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For sale
  • Price cut: $100K (8/22)
    $1,095,000

    2 Winemack Street, Oak Bluffs, MA 02557

    3beds
    2,173sqft
    : 
    $6,220/mo
    Get pre-qualified
    Single Family Residence
    Built in 1988
    4,791 Square Feet Lot
    $1,060,600 Zestimate®
    $504/sqft
    $-- HOA

    What's special

    Small manageable yardOff-street parking
    Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home's usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed "doghouse"-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to cover costs(to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.
    15 days
    1,217
    38

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Rene A Ben David 508-847-4864,

    Ocean Park Realty, Inc.

    Source: CCIMLS,MLS#: 22603994MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      • Main level bathrooms: 1
      Heating
      • Hot Water
      Cooling
      • None
      Appliances
      • Included: Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Microwave, Electric Dryer
      Features
      • Flooring: Other, Tile, Laminate
      • Basement: Bulkhead Access,Interior Entry,Finished
      • Has fireplace: No
      Interior area
      • Total structure area: 2,173
      • Total interior livable area: 2,173 sqft

      Property

      Parking
      • Total spaces: 3
      • Parking features: Open
      • Has uncovered spaces: Yes
      Features
      • Stories: 2
      • Patio & porch: Deck
      • Exterior features: Outdoor Shower
      Lot
      • Size: 4,791 Square Feet
      • Features: Marina, Medical Facility, Shopping
      Details
      • Parcel number: OAKB M:0004 B:0126 L:000
      • Zoning: R1
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod, Shingle
      • Property subtype: Single Family Residence
      Materials
      • Shingle Siding
      • Foundation: Poured
      • Roof: Asphalt, Pitched
      Condition
      • Updated/Remodeled, Actual
      • New construction: No
      • Year built: 1988
      • Major remodel year: 2026

      Utilities & green energy

      • Sewer: Septic Tank, Septic Tank

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Oak Bluffs

      Financial & listing details

      • Price per square foot: $504/sqft
      • Tax assessed value: $998,700
      • Annual tax amount: $4,092
      • Date on market: 8/15/2026
      • Cumulative days on market: 19 days
      • Road surface type: Paved

        Estimated market value

        $1,060,600

        $1.01M - $1.11M

        $6,805/mo

        Price history

        DateEventPrice
        8/22/2026Price change$1,095,000-8.4%$504/sqft
        Source: LINK #44805 Report a problem
        8/12/2026Listed for sale$1,195,000$550/sqft
        Source: LINK #44805 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,877 +1.2%$965,700 +4.8%
        2024$4,818 -4.7%$921,200 -3.8%
        2023$5,056 +1.5%$957,500 +30.5%
        2022$4,983 +15.5%$733,900 +25.3%
        2021$4,316 +5.4%$585,600 +6.4%
        2020$4,095 +1.7%$550,400 +5.1%
        2019$4,026 +9.2%$523,500 +11.2%
        2018$3,687 +6.1%$470,900 +10.4%
        2017$3,475 +7.8%$426,400 +7.2%
        2016$3,225 +6.3%$397,600 +4.3%
        2015$3,035 +6.5%$381,300 +4.5%
        2014$2,849 -3.7%$364,800 -4.9%
        2013$2,958 +4.3%$383,600
        2012$2,835 +7.3%$383,600 +2.1%
        2011$2,641 -6.1%$375,700 -15.9%
        2010$2,814 -0.6%$446,700 -4.7%
        2009$2,831 +7.3%$468,700
        2008$2,639 +1.8%$468,700 +1%
        2007$2,593 +7.6%$463,900 +10.7%
        2006$2,409 +12.2%$418,900 +18.4%
        2005$2,148 +5.1%$353,800 +121.5%
        2001$2,044 $159,700
        Find assessor info on the county website

        Monthly payment

        Est. payment

        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 02557

        Getting around

        15 / 100
        Car-Dependent
        41 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Martha's Vineyard

        Source: CCIMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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