27 Longwood Drive • $3,750,000

Tom Nevers, Nantucket, MA 02554

Search

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:
248 ago
Assessed Value:
$3,718,800

Contact Agent

x
Name is required
Valid E-Mail is required
Phone is required

I agree to be conntacted by J Pepper Frazier Co via call, email and text. To opt out, you can reply "stop" any time or click unsubscribe link in the emails.

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
Jun 29, 2026
Active
27 Longwood Drive :: Tom Nevers
$3,750,000
1 Family
248 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
Similar Houses for Sale
18 Honeysuckle Drive Sandpiper
$3,725,000
18 Honeysuckle Drive Sandpiper
4 Beds
4 Baths
DOM: 88
4 Fawn Lane Mid Island
$3,699,000
4 Fawn Lane Mid Island
5 Beds
5 Baths
DOM: 104
8 East Dover Street Town
$3,695,000
8 East Dover Street Town
4 Beds
3 Baths
DOM: 29
24 Washaman Avenue Nashaquisset
$3,595,000
24 Washaman Avenue Nashaquisset
3 Beds
3 Baths
DOM: 27
3 Wigwam Road Madequecham
$3,595,000
3 Wigwam Road Madequecham
4 Beds
3 Baths
DOM: 4
15 Nancy Ann Lane Mid Island
$3,595,000
15 Nancy Ann Lane Mid Island
0 Beds
0 Baths
DOM: 357
12 Myles Standish Street Surfside
$3,500,000
12 Myles Standish... Surfside
Beds
Baths
DOM: 283
3 Cottage Court Town
$3,495,000
3 Cottage Court Town
3 Beds
3 Baths
DOM: 92
33 Bartlett Road South of Town
$3,495,000
33 Bartlett Road South of Town
3 Beds
3 Baths
DOM: 388
3 Whitetail Circle Tom Nevers
$3,495,000
3 Whitetail Circle Tom Nevers
3 Beds
2 Baths
DOM: 296
4 Flintlock Road Tom Nevers
$3,775,000
4 Flintlock Road Tom Nevers
5 Beds
4 Baths
DOM: 51
6 Maple Lane Mid Island
$3,800,000
6 Maple Lane Mid Island
Beds
Baths
DOM: 100
35 West Chester Street Town
$3,800,000
35 West Chester... Town
3 Beds
1 Baths
DOM: 412
2 Fawn Lane Mid Island
$3,800,000
2 Fawn Lane Mid Island
5 Beds
5 Baths
DOM: 73
9 Priscilla Lane West of Town
$3,990,000
9 Priscilla Lane West of Town
3 Beds
2 Baths
DOM: 23
21 Equator Drive South of Town
$3,995,000
21 Equator Drive South of Town
5 Beds
4 Baths
DOM: 50
37 Main Street Sconset
$3,995,000
37 Main Street Sconset
Beds
Baths
DOM: 24
1 East Lincoln Avenue Brant Point
$3,995,000
1 East Lincoln... Brant Point
4 Beds
3 Baths
DOM: 43
2 Lily Street Sconset
$3,999,999
2 Lily Street Sconset
6 Beds
3 Baths
DOM: 6
22 Tashama Lane South of Town
$4,095,000
22 Tashama Lane South of Town
5 Beds
4 Baths
DOM: 39
Back to top