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For sale
  • $3,000,000

    30 Chestnut Drive, Orleans, MA 02653

    4beds
    3,677sqft
    : 
    $17,730/mo
    Get pre-qualified
    Single Family Residence
    Built in 1998
    2.1 Acres Lot
    $2,824,000 Zestimate®
    $816/sqft
    $-- HOA

    What's special

    Wood-burning fireplaceDeeded beach accessBeautifully appointed kitchenCharming window seatLuxurious first-floor primary suiteFour-season sunroomSurrounded by mature landscaping
    Set on two private acres in one of East Orleans' most coveted Barley Neck neighborhoods, 30 Chestnut Drive is an exceptional Cape Cod retreat where refined interiors, resort-style outdoor living, and deeded beach access come together beautifully. Designed for both effortless everyday living and memorable gatherings, the home features four bedrooms and 3.5 baths, including a luxurious first-floor primary suite. The open-concept floor plan is anchored by a beautifully appointed kitchen with a generous center island, high-end appliances, and a butler's pantry. The adjoining living room, with custom built-ins, a charming window seat, and wood-burning fireplace, offers a warm and inviting place to gather, while the four-season sunroom brings the outdoors in throughout the year. A spacious bonus room above the garage provides wonderful flexibility for overflow guests, a home office, or additional recreation space. Outside, the property is truly extraordinary. The pool area feels like a five-star private oasis, surrounded by mature landscaping and generous space for lounging, dining, and entertaining. A private path leads to the neighborhood's deeded beach, making days on the water an effortless part of life here. Adding even more possibility is a separate cottage with electricity and a full foundation, offering exciting potential for conversion to an accessory dwelling unit, subject to Town approvals. Private yet close to the beaches, boating, and village amenities that make East Orleans so special, 30 Chestnut Road offers the space, setting, amenities, and lifestyle today's discerning buyers seek. This is Cape Cod living at its finest..
    26 days
    2,399
    226

    Zillow last checked:

    Listing updated:

    Listed by:

    Daneen Law 508-237-0977,

    Gibson Sotheby's International Realty

    Source: CCIMLS,MLS#: 22605085MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Heating
      • Oil
      Cooling
      • Central Air
      Appliances
      • Included: Oil, Water Heater
      Features
      • Flooring: Wood, Tile
      • Basement: Full
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 3,677
      • Total interior livable area: 3,677 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Direct Access, Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Stories: 2
      • Patio & porch: Patio, Porch, Screened Porch
      • Exterior features: Outdoor Shower
      • Has private pool: Yes
      Lot
      • Size: 2.1 Acres
      Details
      • Additional structures: Outbuilding
      • Parcel number: ORLE M:57 B: L:480
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Shingle Siding
      • Roof: Asphalt,Pitched
      Condition
      • Year built: 1998

      Utilities & green energy

      • Water: Well

      Community & HOA

      Location
      • Region: Orleans

      Financial & listing details

      • Price per square foot: $816/sqft
      • Tax assessed value: $2,088,500
      • Annual tax amount: $12,324
      • Date on market: 10/7/2026
      • Cumulative days on market: 26 days

        Estimated market value

        $2,824,000

        $2.68M - $2.97M

        $4,026/mo

        Price history

        DateEventPrice
        10/7/2026Listed for sale$3,000,000+156.4%$816/sqft
        Source: CCIMLS #22605085 Report a problem
        3/6/2015Sold$1,170,000-2.4%$318/sqft
        Source: CCIMLS #21411071 Report a problem
        12/28/2014Listed for sale$1,199,000+23.6%$326/sqft
        Source: oldCape Sotheby's International Realty #21411071 Report a problem
        2/16/2011Sold$970,000-2.9%$264/sqft
        Source: CCIMLS #21009559 Report a problem
        10/15/2010Listing removed$999,000$272/sqft
        Source: NCI #20907184 Report a problem
        7/2/2010Price change$999,000-8.3%$272/sqft
        Source: NCI #20907184 Report a problem
        6/11/2010Price change$1,090,000-4.4%$296/sqft
        Source: NCI #20907184 Report a problem
        5/27/2010Price change$1,140,000-4.2%$310/sqft
        Source: NCI #20907184 Report a problem
        5/15/2010Listed for sale$1,190,000-7.8%$324/sqft
        Source: NCI #20907184 Report a problem
        8/29/2009Listed for sale$1,290,000+658.8%$351/sqft
        Source: NCI #20907184 Report a problem
        3/17/1995Sold$170,000$46/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$11,686 +3.2%$1,872,700 +6%
        2024$11,328 +7.8%$1,767,200 +4.8%
        2023$10,508 +10%$1,686,700 +38.4%
        2022$9,553 $1,218,500
        2021$9,553 +4.2%$1,218,500 +0.5%
        2020$9,170 +8.5%$1,212,900 +6.2%
        2019$8,453 +16.4%$1,142,300 +4.3%
        2018$7,263 +6.8%$1,095,400 +1.9%
        2017$6,803 -10.8%$1,074,800 -9%
        2016$7,627 +1.9%$1,180,700 +1.3%
        2015$7,485 +3.5%$1,165,900
        2014$7,229 +1%$1,165,900 -0.6%
        2013$7,156 +6%$1,173,100 +2.7%
        2012$6,749 +5.5%$1,141,900 -0.6%
        2011$6,399 -14.8%$1,148,900 -21.2%
        2010$7,513 +5%$1,458,800 -0.5%
        2009$7,153 +16.6%$1,465,800 +8%
        2008$6,135 +6%$1,357,300 +0.2%
        2007$5,787 +2.1%$1,355,200 -0.5%
        2006$5,666 +3.8%$1,361,900 +9.5%
        2005$5,459 +2.5%$1,243,600 +2.9%
        2004$5,327 +5.2%$1,208,000 +22.1%
        2003$5,065 $989,200
        Find assessor info on the county website

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        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.
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        Climate risks

        Neighborhood: 02653

        Getting around

        4 / 100
        Car-Dependent
        23 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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