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      • Madaket
      • Madequecham
      • Miacomet
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      • Monomoy
      • Muskeget
      • Nashaquisset
      • Naushop
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      • Quaise
      • Quidnet
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(508) 228-6999

27 Longwood Drive, Nantucket, MA 02554

$3,750,000

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  • 5 BedBeds
  • 4.5 BathBaths
  • 3,472 SqftSqft
  • TypeSingle Family
  • Active
  • Listing # 92560
-1 More Schedule

Property Description 27 Longwood Drive, 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 large dining area, and a kitchen with a distant view of Sankaty Light. The 2nd-floor deck, located off the living room, offers an uncompromising blend of comfort and seclusion, perfect for enjoying morning coffee or stargazing. Downstairs, you'll find two additional covered porches for entertaining and enjoying all year round. The carriage house, featuring an oversized two-bay garage, one bedroom, and one bathroom, is ideal for a large family and provides privacy for both you and your guests.

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Entering the home through the covered porch, the generous foyer features custom design elements and includes three bedrooms, two full bathrooms, a laundry closet, and a workshop/storage area. Another covered porch off the foyer offers ample room for entertaining and enjoying the spacious yard and outdoor shower.

Light-filled open living space featuring a white kitchen with counter stools, dining area with seating for 10, living room, and powder room. The living room features a cathedral ceiling with natural wood beams, a custom fireplace with bookcases, and an architectural Palladian window with a cushioned bench seat. Access to the second-floor deck off the living room. The master en-suite bedroom with dressing area completes the second floor.

Area

Tom Nevers is located at the South East end of the island between Madequcham and Sconset. This area is a favorite amongst seasonal and year-round visitors alike for it's seclusion, laid back atmosphere and being away from it all. Tom Nevers East features larger lots in varying elevations to take advantage of views towards the ocean and moors. Tom Nevers West features more densely populate lots, although much larger in comparison to in Town lots, in cute neighborhoods with streets named after Boston streets. Towards the end of Tom Nevers Road you will find larger lots and ocean front properties. A big draw of this area is the open space of land owned by Nantucket Conservation Foundation.

  • 4.6 miles to Town
  • 2.9 miles to Sconset
  • Tom Nevers beach is a surf beach on the Atlantic Ocean with generally little to no crowds.
  • Tom Nevers Field offers recreational spaces for all ages including baseball fields and a playground. Many of the island adult league softball teams play here in the spring.
  • The Nantucket Conservation Foundation owns 2,150 acres of land between Madequecham and Tom Nevers containing unique geological and natural communities. There are several trails throughout for you to enjoy, but be sure to check for ticks upon return home as the deer population in this area is large.
  • Just a short trek across Milestone Road you will find the NCF Milestone Cranberry Bogs. The Fall Harvest Festival is held here annually and it is a great place for biking, walking or running.
  • Also across Milestone Road you will find entrances to the NCF Moors properties for even more exploring.

community

Property Details

  • Property Type: Single Family
  • List Date: 10/27/2025
  • Year Built: 1990
  • Area: Tom Nevers
  • Zoning: LUG3
  • Beds: 5
  • Full Bath: 4
  • Half Bath: 1
  • Total Baths: 5
  • Annual Taxes: $12,195.00
  • Tax Year: 2025
  • Water Frontage: No
  • Water Views: No
  • Other Views: None, Pasture
  • Water: Well
  • Sewer: Septic Tank

Amenities

Interior FeaturesInterior Features
  • Furnished: Furnished
  • Heat: GFHA
  • Fireplaces: 1
Exterior FeaturesExterior Features
  • Private Pool: No
  • Community Pool: No
  • Private Tennis: No
  • Community Tennis: No
  • Hot Tub: No
  • Parking: Yes
Other StructuresOther Structures

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    This calculator is provided for informational purposes only by Burrow Services, Inc. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

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