27 Longwood Drive • $3,750,000 Active Under Contract

Tom Nevers, Nantucket, MA 02554

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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.

Floor 1: 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.

Floor 2: 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.

Parking: Yes

Listed by Great Point Properties

Virtual Tour
27 Longwood Drive Location
Property Code: #92560
Bedrooms:
5 beds
Bathrooms:
4 and 1 half
Lot:
119,790 sq ft
Year Built:
1990
Heating Type:
GFHA
Listed:
260 ago
Assessed Value:
$3,718,800

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Property Information for 27 Longwood Drive
Property Summary

Type: 1 Family

Rooms: 12

Year Built: 1990

Remodeled:

Water View:

Other View: Pasture

Zoning: LUG3

Lot Size(SF): 3472

Furnished: Furnished

2nd Dwelling: E/Sd

Water: Well

Sewer: Septic Tank

Lot Size(A): 2.75

Beds/Baths: 5/4

Wtr Frontage:

Total SqFt(GLA): 119790

Amenities

First Floor Bedrooms: 3

Heating: GFHA

Fireplaces: 1

Floors: Wood and Tile

Yard: Expansive private yard

Parking: Yes

Foundation: Block

Lead Paint:

Recreation and Outdoor Spaces: Deck, Porch, C/Tennis

Amenities:

Taxes and Fees

Building Assessment: 2480300

Land Assessment: 1238500

Total Assessment: 3718800

Tax Year: 2025

Property History for 27 Longwood Drive
Jul 24, 2026
Active Under Contract
27 Longwood Drive :: Tom Nevers
$3,750,000
1 Family
260 Days on Market
Listed by: Great Point Properties
May 14, 2007
Closed
27 Longwood Drive - Tom Nevers
Listed Price
$2,250,000
Sold Price
$2,300,000
1 Family
0 Days on Market
Listed by: Maury People Sotheby's International Realty
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