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For sale
    • Price cut: $500K (5/21)
    $8,495,000

    16 East Trail, Darien, CT 06820

    9beds
    8,188sqft
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    Single Family Residence
    Built in 1908
    2.89 Acres Lot
    $-- Zestimate®
    $1,037/sqft
    $183/mo HOA

    What's special

    Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplaces that add warmth and character across its gracious living spaces. A classic carriage house offers a fully equipped 2-bedroom, 1-bath guest residence with its own kitchen, providing exceptional flexibility-ideal for extended stays, in-law living, or a private home office retreat. The grounds, designed by renowned landscape architect Janice Parker, are a true highlight-lush, structured, and beautifully layered for year-round interest. An in-ground saltwater pool completes the estate-like setting, creating a private retreat perfect for both entertaining and quiet enjoyment. Rich in history and elevated by a world-class design team, 16 East Trail offers a rare opportunity to own a piece of Darien's architectural legacy-seamlessly tailored for modern living.
    84 days
    |
    2,125
    |
    92
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    The Legacy Team at Compass,

    Ashley Dineen (203)253-9616,

    Compass Connecticut, LLC 203-423-3100

    Source: Smart MLS,MLS#: 24168537MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 9
      • Bathrooms: 10
      • Full bathrooms: 7
      • 1/2 bathrooms: 3
      Rooms
      • Room types: Exercise Room, Laundry, Solarium
      Primary bedroom
      • Features: Fireplace, Full Bath, Walk-In Closet(s)
      • Level: Upper
      • Area: 360 Square Feet
      • Dimensions: 20 x 18
      Bedroom
      • Features: Full Bath
      • Level: Upper
      • Area: 256 Square Feet
      • Dimensions: 16 x 16
      Bedroom
      • Level: Upper
      • Area: 168 Square Feet
      • Dimensions: 14 x 12
      Bedroom
      • Level: Upper
      • Area: 168 Square Feet
      • Dimensions: 14 x 12
      Bedroom
      • Level: Upper
      • Area: 154 Square Feet
      • Dimensions: 14 x 11
      Bedroom
      • Level: Upper
      • Area: 285 Square Feet
      • Dimensions: 19 x 15
      Bedroom
      • Features: Built-in Features, Full Bath
      • Level: Other
      • Area: 336 Square Feet
      • Dimensions: 16 x 21
      Bedroom
      • Level: Other
      • Area: 140 Square Feet
      • Dimensions: 14 x 10
      Bedroom
      • Level: Other
      • Area: 168 Square Feet
      • Dimensions: 14 x 12
      Dining room
      • Features: Built-in Features, Fireplace
      • Level: Main
      • Area: 323 Square Feet
      • Dimensions: 17 x 19
      Family room
      • Features: Bookcases, Built-in Features, Fireplace, Half Bath
      • Level: Main
      • Area: 630 Square Feet
      • Dimensions: 35 x 18
      Kitchen
      • Features: Remodeled
      • Level: Main
      • Area: 396 Square Feet
      • Dimensions: 18 x 22
      Living room
      • Features: Fireplace, Hardwood Floor
      • Level: Main
      • Area: 630 Square Feet
      • Dimensions: 35 x 18
      Rec play room
      • Level: Other
      • Area: 352 Square Feet
      • Dimensions: 16 x 22
      Study
      • Features: Bookcases, Built-in Features, Fireplace
      • Level: Main
      • Area: 156 Square Feet
      • Dimensions: 12 x 13
      Sun room
      • Level: Main
      • Area: 182 Square Feet
      • Dimensions: 13 x 14
      Heating
      • Forced Air, Electric, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Oven/Range, Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
      • Laundry: Lower Level, Mud Room
      Features
      • Entrance Foyer
      • Basement: Full,Partially Finished
      • Attic: Partially Finished,Walk-up
      • Number of fireplaces: 5
      Interior area
      • Total structure area: 8,188
      • Total interior livable area: 8,188 sqft
      • Finished area above ground: 8,188

