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Pending
    • $2,180,000

    25 Pennacook Ave, Oak Bluffs, MA 02557

    4beds
    2,516sqft
    : 
    $12,246/mo
    Get pre-qualified
    Single Family Residence
    Built in 1999
    3,485 Acres Lot
    $2,069,100 Zestimate®
    $866/sqft
    $-- HOA

    What's special

    Additional third shower
    A unique offering in the heart of the historic Copeland District of downtown Oak Bluffs. This cherished main residence and guest house, embody the timeless charm that defines this beloved community. Just minutes from Circuit Ave, the ferries and harbor, and a block from Inkwell Beach. This home invites you to experience the essence of Oak Bluffs! The main house, dating back to the 1850s, has been well maintained, preserving its period architectural details while incorporating modern updates, including an updated kitchen with a walk-in pantry. At the heart of the home, a classic stone fireplace anchors the living and dining areas, creating an inviting gathering space. On the second floor, the primary suite gives a sense of grandeur and charm, with a vaulted ceiling, chandelier and multiple closets. The bathroom includes a soaking tub and separate water closet. Two more bedrooms and a shared full bath provide comfortable accommodations for family and visitors. The second floor is thoughtfully centered around a laundry area, complete with an additional third shower for added convenience. The guest cottage is a sweet retreat~ built in 1999. The first floor features a full kitchen, living room, and half bath, along with a convenient stackable washer and dryer. Upstairs, the second floor offers a one-bedroom layout with an adjoining dressing room or office area that leads to a full bath. Hardwood floors run throughout and forced hot water heating allows for comfortable year-round use. The guest house and the main house share the rear deck, and an outdoor shower that's perfect for island living. The properties are connected to town sewer and equipped for year-round use with a heating and A/C Viessmann system for efficiency. When in bloom, blue hydrangeas frame the properties, enhancing their classic Vineyard charm. Both homes feature quintessential front porches, ideal for greeting neighbors and enjoying the island community. This an opportunity to become a part of this enduring legacy and create lasting memories for generations to come. With a strong rental history, this property presents a great investment opportunity too!
    46 days
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    89
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    Zillow last checked:

    Listing updated:

    Listed by:

    Nya Clarke, 508-572 -3636 call /text,

    Martha's Vineyard Island-Wide Realty

    Source: LINK,MLS#: 44285

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 3
      • 1/2 bathrooms: 2
      Heating
      • GFHW
      Appliances
      • Included: Stove: Forno Eight burner gas stove in main house, Washer: Main House has a hallway laundry area with washer (Guest Hse -1 washer)
      Features
      • AC, Ins, Irr, MiniSplit, OSh, WdStove, Floor 1: The main house, dating back to 1850, features a classic wraparound front porch and an original stained glass front door. Inside, an open living and dining area is centered around a stone hearth fireplace with a cast-iron potbelly wood stove insert. The living room has custom bookshelves and original brass lighting fixtures throughout highlighting the era of this home. The updated kitchen has an eight-burner gas stove and a spacious pantry, with a convenient half bath located just off the kitchen. The back door leads to the shared 300sq ft rear deck with outdoor shower, and two off-street parking spots to further enhance the property’s appeal. Notable preserved Victorian details such as period woodwork, pocket doors, stained glass, porcelain sinks, antique lighting and doors with original hardware (the house has been updated with recessed lighting too), Floor 2: The main staircase off the dining area leads to the primary suite, featuring a vaulted ceiling, chandelier, and multiple closets, along with an en suite bath complete with a soaking tub and separate water closet. Two additional spacious bedrooms and a shared full bath offer comfortable accommodations for family and guests. The second floor also includes a centrally located laundry area with a washer and dryer, an additional third shower, and a dedicated storage space.
      • Flooring: Hardwood floors throughout both properties
      • Basement: Access to the main house basement cellar is located off the kitchen. In the cellar is a Viessmann heating system (Gas-FHW) hot water heater and electric panel.
      • Fireplace features: One stone fireplace with wood stove insert in the main house dining area
      • Furnished: Yes
      Interior area
      • Total structure area: 2,516
      • Total interior livable area: 2,516 sqft

      Property

      Parking
      • Parking features: 2 off street parking spots
      Features
      • Exterior features: Porch, PubBch, Deck, C/Tennis
      • Has view: Yes
      • View description: None, Res
      • Frontage type: None
      Lot
      • Size: 3,485 Acres
      • Features: Blue hydrangeas lined perimeter of the property, maintained w/ irrigation
      Details
      • Additional structures: *see guest house info House is being sold turnkey with a sellers exclusion list for personal items.
      • Parcel number: 0
      • Zoning: R1

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Cellar in main house and basement in guest house
      Condition
      • Year built: 1999
      • Major remodel year: 2008

      Utilities & green energy

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

      Community & HOA

      HOA
      • Services included: current sewer betterment usage fee: $1458.00 yrly
      Location
      • Region: Oak Bluffs

      Financial & listing details

      • Price per square foot: $866/sqft
      • Tax assessed value: $1,866,700
      • Annual tax amount: $9,579
      • Date on market: 4/11/2026
      • Listing agreement: E

        Estimated market value

        $2,069,100

        $1.97M - $2.17M

        $7,723/mo

        Price history

        DateEventPrice
        6/1/2026Pending sale$2,180,000$866/sqft
        Source: LINK #44285 Report a problem
        5/26/2026Contingent$2,180,000$866/sqft
        Source: LINK #44285 Report a problem
        4/11/2026Listed for sale$2,180,000+1171.1%$866/sqft
        Source: LINK #44285 Report a problem
        10/9/1997Sold$171,500$68/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,136 +5.1%$1,809,200 +8.8%
        2024$8,693 +3.2%$1,662,200 +4.2%
        2023$8,422 +6%$1,595,000 +36.3%
        2022$7,947 +8.1%$1,170,400 +17.4%
        2021$7,350 +5.9%$997,300 +6.9%
        2020$6,942 +1.1%$933,000 +4.5%
        2019$6,864 +2.1%$892,600 +3.9%
        2018$6,724 +4.1%$858,800 +8.4%
        2017$6,459 +8.5%$792,500 +7.9%
        2016$5,954 +7.7%$734,200 +5.7%
        2015$5,529 -3.8%$694,600 -5.7%
        2014$5,750 +13.1%$736,200 +11.7%
        2013$5,082 +2.2%$659,200 -2.1%
        2012$4,975 -1.2%$673,200 -6%
        2011$5,036 +5.6%$716,400 -5.4%
        2010$4,770 +6%$757,200 +1.6%
        2009$4,502 +7.3%$745,300
        2008$4,196 -9.7%$745,300 -10.4%
        2007$4,648 $831,500
        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.
        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: 02557

        Getting around

        63 / 100
        Somewhat Walkable
        44 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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