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For sale
  • $16,500,000

    143 Bayberry Way, Osterville, MA 02655

    8beds
    8,763sqft
    : 
    $108,517/mo
    Get pre-qualified
    Single Family Residence
    Built in 1914
    3.02 Acres Lot
    $12,875,100 Zestimate®
    $1,883/sqft
    $-- HOA

    What's special

    Refined architectural details throughoutLarge private estate settingsInviting pebbletech-finish poolGourmet kitchenExtensive custom millworkMagnificent western exposureWarm luxurious living spaces
    Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate settings. This property also benefits from protected conservation 'Land Trust' land directly across from its gated entrance to the property. The main residence encompasses warm, luxurious living spaces, distinguished by extensive custom millwork, custom stone, tile and brick work, and refined architectural details throughout. The gourmet kitchen and butler's pantry are designed to delight, while the grand living room and adjoining dining room provide an elegant setting for entertaining. A sunroom overlooks the water, while the inviting family room and adjacent dining area create comfortable spaces for everyday living. The residence offers a 1st floor bedroom suite, and the 2nd floor provides three bedroom suites and a glorious master suite with his-and-her bathrooms and dressing rooms, a private sitting room, and a deck with exceptional water views. The third floor features an additional bedroom and bath, a family room, and a charming widow's walk overlooking the surrounding landscape and bay. A finished lower level provides additional flexible living and recreational space. A separate two-bedroom, two-bath carriage house offers a full kitchen and living room, providing an ideal private retreat for guests and extended family. Encompassing three acres of beautifully landscaped, park-like grounds, that are irrigated by a private well, the property offers an extraordinary sense of privacy. Manicured lawns and gracious mature trees frame an inviting PebbleTech-finish pool, an expansive terrace, perfectly suited for outdoor entertaining and enjoying unforgettable sunsets. Steps lead down to the water's edge, where a private sitting area provides a peaceful place to take in the views. A permanent deep-water dock on West Bay complete this remarkable waterfront setting. The prestigious Wianno Club and Oyster Harbors Club, as well as Nauticus Yacht Club, Crosby Boatyard, and the numerous shops and restaurants in the village, are only minutes away. All information stated here in or verbally stated, should be verified by the Buyer(s) and their representatives.
    4 days
    816
    89

    Zillow last checked:

    Listing updated:

    Listed by:

    John J Hopkins 508-320-9461,

    Frank A Sullivan Real Estate

    Source: CCIMLS,MLS#: 22605034MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 8
      • Bathrooms: 11
      • Full bathrooms: 9
      • 1/2 bathrooms: 2
      Heating
      • Natural Gas
      Cooling
      • Central Air
      Appliances
      • Included: Natural Gas, Water Heater
      Features
      • Recessed Lighting, Walk-In Closet(s)
      • Flooring: Wood, Tile
      • Basement: Finished,Full
      • Number of fireplaces: 3
      Interior area
      • Total structure area: 8,763
      • Total interior livable area: 8,763 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Detached, Garage Door Opener, Driveway, Gravel
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Stories: 3
      • Patio & porch: Patio
      • Exterior features: Underground Sprinkler System
      • Has private pool: Yes
      • On waterfront: Yes
      • Waterfront features: Waterview, Waterfront, Bay/Harbor
      • Body of water: West Bay,Salt
      Lot
      • Size: 3.02 Acres
      Details
      • Parcel number: OSTE M:0091 B:0009 L:0000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Shingle Siding
      • Roof: Wood,Shingle
      Condition
      • Year built: 1914

      Utilities & green energy

      • Water: Well, Public

      Community & HOA

      Location
      • Region: Osterville

      Financial & listing details

      • Price per square foot: $1,883/sqft
      • Tax assessed value: $9,636,700
      • Annual tax amount: $78,577
      • Date on market: 10/2/2026
      • Cumulative days on market: 5 days

        Estimated market value

        $12,875,100

        $10.43M - $15.84M

        Not available

        Price history

        DateEventPrice
        10/2/2026Listed for sale$16,500,000+106.3%$1,883/sqft
        Source: CCIMLS #22605034 Report a problem
        4/10/2013Sold$8,000,000-17.9%$913/sqft
        Source: CCIMLS #21105684 Report a problem
        10/11/2012Listed for sale$9,750,000-7.1%$1,113/sqft
        Source: Robert Paul Properties, Inc #71252230 Report a problem
        3/5/2012Listed for sale$10,500,000-16%$1,198/sqft
        Source: Robert Paul Properties, Inc #71252230 Report a problem
        6/22/2011Listed for sale$12,500,000+237.8%$1,426/sqft
        Source: Robert Paul Properties, Inc #71252230 Report a problem
        11/15/1989Sold$3,700,000$422/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$98,446 +6.3%$12,168,800 +2.7%
        2024$92,574 +4%$11,853,300 +11.1%
        2023$89,007 +32.7%$10,672,300 +53.3%
        2022$67,092 -0.8%$6,959,800 +8%
        2021$67,600 -6.2%$6,444,200 -2%
        2020$72,067 +8.4%$6,575,500 +11.6%
        2019$66,463 +0.9%$5,892,100 +0.4%
        2018$65,856 +4.9%$5,869,500 +0.6%
        2017$62,764 -1.3%$5,833,100
        2016$63,581 +2.3%$5,833,100 +1.8%
        2015$62,163 +7.9%$5,729,300 +5.7%
        2014$57,622 +15.8%$5,420,700 +11.6%
        2013$49,739 -0.2%$4,857,300 -4%
        2012$49,834 +2.7%$5,059,300 -2.2%
        2011$48,513 -6.6%$5,172,000 -10.1%
        2010$51,933 -11.2%$5,751,200 -21.5%
        2009$58,465 +1.7%$7,326,500 -3%
        2008$57,506 +20.3%$7,556,600 -0.1%
        2007$47,786 +8.7%$7,561,000 +8.5%
        2006$43,980 +10.8%$6,969,900 +6.2%
        2005$39,689 -37.6%$6,560,200 +15.8%
        2004$63,555 $5,664,400
        2003$63,555 +50.1%$5,664,400 +20.2%
        2001$42,349 +14.3%$4,710,700 +53.8%
        1997$37,035 $3,063,300
        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: Osterville

        Getting around

        3 / 100
        Car-Dependent
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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