      Property

      Parking
      • Total spaces: 3
      • Parking features: Detached, Garage Door Opener
      • Garage spaces: 3
      Features
      • Patio & porch: Terrace, Patio
      • Exterior features: Lighting, Outdoor Grill, Fruit Trees, Garden, Stone Wall, Underground Sprinkler
      • Has private pool: Yes
      • Pool features: Gunite, Heated, Salt Water, In Ground
      • Waterfront features: Walk to Water, Beach Access
      Lot
      • Size: 2.89 Acres
      • Features: Landscaped
      Details
      • Additional structures: Guest House
      • Parcel number: 108948
      • Zoning: R-1

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Shake Siding, Clapboard
      • Foundation: Concrete Perimeter, Stone
      • Roof: Wood
      Condition
      • New construction: No
      • Year built: 1908

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public

      Community & HOA

      Community
      • Security: Security System
      • Subdivision: Tokeneke
      HOA
      • Has HOA: Yes
      • Services included: Security, Snow Removal, Road Maintenance
      • HOA fee: $2,200 annually
      Location
      • Region: Darien

      Financial & listing details

      • Price per square foot: $1,037/sqft
      • Tax assessed value: $3,947,370
      • Annual tax amount: $61,105
      • Date on market: 4/20/2026
      • Exclusions: See Listing agent for exclusion sheet

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/21/2026Price change$8,495,000-5.6%$1,037/sqft
        Source: Smart MLS #24168537 Report a problem
        4/22/2026Listed for sale$8,995,000+38.5%$1,099/sqft
        Source: Smart MLS #24168537 Report a problem
        10/1/2019Listing removed$6,495,000$793/sqft
        Source: Halstead Real Estate #170127622 Report a problem
        9/27/2018Listed for sale$6,495,000+23.1%$793/sqft
        Source: Halstead Real Estate #170127622 Report a problem
        1/15/2010Sold$5,275,000-12%$644/sqft
        Source: Smart MLS #98418423 Report a problem
        5/2/2009Listed for sale$5,995,000-1.7%$732/sqft
        Source: William Pitt Sothebys International Realty #NON-MLS Report a problem
        6/29/2007Sold$6,100,000+16.2%$745/sqft
        Source: Smart MLS #98314616 Report a problem
        5/20/2002Sold$5,250,000+200%$641/sqft
        Source: Smart MLS #98127055 Report a problem
        6/30/1997Sold$1,750,000+32.1%$214/sqft
        Source: Public Record Report a problem
        6/2/1987Sold$1,325,000$162/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$61,105 +5.4%$3,947,370
        2024$57,987 +7.3%$3,947,370 +28.6%
        2023$54,048 +2.2%$3,069,150
        2022$52,881 +2.3%$3,069,150
        2021$51,684 +2.9%$3,069,150
        2020$50,211 -0.7%$3,069,150
        2019$50,549 -3.3%$3,069,150 -5.6%
        2018$52,254 -0.5%$3,249,610
        2017$52,514 +2.5%$3,249,610
        2016$51,246 +2.7%$3,249,610
        2015$49,882 +2.3%$3,249,610
        2014$48,777 -2.6%$3,249,610 -14.5%
        2013$50,067 +3.9%$3,801,630
        2012$48,205 +3.9%$3,801,630
        2011$46,380 +12.4%$3,801,630 +8.2%
        2010$41,245 -7.1%$3,513,230 -10%
        2009$44,403 -3.1%$3,905,300 +24.1%
        2008$45,805 +4.9%$3,148,110
        2007$43,664 +3.5%$3,148,110
        2006$42,185 -28%$3,148,110 -30%
        2005$58,555 +55.6%$4,497,300 +42.9%
        2004$37,620 +66.1%$3,148,110 +81.5%
        2003$22,649 -6.8%$1,734,250
        2001$24,314 +7.4%$1,734,250 -30%
        2000$22,649 +33.4%$2,477,500 +158.5%
        1999$16,983 $958,405
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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: Tokeneke

        Getting around

        34 / 100
        Car-Dependent
        38 / 100
        Some Transit
        31 / 100
        Somewhat Bikeable

        Nearby schools

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

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

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