27 Longwood Drive Nantucket, MA 02554

Tom Nevers

Overview
Property Details
Video / 3D Tour
Location

Contact Agent

$4,000,000

Asking Price

Bedrooms

4.1

Bathrooms

3,472

Square Footage

Welcome to 27 Longwood Drive, Nantucket — a private 2.75-acre estate offering refined coastal living and timeless Nantucket charm. This spacious upside-down home features five bedrooms, three full bathrooms, and one half bathroom, perfectly designed for comfort, entertaining, and relaxation. Step into the inviting foyer with its dramatic curved staircase, leading to a stunning second-floor living area. The open-concept layout includes a cathedral-ceiling great room, custom fireplace, and a large dining space ideal for gatherings. The gourmet kitchen boasts distant views of Sankaty Light, bringing the island’s natural beauty right into your home. From the second-floor deck, enjoy serene mornings with coffee or peaceful evenings under the stars—an unmatched combination of privacy and tranquility. The lower level offers two covered porches, perfect for year-round outdoor entertaining. A beautifully designed carriage house complements the main residence, featuring an oversized two-bay garage, one bedroom, and one bathroom—ideal for guests or extended family seeking privacy. This exceptional Nantucket property at 27 Longwood Drive also allows for an additional 2,200 square feet of ground cover, offering ample opportunity to expand or customize your dream island retreat.

First Floor

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.

Second Floor

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.

Total Rooms 12
Total Beds 5
Full Baths 4
Half Baths 1

Lot Size 2.75 acres
Year Built 1990
Second Dwelling Yes

Zoning LUG3

Listed on October 27, 2025 by Great Point Properties

27 Longwood Drive - Sales History

Selling date: 5/14/2007

Selling price: $2,300,000

Location

What we like about Tom Nevers

Tom Nevers beach is a great swimming destination that features a nearby playground and a large open field. Tom Nevers is also home to beautiful south shore beaches and is a favorite spot to fish for striped bass and bluefish in the summertime.

Learn more