George Cress of Real Broker Email: george@cress.co (dot co) Call/Text: 212-203-5251
Darien, CT / 148 DAYS ON MARKET
16 East TrailDarien, CT 06820
Asking price$7,950,000ActiveReduced $1,045,000 (11.6%) from original price · Price history ↓
Open house
Our Take
16 East Trail combines a 1908 main residence in the Tokeneke Association with a classic carriage house. The main home offers seven bedrooms, six full baths, and five fireplaces. A renovation by architect Peter Pennoyer, interiors by Katie Ridder, and grounds designed by Janice Parker are part of the property’s documented history. The carriage house adds two bedrooms, one bath, and a kitchen. An in-ground saltwater pool completes the grounds.
At a glance
Active · MLS #24168537- Bedrooms
- 9
- BathroomsBaths
- 7 full / 3 half
- Square feet
- 8,188
- Year built
- 1908
- Acres
- 2.89
- Property taxes
- $61,105
July 2025-June 2026
What stands out
- 1908 residence in the Tokeneke Association
- Renovation by architect Peter Pennoyer
- Interiors by Katie Ridder
- Five fireplaces in the main residence
- Two-bedroom carriage house with kitchen
- Grounds designed by Janice Parker
- In-ground saltwater pool
Read the full listing 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.
Schools
- Elementary
- Tokeneke
- Middle
- Middlesex
- High
- Darien
Schools as reported by SmartMLS. Confirm attendance assignments with the district.
A closer look at the location
Open Google Maps ↗16 East Trail, Darien, CT 06820
Price history
| Date | Event | Price |
|---|---|---|
| Latest asking price | $7,950,000 | |
| