placing the best of Town just moments from your door. Its location on one of Nantucket’s most iconic streets makes it a standout opportunity for those

  Laura Belair Great Point Properties

  25C Pine St, Nantucket, MA 02554
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  /38

  $5,995,000

  • 7 Beds
  • 4 Baths
  • 3,976 Sq Ft

  13 Cliff Rd, Nantucket, MA 02554

  This early 20th-century home, dubbed "the Fluke" due to its whale-tail footprint, has been loved and enjoyed as a year-round and summer retreat by multiple generations of the same family for over fifty years. It is beautifully nestled on a large lot amongst grand homes on coveted Cliff Road. With surprising spaces for entertaining and for quiet retreat, the property enjoys an elevated perch over

  Bill Liddle Great Point Properties

  13 Cliff Rd, Nantucket, MA 02554
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  /52

  $4,995,000

  • 4 Beds
  • 4 Baths
  • 2,120 Sq Ft

  198 Hummock Pond Rd, Nantucket, MA 02554

  Cisco Charmer on 2 Private Acres...Nestled in the heart of Nantucket’s highly coveted Cisco area, this beautifully maintained 3-bedroom, 3-bathroom home offers the perfect blend of farmhouse charm and pastoral tranquility. Set on 2 acres, this private oasis has direct access to a scenic walking trail that leads to Cisco’s famed beaches. The main house features sun-drenched living spaces with

  Patty Tasch William Raveis Nantucket

  198 Hummock Pond Rd, Nantucket, MA 02554
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  /11

  $5,950,000

  • 5 Beds
  • 5.5 Baths
  • 3,556 Sq Ft

  4 Sunset Hill Ln, Nantucket, MA 02554

  Four sunset hill is a home that breathes history tucked into the heart of Nantucket town and perched on a high point. This home tells the story of a full scale renovation where heritage meet soft, sculptural finishes, and history holds hands with modern ease. Restored with a fabulous floor plan incorporating an open living concept, 5 bedrooms, 5 ensuite baths, and several living areas to enjoy

  Chandra Miller Maury People Sotheby's International Realty

  4 Sunset Hill Ln, Nantucket, MA 02554
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  /20

  $1,550,000

  • 2 Beds
  • 3.5 Baths
  • 1,995 Sq Ft

  3 Yawkey Way Unit 2 (Right side), Nantucket, MA 02554

  Step into this stunning, sun-drenched home offering four beautifully finished floors of living space. Featuring reclaimed oak floors and custom-built cabinetry, this home combines warmth with a thoughtful design.Enjoy a built-in entertainment area perfect for cozy nights or hosting guests, a convenient laundry closet, and generous storage options. The private deck and landscaped yard

  Angel Frazier Atlantic East Nantucket Real Estate

  3 Yawkey Way Unit 2 (Right side), Nantucket, MA 02554
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  /67

  $4,940,000

  • 5 Beds
  • 6 Baths
  • 4,871 Sq Ft

  15 Skyline Dr, Nantucket, MA 02554

  Enjoy tremendous privacy and close proximity to south shore beaches in this 5 bedroom, Surfside Estate. At 3.23 acres it is one of the largest residential properties currently available. A serpentine driveway winds through the pines to this handsome professionally landscaped home. You enter into a spacious living room with fire place, soaring ceilings open to the dining area and new kitchen. A

  Cynthia Lenhart William Raveis Nantucket

  15 Skyline Dr, Nantucket, MA 02554
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  /32

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 3,045 Sq Ft

  13 Derrymore Rd, Nantucket, MA 02554

  Ideally located in the sought-after Cliff neighborhood, this turnkey five-bedroom home is just moments from North Shore beaches, The Westmoor Club, Something Natural, and downtown Nantucket. Offered fully furnished, the property features three levels of living space, a first-floor primary suite, two inviting living areas, and ensuite guest bedrooms—making it the perfect island retreat.

  Jennifer Shalley Allen Fisher Real Estate

  13 Derrymore Rd, Nantucket, MA 02554
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  /31

  $4,995,000

  • 4 Beds
  • 3 Baths
  • 2,260 Sq Ft

  15 Meader St Unit A and D, Nantucket, MA 02554

  2 charming and sophisticated cottages (4 bedrooms total) side by side with harbor views that provide a wonderful opportunity for a variety of uses. Ideal as a family compound for multi-generations or use one and rent the other. Located in the heart of Nantucket's historic village, one block from the harborfront with its sandy beach and a moment's walk to Main Street. Featuring off-street parking,

  Jenny Paradis & Roberta White Maury People Sotheby's International Realty

  15 Meader St Unit A and D, Nantucket, MA 02554
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  $5,590,000 Open Thu 10:30AM - 12PM

  • 6 Beds
  • 4.5 Baths
  • 4,000 Sq Ft

  22 Vestal St, Nantucket, MA 02554

  This newly constructed home at 22 Vestal Street is perfectly positioned in town proper, just a short distance from historic downtown Nantucket and the island’s pristine beaches. Built by one of Nantucket’s premier builders, this stunning residence spans over 4,000 square feet and features six bedrooms and four-and-a-half baths. Designed and styled by LTW Design, the home offers a sophisticated

  Chris Kling J Pepper Frazier Co.

