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Under contract
    • Price cut: $225K (6/29)
    $3,750,000

    27 Longwood Dr, Nantucket, MA 02554

    5beds
    3,472sqft
    : 
    $21,986/mo
    Get pre-qualified
    Single Family Residence
    Built in 1990
    2.75 Acres Lot
    $3,635,900 Zestimate®
    $1,080/sqft
    $33/mo HOA

    What's special

    Custom fireplaceCathedral ceilingTwo additional covered porchesUpside-down homeLarge dining areaDramatic curved staircaseGenerous foyer
    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.
    262 days
    |
    1,707
    |
    80
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Debbie Willett,

    Great Point Properties

    Source: LINK,MLS#: 92560

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      • Main level bedrooms: 3
      Heating
      • GFHA
      Appliances
      • Included: Stove: Yes, Washer: Yes 2
      Features
      • 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.
      • Flooring: Wood and Tile
      • Has fireplace: No
      • Fireplace features: 1
      • Furnished: Yes
      Interior area
      • Total structure area: 3,472
      • Total interior livable area: 3,472 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: Yes
      • Has garage: Yes
      Features
      • Exterior features: Deck, Porch, C/Tennis
      • Has view: Yes
      • View description: None, Pasture
      • Frontage type: None
      Lot
      • Size: 2.75 Acres
      • Features: See Document 1157 Title Number 5041 Electric Easement, Expansive Private Yard
      Details
      • Parcel number: 74
      • Zoning: LUG3

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Block
      Condition
      • Year built: 1990

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cbl

      Community & HOA

      HOA
      • Services included: $300 per year for tennis court use
      • HOA fee: $400 annually
      Location
      • Region: Nantucket

      Financial & listing details

      • Price per square foot: $1,080/sqft
      • Tax assessed value: $3,718,800
      • Annual tax amount: $12,195
      • Date on market: 10/27/2025
      • Listing agreement: E

        Estimated market value

        $3,635,900

        $3.45M - $3.82M

        $6,928/mo

        Price history

        DateEventPrice
        7/24/2026Contingent$3,750,000$1,080/sqft
        Source: LINK #92560 Report a problem
        6/29/2026Price change$3,750,000-5.7%$1,080/sqft
        Source: LINK #92560 Report a problem
        4/20/2026Listed for sale$3,975,000$1,145/sqft
        Source: LINK #92560 Report a problem
        4/10/2026Contingent$3,975,000$1,145/sqft
        Source: LINK #92560 Report a problem
        4/6/2026Price change$3,975,000-0.6%$1,145/sqft
        Source: LINK #92560 Report a problem
        10/27/2025Listed for sale$4,000,000+73.9%$1,152/sqft
        Source: LINK #92560 Report a problem
        5/14/2007Sold$2,300,000+1022%$662/sqft
        Source: LINK #65991 Report a problem
        9/11/1989Sold$205,000+24.2%$59/sqft
        Source: Public Record Report a problem
        12/1/1987Sold$165,000$48/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$12,198 +4.9%$3,718,800 +0.1%
        2024$11,629 +16.5%$3,715,300 +19.5%
        2023$9,981 +3.6%$3,109,300 +20.7%
        2022$9,632 +2%$2,575,400 -1%
        2021$9,443 +11.2%$2,601,400 +5.7%
        2020$8,495 +2.7%$2,462,200
        2019$8,273 -0.2%$2,462,200 +4.9%
        2018$8,286 +7.1%$2,347,300 +2.9%
        2017$7,735 +9.2%$2,281,800 +8.2%
        2016$7,085 +2.5%$2,108,500 +10.1%
        2015$6,911 -4%$1,914,500
        2014$7,199 -6.5%$1,914,500 -8.8%
        2013$7,703 +16%$2,099,000 +14.4%
        2012$6,640 +1.1%$1,834,300
        2011$6,567 +1.6%$1,834,300 -14.6%
        2010$6,464 +6.5%$2,147,500 -2.3%
        2009$6,070 +36.7%$2,199,100 +32.2%
        2008$4,442 +7.2%$1,663,700
        2007$4,143 +5.9%$1,663,700 +20.8%
        2006$3,912 +0.1%$1,377,600 +16.3%
        2005$3,908 +35.4%$1,184,100 +28.4%
        2004$2,886 +1.7%$921,900 +11.1%
        2003$2,839 +1%$830,100 +16.3%
        2001$2,812 $713,700
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 02554

        Getting around

        4 / 100
        Car-Dependent
        21 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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