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For sale
    • Price cut: $80K (5/13)
    $2,395,000

    16 South Rd, Chilmark, MA 02535

    4beds
    2,350sqft
    : 
    $12,734/mo
    Get pre-qualified
    Single Family Residence
    Built in 1885
    1.6 Acres Lot
    $2,281,100 Zestimate®
    $1,019/sqft
    $-- HOA

    What's special

    Masonry double fireplacePreserved period detailsClassic barnHorse stallsTwo run-in horse stallsFenced fieldTwo main-level bedrooms
    Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian pursuits or a small gentleman’s farm—an increasingly uncommon offering in Chilmark at this price point. The open acreage invites outdoor living, from summer entertaining and gardening to quiet enjoyment of the surrounding landscape and privacy. Inside, the home balances antique charm with thoughtful updates. Four bedrooms and three full baths include two main-level bedrooms and two second-floor en-suite guest rooms, creating a comfortable and flexible layout for hosting family and friends. Living spaces are warm and inviting, with a masonry double fireplace, preserved period details, and an updated kitchen and baths. Recent improvements include HVAC, windows, insulation, and a five-bedroom septic system, offering flexibility for future expansion and barn renovation. Located steps from West Tisbury village, Alleys General Store, the library, the Yoga Barn, the Grange Hall and nearby conservation trails, the setting combines convenience with the privacy and natural beauty that define Chilmark. A distinctive Vineyard offering with uncommon versatility—equally suited as a summer retreat, year-round residence, or small-scale farmstead.
    142 days
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    549
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    27
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    Zillow last checked:

    Listing updated:

    Listed by:

    Michele Casavant,

    Vineyard Village Realty

    Source: LINK,MLS#: 44181

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      • Main level bedrooms: 2
      Heating
      • Propane
      Appliances
      • Included: Stove: Thermador, Washer: yes
      Features
      • AC, Ins, MiniSplit, Floor 1: Front and side foyer, two lounge areas, one with a masonry fireplace, cathedral ceiling and oversized for dining. A kitchen with a cathedral ceiling, and kitchen island, a full bath. A breaze way for additional storage of shoes, coats and sporting equipment. Two bedrooms., Floor 2: Two bedroom en-suites, each with their own bathroom., Floor 3: Attic space
      • Flooring: hardwood and tile
      • Basement: New full basement with laundry under the 1989 addition. Partial full basement with mechanical room under the original house, remainder is crawl.
      • Fireplace features: yes
      Interior area
      • Total structure area: 2,350
      • Total interior livable area: 2,350 sqft

      Property

      Parking
      • Parking features: plenty of off street parking
      Features
      • Exterior features: Deck, Garden, Patio, Porch
      • Has view: Yes
      • View description: None, Pasture
      • Frontage type: None
      Lot
      • Size: 1.6 Acres
      • Features: Boundary Line Agreement book 01373, page 0990, expansive large yard and field for horses, animals and gardneing
      Details
      • Additional structures: Large barn with electricity, two levels and garage area. Chicken coop and shed. Horse run-in barn with two stalls.
      • Parcel number: CHILM11P20
      • Zoning: RES

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: mixed-parital poured concrete, partial granite
      Condition
      • Year built: 1885
      • Major remodel year: 2018

      Utilities & green energy

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

      Community & HOA

      Location
      • Region: Chilmark

      Financial & listing details

      • Price per square foot: $1,019/sqft
      • Tax assessed value: $1,603,700
      • Annual tax amount: $4,100
      • Date on market: 3/9/2026
      • Listing agreement: E

        Estimated market value

        $2,281,100

        $2.17M - $2.40M

        $7,326/mo

        Price history

        DateEventPrice
        5/13/2026Price change$2,395,000-3.2%$1,019/sqft
        Source: LINK #44181 Report a problem
        3/28/2026Price change$2,475,000-1%$1,053/sqft
        Source: LINK #44181 Report a problem
        3/9/2026Listed for sale$2,500,000$1,064/sqft
        Source: LINK #44181 Report a problem
        12/15/2025Listing removed$2,500,000$1,064/sqft
        Source: LINK #43515 Report a problem
        9/16/2025Listed for sale$2,500,000$1,064/sqft
        Source: LINK #43515 Report a problem
        7/30/2025Listing removed$2,500,000$1,064/sqft
        Source: MLS PIN #73399410 Report a problem
        7/2/2025Listed for sale$2,500,000+24.3%$1,064/sqft
        Source: LINK #43515 Report a problem
        11/15/2023Sold$2,012,000+5.9%$856/sqft
        Source: LINK #41375 Report a problem
        10/3/2023Pending sale$1,900,000$809/sqft
        Source: LINK #41375 Report a problem
        9/29/2023Listed for sale$1,900,000+137.5%$809/sqft
        Source: LINK #41375 Report a problem
        4/17/2015Sold$800,000-11%$340/sqft
        Source: LINK #27378 Report a problem
        10/21/2014Listed for sale$899,000$383/sqft
        Source: Tea Lane Associates Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,714 +38.9%$1,650,500 +30.9%
        2024$2,673 +3.9%$1,261,000 +28.9%
        2023$2,572 +1%$977,900 +8.3%
        2022$2,546 +4.2%$902,900 +7.5%
        2021$2,444 +3.7%$840,000 +1.9%
        2020$2,357 +3.2%$824,000 +3.8%
        2019$2,285 +4.7%$793,500
        2018$2,182 +3.5%$793,500 +0.8%
        2017$2,109 +5%$787,100 +6.2%
        2016$2,009 $741,200
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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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.
        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: 02535

        Getting around

        28 / 100
        Car-Dependent
        33 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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