  22 Vestal St, Nantucket, MA 02554
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  /79

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 4,600 Sq Ft

  6 Gingy Ln, Nantucket, MA 02554

  Custom built 5 bedroom, 5.5 bathroom home on highly sought after Gingy Lane moments to Town and north shore beaches offers the perfect blend of modern luxury and timeless island charm. The light filled open plan naturally flows to side deck and patio. Versatile layout that offers the lower level as a separate "apartment" or an extension of the house. Gorgeous built-ins and millwork throughout.

  Josh Lothian William Raveis Nantucket

  6 Gingy Ln, Nantucket, MA 02554
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  /57

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 4,600 Sq Ft

  6 Gingy Ln, Nantucket, MA 02554

  Custom built 5 bedroom, 5.5 bathroom home on highly sought after Gingy Lane moments to Town and north shore beaches offers the perfect blend of modern luxury and timeless island charm. The light filled open plan naturally flows to side deck and patio. Versatile layout that offers the lower level as a separate "apartment" or an extension of the house. Gorgeous built-ins and millwork throughout.

  Dalton Frazier J Pepper Frazier Co.

  6 Gingy Ln, Nantucket, MA 02554
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  /14

  $5,495,000

  • 5 Beds
  • 4 Baths
  • 3,840 Sq Ft

  31 Western Ave, Nantucket, MA 02554

  Opportunity abounds to convert the stunning property into a private residence. Originally U.S. Life-Saving Station, then Star of the Sea Youth Hostel and now it awaits its new steward. Premium location on an oversized lot with unobstructed ocean views abutting Land Bank land and stairs to the beach across the street. Opportunity for an 81L sub-division. Approved 16 room septic design. Rare

  Dalton Frazier J Pepper Frazier Co.

  31 Western Ave, Nantucket, MA 02554
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  /16

  $2,700,000

  • 6 Beds
  • 6 Baths
  • 4,644 Sq Ft

  20 Pine Grove Ln, Nantucket, MA 02554

  Great opportunity for investment or employee housing all new shingles side and roof and new windows. gas heat all metered separate both electric and gas. This is a side by side duplex. Both sides have a first floor bedroom, kitchen, dining and living room.full bath/laundry room. Second floor has two bedrooms and a hall full bath. Both duplexes have separate full lower level living areas and

  Robert F Egan J Pepper Frazier Co.

  20 Pine Grove Ln, Nantucket, MA 02554
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  /10

  $4,400,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  3 & 3B Wyers Way, Nantucket, MA 02554

  Two adjacent lots with building permits in hand. The site has an existing cottage and separate garage and is located down a private lane, with proximity to Town and the Cliff area. The site has versatility and can be developed as a single home site with ample space, or as two home sites. The two-lot scenario benefits from Botticelli & Pohl-approved house plans, including pools. This offering

  Greg McKechnie Great Point Properties

  3 & 3B Wyers Way, Nantucket, MA 02554
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  /99

  $7,895,000

  • 4 Beds
  • 3 Baths
  • 2,456 Sq Ft

  1 Little Neck Way Unit 1, Nantucket, MA 02554

  Quintessential Nantucket Cottage on Madaket Harbor.Escape to the edge of the island in this classic 4-bedroom, 3-bath cottage perched directly on the tranquil shores of Madaket Harbor. Offering panoramic, unobstructed water views and direct access to a sandy beach, this is a rare coastal retreat where you can savor the very best of Nantucket's natural beauty and maritime lifestyle.An

  Gloria Grimshaw William Raveis Nantucket

  1 Little Neck Way Unit 1, Nantucket, MA 02554
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  /25

  $995,000

  • 2 Beds
  • 1 Bath
  • 955 Sq Ft

  16A Boynton Ln Unit A, Nantucket, MA 02554

  This well-designed 2-bedroom, 1-bath condo offers comfortable living across three levels, conveniently situated near all mid-island amenities and less than two miles from Surfside Beach.

  Liz Finlay Great Point Properties

  16A Boynton Ln Unit A, Nantucket, MA 02554
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  /29

  $1,995,000

  • 3 Beds
  • 4 Baths
  • 2,406 Sq Ft

  11 1st Way, Nantucket, MA 02554

  This welcoming Colonial-style home, circa 1997, is nestled on a spacious 1.8± acre lot, offering exceptional privacy and sweeping views of the surrounding natural landscape. A rare find, the property offers the best of both worlds: peaceful seclusion and easy access to town, schools, shopping, and beaches.The home features a traditional yet thoughtfully updated layout with three

  Elizabeth Almodobar Berkshire Hathaway HomeServices Island Properties Nantucket

  11 1st Way, Nantucket, MA 02554

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