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Off market
  • $17,443,000

    186 Windswept Way, Osterville, MA 02655

    8beds
    10,063sqft
    SingleFamily
    Built in 1933
    2.26 Acres Lot
    $17,443,000 Zestimate®
    $1,733/sqft
    $4,713 Estimated rent

    Home value

    $17,443,000

    $14.48M - $21.11M

    $4,713/mo

    Zestimate® history
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    Owner options

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    $4,713/mo

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    $4,713/mo

    Rent Zestimate®

    Refinance and save

    $104,262/mo

    Est. payment

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    $104,262/mo

    Est. payment

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    What's special

    Waterfront Legacy Property on Oyster Harbors! Perched on an elevated four-acre lot overlooking Cotuit Bay sits this striking example of a Tudor style residence designed by renowned Architect Clifford Allbright in 1933 and since beautifully maintained and updated in harmony with the original design. Refined architectural details set the tone in this grand home with over 10,000 sq. ft. of living space, an inground pool, a boathouse with extraordinary views, fireplace, sitting area and changing rooms, 437 linear feet of water frontage and a substantial deep-water dock, all combining to create an exceptionally rare offering in arguably one of the finest locations of Oyster Harbors. As you enter this home you will find yourself in a timeless and enchanting foyer that is equally refined with an impressive custom spiral staircase. Gracious formal living and dining rooms feature well-proportioned and spacious areas with soaring ceilings and wood and slate flooring, custom arched windows and doors and multiple fireplaces. Floor to ceiling walls of windows flood the rooms with natural light and beautiful water views are found throughout. A spacious great room anchors the home and provides

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 8
    • Bathrooms: 8
    • Full bathrooms: 6
    • 1/2 bathrooms: 2
    Heating
    • Forced air
    Cooling
    • Central
    Appliances
    • Included: Dishwasher, Dryer, Microwave, Refrigerator, Washer
    Interior area
    • Total interior livable area: 10,063 sqft

    Property

    Features
    • Exterior features: Brick
    Lot
    • Size: 2.26 Acres
    Details
    • Parcel number: OSTEM052L002

    Construction

    Type & style
    • Home type: SingleFamily
    Condition
    • Year built: 1933

    Utilities & green energy

    • Sewer: Private Sewer

    Community & neighborhood

    Location
    • Region: Osterville

    Other

    Other facts
    • Sewer: Private Sewer
    • Flood Ins Required: Unknown
    • Property Type: C
    • Property Sub-Type: Residential
    • Beach Description: Ocean, Harbor, Bay
    • Deed Restrictions: Yes
    • Miles to Beach: 0 - .1
    • Association Fee Incl: Snow Removal, Security, Rubbish Removal
    • Waterfront: Yes
    • Waterview: Yes
    • Waterfront Desc: Bay, Beach, Private, Salt, Ocean
    • Dock: Yes
    • Location Description: South of Route 28
    • Topography/Lot Desc: Level, View

    Price history

    DateEventPrice
    8/5/2022Sold$14,000,000-9.6%$1,391/sqft
    Source: MLS PIN #72880181
    7/8/2022Pending sale$15,495,000$1,540/sqft
    Source: CCIMLS #22104798
    5/26/2022Price change$15,495,000-7.8%$1,540/sqft
    Source: MLS PIN #72880181
    1/14/2022Price change$16,800,000-10.6%$1,669/sqft
    Source: CCIMLS #22104798
    8/17/2021Price change$18,800,000+11.9%$1,868/sqft
    Source: BHHS broker feed #22104798

    Public tax history

    YearProperty taxesTax assessment
    2025$91,745 +10.3%$11,340,600 +6.5%
    2024$83,194 +4.9%$10,652,300 +12%
    2023$79,292 -6%$9,507,400 +8.7%

    Find assessor info on the county website

    Neighborhood: Osterville

    Nearby schools

    GreatSchools rating
    Sell for more on Zillow
    Get a free Zillow Showcase℠ listing and you could sell for .
    $17.4M
    2% more+ $349K
    With Zillow Showcase(estimated)
    $17.8M