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Off market
  • $9,008,600

    42 Contentment Island Rd, Darien, CT 06820

    6beds
    6,449sqft
    SingleFamily
    Built in 1900
    3.21 Acres Lot
    $9,008,600 Zestimate®
    $1,397/sqft
    $41,394 Estimated rent

    Home value

    $9,008,600

    $7.39M - $11.08M

    $41,394/mo

    Zestimate® history
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    Owner options

    List your home for rent

    $41,394/mo

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    $41,394/mo

    Rent Zestimate®

    Refinance and save

    $60,863/mo

    Est. payment

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    $60,863/mo

    Est. payment

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    What's special

    Sensational direct waterfront property located in the private Tokeneke Association. This magnificent Tudor home includes 3.2 secluded acres at the end of Contentment Island with extra lot potential. A dock and tennis court make this a perfect setting to enjoy outdoor activities on Scott's Cove and L.I. Sound. Built in 1900, the architectural integrity remains while updates have embraced its waterfront location and surrounding trees. Large picture windows, French doors, a seaside terrace and covered porch bring the outside in to this beloved home. Upstairs are 5 bedrooms, a family room and an office with a view all its own. Sea breezes fill the master suite with sitting room. A one-bedroom waterfront cottage is above the 3-car garage.

    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: 6
    • Bathrooms: 5
    • Full bathrooms: 4
    • 1/2 bathrooms: 1
    Heating
    • Other, Oil
    Features
    • Basement: Dugout
    • Has fireplace: Yes
    Interior area
    • Total interior livable area: 6,449 sqft

    Property

    Parking
    • Parking features: Garage - Attached
    Features
    • Exterior features: Stucco, Brick
    Lot
    • Size: 3.21 Acres
    Details
    • Parcel number: DARIM68B26

    Construction

    Type & style
    • Home type: SingleFamily
    Materials
    • Foundation: Crawl/Raised
    Condition
    • Year built: 1900

    Community & neighborhood

    Community
    • Community features: On Site Laundry Available
    Location
    • Region: Darien

    HOA & financial

    HOA
    • Has HOA: Yes
    • HOA fee: $306 monthly

    Price history

    DateEventPrice
    7/26/2018Price change$7,250,000-18.1%$1,124/sqft
    Source: Halstead Real Estate #99157920 Report a problem
    5/3/2018Price change$8,850,000-10.2%$1,372/sqft
    Source: Halstead Real Estate #99157920 Report a problem
    1/25/2018Price change$9,850,000-12.1%$1,527/sqft
    Source: Halstead Property #99157920 Report a problem
    8/25/2016Listed for sale$11,200,000+474.4%$1,737/sqft
    Source: Halstead Property #32033 Report a problem
    5/5/1993Sold$1,950,000$302/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$81,105 +5.4%$5,239,360
    2024$76,966 -7%$5,239,360 +11.5%
    2023$82,725 +2.2%$4,697,630

    Find assessor info on the county website

    Neighborhood: Tokeneke

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Tokeneke
    • High: Darien

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

    Sell for more on Zillow
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    $9,008,600
    2% more+ $180K
    With Zillow Showcase(estimated)
    $9,188,772