Active Under Contract
Price CutPrice Drop: $545K (10/23)
Single family home for sale at 16 East Trl, Darien, CT 06820 | MLS# 24168537 | Listing updated on 2026-10-23
Photo 1 of Single family home for sale at 16 East Trl, Darien, CT 06820 | MLS# 24168537 | Listing updated on 2026-10-23
Photo 2 of Single family home for sale at 16 East Trl, Darien, CT 06820 | MLS# 24168537 | Listing updated on 2026-10-23
Photo 3 of Single family home for sale at 16 East Trl, Darien, CT 06820 | MLS# 24168537 | Listing updated on 2026-10-23
Photo 4 of Single family home for sale at 16 East Trl, Darien, CT 06820 | MLS# 24168537 | Listing updated on 2026-10-23
35+
Beds Icon

Street View

$7,950,000

Monthly Est:$39,570

  • Beds Icon9 Beds
  • Beds Icon
    10 Baths
  • Beds Icon8,188sqft

16 East Trl, Darien, CT 06820

$39,570/moEst:

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  • Single Family Residence

  • Built in 1908

  • $216.67/mo HOA

  • 2.89 acres lot

  • $971/sq.ft

Description

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.

  • Houzeo last checked: 2 minutes ago
  • Listing updated: October 23, 2026 at 9:50 pm
  • Listing Provided by: Ashley Dineen | Compass Connecticut, LLC
  • Source: SMART MLS-CT | MLS#: 24168537 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fairfield County

  • City

    Darien

  • Neighborhood

    --

  • Year Built

    1908

  • HOA Fees

    $216.67/mo

  • Finished Area

    8,188 sqft

  • Lot Size

    2.89 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24168537

  • MLS Status

    Under Contract

  • Days on Market

    193

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Location

HOA Management

1

HOA Fees

$2,600/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Snow Removal Snow Removal

Road Maintenance Road Maintenance

Security Service Security Service

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 9

    Bathrooms: 10

Interior

  • Appliances

    Oven/range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

  • Sewer

    Septic

  • Cooling

    Central Air

  • Heating

    Electric, Oil

  • Exterior Features

    Terrace, Lighting, Guest House, Patio, Grill, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler

  • Interior Features

    Auto Garage Door Opener, Security System

Construction

  • Year Built

    Year Built: 1908

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Foundation Details

    Concrete, Stone

  • Roof

    Wood Shingle

Utilities & Energy

  • Water Source

    Public Water Connected

  • Parking Features

    Detached Garage

  • Pool Features

    Gunite, Heated, Salt Water, In Ground Pool

  • Basement

    Full, Partially Finished, Full With Walk Out

  • Laundry Features

    Lower Level

Other Features

  • Subdivision Name

    Tokeneke

  • Lot Features

    Professionally Landscaped

Price History

DateEventPrice

09/01/2026

Source: mls_logoSMART MLS-CT #24168537

Contingent (Active Under Contract)

$7,950,000 -6.42%

$971/sqft

05/21/2026

Source: mls_logoSMART MLS-CT #24168537

Price Decreased

$8,495,000 -5.56%

$1,037/sqft

04/22/2026

Source: mls_logoSMART MLS-CT #24168537

Listed for Sale

$8,995,000

$1,099/sqft

04/20/2026

Source: mls_logoSMART MLS-CT #24168537

Coming Soon

$8,995,000 +70.52%

$1,099/sqft

01/18/2010

Source: #98418423

Sold

$5,275,000 +22834.78%

$644/sqft

Show more

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 31, 2026, 04:15AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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