New Listing - 04/20/2026
Listing courtesy of Ashley Dineen (203) 253-9616, Compass Connecticut, LLC (203) 423-3100
16 East Trail, Darien, (Tokeneke), CT, 06820
21 rooms
9 beds
7 Full / 3 Half baths
1908
Colonial
8,188 sqft
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.
Status:
Active
Town:
Darien
Type:
Single-family residential
Laundry Remarks:
Lower Level
Zoning:
R-1
Garage:
3-car Detached Garage
Heating:
Hot Air
Cooling:
Central Air
Basement:
Full, Partially Finished, Full With Walk-Out
Common Charge:
$2,200 Annually
Acreage:
2.89
Est. Taxes:
$61,105
Assessment
$3,947,370
HOA Fee
$2,200
Lot Description:
Professionally Landscaped
Elementary School:
Tokeneke
Middle School:
Middlesex
High School:
Darien
Days on Market:
5
Appliances:
Oven/Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Pool:
Gunite, Heated, Salt Water, In Ground Pool
MLS #:
24168537
Community Info
School Info
Walk Score
Mass Transit
Yelp
Copyright ©2026 SmartMLS, Inc.