16 East Trail, Darien, CT 06820
Single Family For Sale
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About This Home
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 (203) 253-9616 with Compass Connecticut, LLC (203) 423-3100
Listing Snapshot
| Price | $8,495,000 | Days on Our Site | 57 days |
| Property Tax | $61,105/yr | Style | Colonial |
| Year Built | 1908 | Total Sq Ft | 8,188 |
| Lot Size | 2.89 acres | HOA Fees | $2,200/yr |
| Bedrooms | 9 | Full Bathrooms | 7 |
| Total Rooms | 21 | Half Baths | 3 |
Key Features
- Auto Garage Door Opener
- Security System
- Oven/Range
- Wall Oven
- Range Hood
- Refrigerator
- Dishwasher
- Washer
- Dryer
- Terrace
- Lighting
- Guest House
- Patio
- Grill
- Fruit Trees
- Garden Area
- Stone Wall
- Underground Sprinkler
- Gunite
- Heated
- Salt Water
- In Ground Pool
Structure & Parking
Systems & Utilities
Schools
Mortgage Calculator
Estimate only. Contact a lender for accurate figures.
Listing History
| Date | Event | Price |
|---|---|---|
| May 21, 2026 | Price Reduced | $8,495,000 |
| Apr 20, 2026 | Listed | $8,995,000 |
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Listing Agent
Ashley Dineen · (203) 253-9616
Compass Connecticut, LLC · (203) 423-3100
MLS# 24168537 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Jun 8, 2026 7:22 PM UTC
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16 East Trail, Darien CT, 06820
$8,495,000 • Active
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