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$8,995,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 7 Full Baths
  • 3 Partial Baths
  • 8,188 Sq. Ft.
  • 3 Car Garage
  • Updated 3 hours ago
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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.

Full Property Details for 16 E Trail

General

  • Price: $8,995,000
  • HOA FEE: $183/month
  • HOA FEE FREQ.: Annually
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24168537
  • Updated: Today (4/22/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 21
  • Rooms/Areas: Exercise Room, Foyer, Laundry Room, Mud Room, Solarium
  • Interior Features: Auto Garage Door Opener, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 5
  • Appliances: Oven/Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 10
  • Full Bathrooms: 7
  • Half Bathrooms: 3

Bedrooms

  • Total Bedrooms: 9
  • Primary Suite: Fireplace, Full Bath, Walk-In Closet, 18 x 20, Upper
  • Bedroom 1: Bedroom, 10 x 14, Other
  • Bedroom 2: Bedroom, 12 x 14, Other
  • Bedroom 3: Bedroom - Built-Ins, Full Bath, 21 x 16, Other
  • Bedroom 4: Bedroom, 11 x 14, Upper
  • Bedroom 5: Bedroom, 12 x 14, Upper
  • Bedroom 6: Bedroom, 12 x 14, Upper
  • Bedroom 7: Bedroom, 15 x 19, Upper
  • Bedroom 8: Bedroom - Full Bath, 16 x 16, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 18 x 35, Main
  • Family Room: Family Room - Book Shelves, Built-Ins, Fireplace, Half Bath, 18 x 35, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, 22 x 18, Main
  • Formal Dining Room: Formal Dining Room - Built-Ins, Fireplace, 19 x 17, Main
  • Study: Book Shelves, Built-Ins, Fireplace, 13 x 12, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, 22 x 16, Other
  • Rec Room: 22 x 16, Other
  • Laundry: Lower Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Salt Water, In Ground Pool

Exterior

  • Exterior Features: Terrace, Lighting, Guest House, Patio, Grill, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking: Detached Garage

Location

  • County: Fairfield
  • Neighborhood: Tokeneke
  • Driving Directions: Old Farm Rd to East Trail

School Information

  • Elementary School: Tokeneke
  • Middle School: Middlesex
  • High School: Darien

Community

  • Community Name: Tokeneke
  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Security Service, Snow Removal, Road Maintenance

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Electric, Oil
  • Heating Fuel: Electric, Oil
  • Water Heater: Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Shake, Clapboard
  • Basement Desc.: Full, Partially Finished, Full With Walk-Out
  • Roof: Wood Shingle
  • Attic: Yes
  • Square Feet: 8,188
  • Above Ground: 8,188 Sq. Ft.
  • Year Built: 1908

Lot Features

  • Lot Size (Acres): 2.89
  • Zoning: R-1
  • Lot Description: Professionally Landscaped

Water Features

  • Water Front Desc.: Walk to Water, Beach Rights

Financial Considerations

  • Association Fee: $2,200
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $3,947,370
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: See Listing agent for exclusion sheet
  • Property ID: 108948

Listed by Compass Connecticut, LLC, The Legacy Team at Compass, Ashley Dineen

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Listing agent

— 16 E Trail —

  • Ashley Dineen

    Compass Connecticut, LLC

Agent Contact: (203) 253-9616 Office Contact: (203) 423-3100

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 16 E Trail

School District:Darien School District
NameGradesDistance
Tokeneke Elementary School
7 Old Farm Road, Darien, CT 06820
K-50.2 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-82 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-121.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 16 E Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/22/2026
Listed
$8,995,000
70.52%
MLS
1/15/2010
Sold
$5,275,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 16 E Trail

Year
Property Taxes
Change
Tax Assessment
Change
2025
$61,105
5%
$3,947,370
—
2023
$57,987
7%
$3,947,370
29%
2023
$54,048
2%
$3,069,150
—
2022
$52,881
2%
$3,069,150
—
2021
$51,684
3%
$3,069,150
—
2020
$50,119
-1%
$3,069,150
—
2019
$50,549
-3%
$3,069,150
-6%
2018
$52,254
—
$3,249,610
—
2017
$52,514
2%
$3,249,610
—
2016
$51,246
3%
$3,249,610
—
2015
$49,882
2%
$3,249,610
—
2014
$48,777
-3%
$3,249,610
-15%
2012
$50,067
—
$3,801,630
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Compass Connecticut, LLC, The Legacy Team at Compass, Ashley Dineen

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16 East Trail, Darien, CT 06820 (MLS# 24168537) is a Single Family property with 9 bedrooms, 7 full bathrooms and 3 partial bathrooms. 16 East Trail is currently listed for $8,995,000 and was received on April 22, 2026. Want to learn more about 16 East Trail? Do you have questions about finding other Single Family real estate for sale in Tokeneke? You can browse all Tokeneke real estate or contact a Coldwell Banker agent to request more information.

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