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Pending
    • $3,750,000

    139 Main St, Tisbury, MA 02568

    5beds
    4,372sqft
    : 
    $22,386/mo
    Get pre-qualified
    Single Family Residence
    Built in 1840
    0.54 Acres Lot
    $3,393,400 Zestimate®
    $858/sqft
    $-- HOA

    What's special

    Single half-acre parcelWelcoming vestibuleCustom cabinetryRich woodworkOversized windowsGenerously proportioned roomsStone countertops
    Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages. From the moment you step through the welcoming vestibule, it’s clear this is a home with stories to tell. Wood plank floors, rich woodwork, and generously proportioned rooms speak to its heritage, while thoughtful updates have introduced an easy, understated luxury throughout. The kitchen has been beautifully remodeled with custom cabinetry and stone countertops. Light pours through oversized windows into gracious living and dining spaces, with a fireplace adding warmth and character to the living room. Upstairs, the primary suite offers garden views and a peaceful retreat, while guest bedrooms retain period charm with airy, sunlit appeal. Outside, the grounds feel secluded and mature—a private world behind an original wrought iron gate. Paths wind through perennial gardens and wide lawns, while a porch and flagstone patio invite lingering afternoons in the dappled shade. A charming one-bedroom guest cottage sits tucked away from the main house, offering flexibility for guests, work-from-home, or rental income. This home has long been cherished by artists, collectors, and careful stewards—each adding their layer to the property’s quiet patina. Just a short stroll to the ferry, shops, restaurants, library, and beach, 139 Main Street is a rare find: a truly in-town retreat that feels a world apart. This expansive main house offers flexible living with six rooms currently used as bedrooms, including a separate guest suite. The property has a 5-bedroom septic system per Title 5.
    58 days
    |
    99
    |
    3
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Leslie C. Floyd 508-221-4643,

    Portfolio Properties

    Source: LINK,MLS#: 44486

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 7
      • Full bathrooms: 6
      • 1/2 bathrooms: 1
      Heating
      • Heat Pump
      Appliances
      • Included: Stove: Viking, Washer: Yes
      Features
      • Ins, Irr, MiniSplit, OSh, Floor 1: Gracious living with stunning stone fireplace and dining room with original built-in cupboard and wood plank floors, renovated kitchen with custom cabinetry and stone countertops, large porch, office/den, and half bath. Large windows throughout provide abundant natural light., Floor 2: Primary suite with updated bath and garden views, four additional bedrooms-two with baths ensuite, a full shared hall bath, and two cozy sitting nooks—all filled with period charm and original detailing., Floor 3: Finished attic space with full bath, and expansive mahogany deck offering flexible use as guest rooms, office, or creative studio. Bright and airy with dormer windows and tucked-away charm. One room boasts a fireplace.
      • Flooring: Hardwood and tile
      • Basement: Unfinished basement with interior access and exterior walk in access ideal for outdoor furniture, bicycle and boat storage. Houses updated systems and utilities.
      • Fireplace features: 2 Wood burning
      Interior area
      • Total structure area: 4,372
      • Total interior livable area: 4,372 sqft

      Property

      Parking
      • Parking features: Ample Off Street Parking
      Features
      • Exterior features: WViews, Deck, Porch, PubBch, Patio
      • Has view: Yes
      • View description: Harbor, Twn
      • Has water view: Yes
      • Water view: Harbor
      • Frontage type: None
      Lot
      • Size: 0.54 Acres
      • Features: Expansive Yard
      Details
      • Additional structures: Detached 1-bedroom, 1-bath guest cottage offers privacy and flexibility for guests, work-from-home, or rental income.
      • Parcel number: TISBM0006CB00000L0301
      • Zoning: R25

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Stone / Brick / Concrete
      Condition
      • Year built: 1840
      • Major remodel year: 2017

      Utilities & green energy

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

      Community & HOA

      Location
      • Region: Tisbury

      Financial & listing details

      • Price per square foot: $858/sqft
      • Tax assessed value: $2,679,100
      • Annual tax amount: $21,065
      • Date on market: 5/15/2026
      • Listing agreement: E

        Estimated market value

        $3,393,400

        $3.22M - $3.56M

        $7,564/mo

        Price history

        DateEventPrice
        7/9/2026Pending sale$3,750,000$858/sqft
        Source: LINK #44486 Report a problem
        5/14/2026Listed for sale$3,750,000$858/sqft
        Source: CCIMLS #22602196 Report a problem
        1/2/2026Listing removed$3,750,000$858/sqft
        Source: Martha's Vineyard MLS #32500243 Report a problem
        8/26/2025Price change$3,750,000-5.1%$858/sqft
        Source: Martha's Vineyard MLS #32500243 Report a problem
        7/17/2025Listed for sale$3,950,000+125.7%$903/sqft
        Source: LINK #43531 Report a problem
        3/24/2021Listing removed--
        Source: Owner Report a problem
        11/21/2008Listing removed$1,750,000$400/sqft
        Source: Owner Report a problem
        8/1/2008Price change$1,750,000+6.1%$400/sqft
        Source: Owner Report a problem
        6/25/2008Price change$1,650,000-5.7%$377/sqft
        Source: Owner Report a problem
        5/9/2008Price change$1,750,000+99900%$400/sqft
        Source: Owner Report a problem
        2/26/2008Listed for sale$1,750-99.6%
        Source: Owner Report a problem
        8/25/1993Sold$393,000$90/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$20,281 -3.7%$2,679,100 +1.5%
        2024$21,064 +17.4%$2,639,600 +7.7%
        2023$17,947 +10.9%$2,451,800 +31.8%
        2022$16,189 -7.2%$1,860,817 -2.2%
        2021$17,450 -5.1%$1,902,900 -3.5%
        2020$18,390 +1.9%$1,971,100 +0.2%
        2019$18,039 +23.1%$1,967,200 +26.9%
        2018$14,654 -10.2%$1,550,700 -13.5%
        2017$16,323 +31.4%$1,791,800 +32.1%
        2016$12,426 -18.1%$1,356,500 -20.2%
        2015$15,169 +31.5%$1,700,600 +23.7%
        2014$11,533 +7.4%$1,374,600 +8.5%
        2013$10,739 +0.8%$1,266,400 -4.7%
        2012$10,649 +15.4%$1,329,500 +8.3%
        2011$9,231 -0.4%$1,227,500 -13%
        2010$9,272 +9.5%$1,411,300 -0.3%
        2009$8,469 +7.9%$1,416,200 -1%
        2008$7,851 -0.3%$1,430,100 +2.3%
        2007$7,871 +11.9%$1,398,000 +3.4%
        2006$7,032 -2.7%$1,352,300 +9.7%
        2005$7,227 +24.1%$1,233,200 +71.4%
        2004$5,822 +4.7%$719,600
        2003$5,563 +5.6%$719,600
        2002$5,267 -2.5%$719,600 +78.1%
        2000$5,401 $404,000
        Find assessor info on the county website

        Monthly payment

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        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: 02568

        Getting around

        71 / 100
        Very Walkable
        65 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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