$4,000,000

27 Longwood Dr Nantucket, MA 02554

Estimated payment $21,820/month

Total Views 9,678
5 Beds
4.5 Baths
3,472 Sq Ft
$1,152 Price per Sq Ft

Highlights

  • 2.75 Acre Lot
  • Deck
  • Furnished
  • Pasture Views
  • Cathedral Ceiling
  • Tennis Courts

About This Home

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.

Listing Agent

Debbie Willett

Great Point Properties Listed on: 10/27/2025

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $12,195

Year Built

  • Built in 1990

Lot Details

  • 2.75 Acre Lot
  • Property is zoned LUG3

HOA Fees

  • $33 Monthly HOA Fees

Parking

  • Garage

Home Design

  • Block Foundation

Interior Spaces

  • 3,472 Sq Ft Home
  • Furnished
  • Cathedral Ceiling
  • Fireplace
  • Pasture Views

Bedrooms and Bathrooms

  • 5 Bedrooms | 3 Main Level Bedrooms

Outdoor Features

  • Deck
  • Porch

Utilities

  • Well
  • Septic Tank
  • Cable TV Available

Listing and Financial Details

  • Tax Lot 866
  • Assessor Parcel Number 74

Community Details

Overview

  • Association fees include $300 per year for tennis court use

Recreation

  • Tennis Courts

Home Details

Home Type

Single Family

Est. Annual Taxes

$12,195

Year Built

Built in 1990

Lot Details

0

HOA Fees

$33 per month

Listing Details

  • Property Sub Type: Single Family Residence
  • Prop. Type: Residential
  • Road Frontage Type: None
  • Lot Size Acres: 2.75
  • Garage Yn: Yes
  • Year Built: 1990
  • Special Features: None

Interior Features

  • Furnished: Furnished
  • Possible Use: 5004-56
  • Appliances: Stove: Yes, Washer: Yes 2
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Total Bedrooms: 5
  • Fireplace Features: 1
  • Fireplace: No
  • Flooring: Wood and Tile
  • Interior Amenities: A,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.
  • Main Level Bedrooms: 3

Exterior Features

  • Lot Features: See document 1157 Title number 5041 Electric easement, Expansive private yard
  • Pool Private: No
  • View: None, Pasture
  • Exterior Features: Deck, Porch, C/Tennis
  • Foundation Details: Block

Garage/Parking

  • Parking Features: Yes

Utilities

  • Heating: GFHA
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well

Condo/Co-op/Association

  • Association Fee: 400
  • Association Fee Frequency: Annually

Fee Information

  • Association Fee Includes: $300 per year for tennis court use

Lot Info

  • Lot Size Sq Ft: 119790
  • Parcel #: 74
  • Zoning: LUG3

Green Features

Multi Family

Tax Info

  • Tax Annual Amount: 12195
  • Tax Lot: 866
  • Tax Map Number: 76
  • Tax Year: 2025

Map

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $12,198 $3,718,800 $1,238,500 $2,480,300
2024 $11,629 $3,715,300 $1,238,500 $2,476,800
2023 $9,981 $3,109,300 $1,180,000 $1,929,300
2022 $9,632 $2,575,400 $1,032,500 $1,542,900
2021 $9,443 $2,601,400 $1,032,500 $1,568,900
2020 $8,495 $2,462,200 $835,800 $1,626,400
2019 $8,273 $2,462,200 $835,800 $1,626,400
2018 $8,286 $2,347,300 $835,800 $1,511,500
2017 $7,735 $2,281,800 $799,000 $1,482,800
2016 $7,085 $2,108,500 $676,100 $1,432,400
2015 $6,911 $1,914,500 $619,200 $1,295,300
2014 $7,199 $1,914,500 $619,200 $1,295,300
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
10/27/2025 10/27/25 For Sale $4,000,000 -- $1,152 / Sq Ft
Source: LINK

Source: LINK

MLS Number: 92560

Massachusetts Nantucket County Nantucket 02554

27 Longwood Dr, Nantucket, MA

For Sale

Detached

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Listing Agent
Debbie Willett
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Great Point Properties
(508) 715-6667
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