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27 Longwood Drive, Nantucket MA 02554

ActiveTom Nevers1 FamilySingle Family Residence

$3,975,000

$1,145 / sqft

Bedrooms

Bathrooms

4 + 1 half

Sq Ft

3,472

Lot

2.75 acres

Year Built

1990

Days on Market

178

Description

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.

Property Details

MLS #92560

StatusActive

Property Type1 Family

Sub TypeSingle Family Residence

NeighborhoodTom Nevers

MLS AreaTom Nevers

CityNantucket

StateMA

Zip02554

List Price$3,975,000

Original List Price$4,000,000

Price / Sq Ft$1,145

Bedrooms5

Full Baths4

Half Baths1

Total Rooms12

Living Area3,472 sqft

Lot Size2.75 acres

Year Built1990

Days on Market178

ZoningLUG3

FurnishedFurnished

Fireplaces1

PoolNo

GarageYes

SewerSeptic Tank

Water SourceWell

Second DwellingE/Sd

OwnerCosgrave

Parcel #74

Tax Map #76

Annual Tax$12,195

Assessed Value$2,480,300

Tax Year2025

HOA Fee$400 / Annually

On Market DateOct 27, 2025

First ListedMay 4, 2026

Last UpdatedMay 4, 2026

Latitude41.2565089

Longitude-70.0011015

Heating

GFHA

Parking

Yes

Exterior

DeckPorchC/Tennis

View

NonePasture

Utilities

Cbl

Flooring

Wood and Tile

Appliances

Stove: YesWasher: Yes 2

Interior Features

A,AC,Ins,Irr,OShFloor 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.

Foundation

Block

Lot Features

See document 1157 Title number 5041 Electric easementExpansive private yard

Additional MLS Details

SewerSeptic Tank

ZoningLUG3

Tax Year2025

FlooringWood and Tile

Garage YNtrue

LINK Psf1144.8732

Close Date2026-06-10

FurnishedFurnished

Owner NameCosgrave

AppliancesStove: Yes, Washer: Yes 2

Rooms Total12

Lot FeaturesSee document 1157 Title number 5041 Electric easement, Expansive private yard

Water SourceWell

On Market Date2025-10-27

Parcel Number74

Tax Map Number76

Pool Private YNfalse

Tax Annual Amount12195

Interior FeaturesA,AC,Ins,Irr,OSh, 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.

Tax Assessed Value2480300

Fireplace Features1

Foundation DetailsBlock

Original List Price4000000

LINK Listing Dwell2E/Sd

Price Change Timestamp2026-04-06T10:45:17.113Z

Original Entry Timestamp2025-08-25T09:47:39.853Z

Listing Agent

Debbie Willett

Great Point Properties

Price History

Date	Event	Price	Change
May 4, 2026	Listed	$3,975,000

Sales History

Date	Sale Price	List Price	Buyer	MLS #
May 14, 2007	$2,300,000	$2,250,000	Patricia Cosgrave	65991

Tax History

Year	Tax Amount	Assessed Value	Land	Improvements
2025	$12,195	$2,480,300	—	—

Market Context

Tom Nevers Avg

$5,347,222

Tom Nevers Median

$4,995,000

Island Avg

$6,064,676

Island Median

$4,299,000

Property Context

Wetlands NearbyNo

Source: MassGIS / FEMA NFHL. For informational purposes only — verify with Town of Nantucket.

MLS Listing #92560 — Data as of 2026-05-04