Skip main navigation
For sale
    • Price cut: $75K (8/25)
    $1,375,000

    345 North Rd, Chilmark, MA 02535

    5beds
    2,266sqft
    : 
    $7,763/mo
    Get pre-qualified
    Single Family Residence
    Built in 1981
    0.5 Acres Lot
    $1,338,100 Zestimate®
    $607/sqft
    $-- HOA

    What's special

    Natural buffer
    This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected conservation land of Menemsha Hills, the property enjoys a natural buffer along with direct access to scenic walking trails and some of Chilmark’s most iconic views. Ideally located just a short distance from Menemsha and Chilmark Center, it offers both seclusion and accessibility. Homeowners will also have access to Lucy Vinecent and Squibnocket beaches as Chilmark property owners. With an established rental history and full winterization for year-round use, this home is well-suited for both personal enjoyment and income generation. For those seeking a foothold in one of Martha’s Vineyard’s most desirable towns, this is a compelling opportunity not to be missed.
    146 days
    1,209
    71

    Zillow last checked:

    Listing updated:

    Listed by:

    Jessica Campbell,

    Flanders Real Estate

    Source: LINK,MLS#: 44126

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 5
      Heating
      • Heat Pump
      Appliances
      • Included: Stove: Yes, Washer: Yes
      Features
      • Ins, MiniSplit, OSh, WdStove, Floor 1: Entryway leads to the living room, Dining room, Kitchen with a smaller dining area, first-floor bathroom, Laundry, and utility closet., Floor 2: Up the stairs leads to 4 Bedrooms and 3 bathrooms, with a deck off the Primary suite, Floor 3: N/A
      • Flooring: Bamboo
      • Basement: Slab
      • Fireplace features: 3
      Interior area
      • Total structure area: 2,266
      • Total interior livable area: 2,266 sqft

      Property

      Parking
      • Parking features: Multiple spaces to park
      Features
      • Exterior features: PubBch, Deck, Patio
      • Has view: Yes
      • View description: None, Trees/Woods
      • Frontage type: None
      Lot
      • Size: 0.5 Acres
      • Features: Yes
      Details
      • Additional structures: Detached Guest bedroom with full bathroom and Kitchenette. Garage attached to the guest quarters.
      • Parcel number: CHILM20P38
      • Zoning: RES

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Concrete Slab
      Condition
      • Year built: 1981

      Utilities & green energy

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

      Community & HOA

      Location
      • Region: Chilmark

      Financial & listing details

      • Price per square foot: $607/sqft
      • Tax assessed value: $1,243,100
      • Annual tax amount: $3,449
      • Date on market: 4/20/2026
      • Listing agreement: E

        Estimated market value

        $1,338,100

        $1.27M - $1.41M

        Not available

        Price history

        DateEventPrice
        8/25/2026Price change$1,375,000-5.2%$607/sqft
        Source: LINK #44126 Report a problem
        7/3/2026Price change$1,450,000-6.5%$640/sqft
        Source: LINK #44126 Report a problem
        4/20/2026Listed for sale$1,550,000-4.6%$684/sqft
        Source: LINK #44126 Report a problem
        10/12/2025Listing removed$1,625,000$717/sqft
        Source: Martha's Vineyard MLS #32400300 Report a problem
        5/9/2025Price change$1,625,000-4.1%$717/sqft
        Source: Martha's Vineyard MLS #32400300 Report a problem
        2/22/2025Listed for sale$1,695,000-5.8%$748/sqft
        Source: Martha's Vineyard MLS #32400300 Report a problem
        10/27/2024Listing removed$1,800,000$794/sqft
        Source: LINK #42591 Report a problem
        10/11/2024Listed for sale$1,800,000+125%$794/sqft
        Source: LINK #42591 Report a problem
        11/25/2019Sold$800,000-3%$353/sqft
        Source: LINK #35429 Report a problem
        9/16/2019Price change$825,000-3.5%$364/sqft
        Source: Tea Lane Associates #35429 Report a problem
        7/4/2019Listed for sale$855,000+263.8%$377/sqft
        Source: Tea Lane Associates #35429 Report a problem
        2/25/1994Sold$235,000$104/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$2,797 +15.8%$1,243,100 +9.1%
        2024$2,415 +4.5%$1,139,000 +29.5%
        2023$2,312 +1.7%$879,200 +9%
        2022$2,274 +5%$806,300 +8.3%
        2021$2,166 +21.4%$744,200 +19.3%
        2020$1,784 +2.8%$623,800 +3.5%
        2019$1,735 +4.7%$602,500
        2018$1,657 +2.9%$602,500 +0.3%
        2017$1,610 -0.6%$600,900 +0.6%
        2016$1,619 $597,500
        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.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 02535

        Getting around

        3 / 100
        Car-Dependent
        3 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        A local lender can help you make sure your offer is ready when you are.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby zip codes

              Other Chilmark Topics

                Search
                Updates
                Favorites
                Plan
                Inbox