16 East Trail, TokenekeDarien, CT 06820MLS Number 24168537

  • Price: $8,995,000
  • Est. Mortgage of $/month
  • 25 Days on Market
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Federal 30-year interest rate: 6.37% last updated on May 7, 2026
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  • 9Bedrooms
  • 2.89Acreage
  • 10Bathrooms
  • 1908Year Built

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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.
Listed by Ashley Dineen of Compass Connecticut,LLC ((203) 253-9616)

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More Info

Basic Information

  • MLS Number24168537
  • StatusACT
  • List Price$8,995,000
  • Square Feet8,188
  • Property TypeSingle Family For Sale
  • HoaYes
  • Hoa fee amount2200
  • Hoa fee frequencyAnnually
  • List TeamThe Legacy Team at Compass

Property

  • Acreage2.89
  • Lot DescriptionProfessionally Landscaped
  • Parking Spaces
  • SwimmingpoolYes
  • Pool descriptionGunite, Heated, Salt Water, In Ground Pool

Utilities

  • Waters ourcePublic Water Connected
  • Cooling SystemCentral Air
  • Hot water descriptionTank Size Unknown
  • Heating FuelElectric, Oil
  • Fuel tank locationAbove Ground
  • Heat SystemHot Air
  • Sewage systemSeptic

Tax Information

  • Assessed value$3,947,370
  • Milrate total15
  • Tax YearJuly 2025-June 2026
  • Taxes$61,105

Location

  • StateCT
  • Zip06820
  • CountyFairfield
  • NeighborhoodTokeneke
  • Middle Junior High SchoolMiddlesex

Interior

  • Rooms21
  • Rooms additionalExercise Room, Foyer, Laundry Room, Mud Room, Solarium
  • Interior featuresAuto Garage Door Opener, Security System
  • RoofWood Shingle

Exterior

  • Exterior features
    • Fruit Trees
    • Garden Area
    • Grill
    • Guest House
    • Lighting
    • Patio
    • Stone Wall
    • Terrace
    • Underground Sprinkler
  • Exterior sidingShake, Clapboard

Water Body

  • Waterfront DescriptionWalk to Water, Beach Rights

Other

  • Appliances Included
    • Dishwasher
    • Dryer
    • Oven/Range
    • Range Hood
    • Refrigerator
    • Wall Oven
    • Washer
  • Association fee includesSecurity Service, Snow Removal, Road Maintenance
  • Original listprice$8,995,000
  • ExclusionsSee Listing agent for exclusion sheet
  • Date Listed04/20/2026

School Information

  • Elementary SchoolTokeneke
  • High SchoolDarien

Rooms

  • Laundry room infoLower Level

Building

  • Full Bath7
  • Half Baths3
  • BasementFull, Partially Finished, Full With Walk-Out
  • Attic descriptionPartially Finished, Walk-up
  • AtticYes
  • Garage Spaces3
  • Bedrooms9
  • Bathroom10
  • Year Built1908
  • Property StyleColonial
  • Fireplaces5
  • FoundationConcrete, Stone
  • Garage Parking InfoDetached Garage
  • New construction typeNo/Resale
  • Inlaw apartmentyPossible

Amenities

  • Other AmenitiesBasement, Beachfront, Fireplace, Pool, Waterfront
Sotheby's International Realty | William Pitt
Sotheby's International Realty | William Pitt
Office: 203-796-7700
112 Federal Road
Danbury, CT 06811

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