$8,495,000

16 East Trail, Darien, CT 06820

  • 9 beds |
  • 10 baths |
  • 8,188 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1908
  • Property Lot Size Icon2.89acre lot
  • Property Parking Icon 3 car garage
  • Property Price Per Square Feet Icon $1,037/sqft
  • Property List Date Icon Listed 2 months ago

Property 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.

Listing Status:
Active
Date Added:
April 20, 2026
Data Last Updated:
June 26, 2026 at 4:51PM
Listing Office:
Compass Connecticut, LLC : (203) 423-3100
Listing Agent:
Ashley Dineen : (203) 253-9616
MLS ID:
24168537
  • General: Auto Garage Door OpenerSecurity System
  • Rooms: Exercise RoomFoyerLaundry RoomMud RoomSolarium
  • Appliances: Oven/RangeWall OvenRange HoodRefrigeratorDishwasherWasherDryer
  • Laundry: Lower Level
  • Basement: FullPartially FinishedFull With Walk-Out
  • A/C: Central Air
  • Heating: Hot AirElectricOil
  • Fireplace: Fireplaces: 5
  • General: TerraceLightingGuest HousePatioGrillFruit TreesGarden AreaStone WallUnderground Sprinkler
  • Style: Colonial
  • Pool: GuniteHeatedSalt WaterIn Ground Pool
  • Roofing: Wood Shingle
  • HOA Amenities: Security ServiceSnow RemovalRoad Maintenance2200.0Annually
  • County: Fairfield
  • Zoning: R-1108948
  • Water: Public Water Connected
  • Sewer: Septic
  • Exclusions: See Listing agent for exclusion sheet

This listing courtesy of Ashley Dineen , Compass Connecticut, LLC

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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