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For sale
    • Price increase: $482K (7/15)
    $2,600,000

    111 Eastville Ave, Oak Bluffs, MA 02557

    6beds
    2,400sqft
    : 
    $14,432/mo
    Get pre-qualified
    Single Family Residence
    Built in 1859
    0.43 Acres Lot
    $2,428,200 Zestimate®
    $1,083/sqft
    $-- HOA

    What's special

    LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES. Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous accommodations for family, friends, and guests. From the EXPANSIVE ROOFTOP entertainment deck, enjoy sweeping 180-degree water views of Vineyard Haven Harbor — a spectacular vantage point for watching ferries and sailboats glide by at sunset. Originally built in 1859 by noted whaling captain Shaw Norris, this classic Greek Revival residence seamlessly blends historic character with modern luxury. Extensive renovations — including a new roof, siding, trim, and all-new mechanical systems — have transformed the property into a home that lives like new construction while preserving its architectural integrity, ensuring peace of mind for years to come. The open-concept first floor is thoughtfully designed for effortless entertaining, anchored by a gourmet kitchen that flows seamlessly to a private outdoor dining area. Two first-floor ensuite bedrooms provide exceptional flexibility: one showcasing original architectural details and a historic hearth, the other offering a private entrance and a secluded patio porch. Upstairs, a comfortable lounge opens to a spacious recreation area, creating the ideal setting for gathering and relaxation. Land Bank–protected parcels on two sides of the property enhance privacy and preserve the serene coastal setting. Whether you’re seeking a high-performing investment property or a generational family compound, this one-of-a-kind residence offers timeless charm, breathtaking water views, and modern comfort in a premier Martha's Vineyard location. Broker has an ownership interest in the property.
    317 days
    |
    780
    |
    16
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Ed Charter,

    Arrowhead Homes

    Source: LINK,MLS#: 36870

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 4
      • Full bathrooms: 4
      • Main level bedrooms: 2
      Heating
      • Heat Pump
      Appliances
      • Included: Stove: Yes, Washer: Yes
      Features
      • AC, Ins, MiniSplit, OSh, Floor 1: This home radiates timeless charm and effortless comfort. The open-concept living room, dining area, and kitchen flow beautifully together, creating a warm and inviting gathering space. A generous window seat draws in natural light and offers the perfect spot to relax and unwind. Just off the kitchen, step onto a private outdoor dining patio overlooking the Land Bank’s serene wooded landscape — an ideal setting for quiet mornings or evening entertaining. On the first floor, one bedroom suite captures historic character with original wide-plank flooring, an authentic brick fireplace, and a spacious bath featuring a striking Italian marble shower. The second suite blends luxury and privacy, showcasing distinctive Canary wood floors, a private entrance, and an elegant Carrara marble bathroom. Thoughtfully designed and rich in detail, this home seamlessly combines historic beauty with refined modern comfort., Floor 2: The second floor offers four comfortable bedrooms and two charming bathrooms, providing plenty of space for family and guests. A highlight of this level is the inviting lounge area, complete with comfortable seating, a flat-screen TV, and a refrigerator—perfect for relaxing or casual entertaining. One of the bedrooms opens to a private, shaded outdoor lounge, ideal for morning coffee or quiet reflection. An additional adjacent lounge area provides extra outdoor seating, perfect for enjoying gentle breezes and tranquil tree views., Floor 3: One of the home’s most impressive features is its expansive rooftop deck, complete with a gas firepit and a gas barbecue. This spectacular space is perfect for entertaining guests, hosting gatherings, or simply unwinding in style. Enjoy sunrise breakfasts or epic sunsets from this elevated entertainment area, where panoramic views create an unforgettable experience.
      • Flooring: 2
      • Basement: insulated Crawl Space
      • Fireplace features: 1
      • Furnished: Yes
      Interior area
      • Total structure area: 2,400
      • Total interior livable area: 2,400 sqft

      Property

      Parking
      • Parking features: Plentiful Parking
      Features
      • Exterior features: WViews, Deck, PubBch, Porch
      • Has view: Yes
      • View description: Harbor, Sound
      • Has water view: Yes
      • Water view: Harbor,Sound
      • Frontage type: None
      Lot
      • Size: 0.43 Acres
      • Features: Yes
      Details
      • Additional structures: There is a small garage and a storage shed.
      • Parcel number: 13
      • Zoning: R1

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Crawl space
      Condition
      • Year built: 1859
      • Major remodel year: 2020

      Utilities & green energy

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

      Community & HOA

      Location
      • Region: Oak Bluffs

      Financial & listing details

      • Price per square foot: $1,083/sqft
      • Tax assessed value: $2,285,300
      • Annual tax amount: $4,144
      • Date on market: 5/5/2025
      • Listing agreement: E

        Estimated market value

        $2,428,200

        $2.31M - $2.55M

        $7,977/mo

        Price history

        DateEventPrice
        7/15/2026Price change$2,600,000+22.8%$1,083/sqft
        Source: LINK #36870 Report a problem
        6/30/2026Price change$2,118,000-15.2%$883/sqft
        Source: LINK #36870 Report a problem
        6/9/2026Listed for sale$2,499,000-3.8%$1,041/sqft
        Source: LINK #36870 Report a problem
        1/5/2026Listing removed$2,599,000$1,083/sqft
        Source: LINK #36870 Report a problem
        12/16/2025Price change$2,599,000-1.9%$1,083/sqft
        Source: LINK #36870 Report a problem
        9/29/2025Price change$2,649,000-1.9%$1,104/sqft
        Source: LINK #36870 Report a problem
        8/5/2025Price change$2,699,000-1.8%$1,125/sqft
        Source: LINK #36870 Report a problem
        6/4/2025Price change$2,748,000-1.8%$1,145/sqft
        Source: LINK #36870 Report a problem
        5/5/2025Listed for sale$2,798,000-12.6%$1,166/sqft
        Source: LINK #36870 Report a problem
        12/12/2023Listing removed$3,200,000$1,333/sqft
        Source: LINK #41243 Report a problem
        10/6/2023Listed for sale$3,200,000+381.2%$1,333/sqft
        Source: LINK #41243 Report a problem
        7/26/2019Sold$665,000+42.2%$277/sqft
        Source: LINK #35637 Report a problem
        6/17/2014Sold$467,500+67%$195/sqft
        Source: LINK #19167 Report a problem
        10/10/1997Sold$280,000$117/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$11,541 +47%$2,285,300 +52.2%
        2024$7,852 +0.2%$1,501,400 +1.2%
        2023$7,835 +27.6%$1,483,900 +64.1%
        2022$6,140 +11.4%$904,300 +20.9%
        2021$5,514 +33%$748,200 +34.3%
        2020$4,146 -0.1%$557,300 +3.3%
        2019$4,150 +2.8%$539,700 +4.7%
        2018$4,036 -7.8%$515,500 -4%
        2017$4,378 +5.7%$537,200 +5.2%
        2016$4,142 -1.2%$510,700 -3%
        2015$4,192 $526,600
        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.
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        Climate risks

        Neighborhood: 02557

        Getting around

        15 / 100
        Car-Dependent
        42 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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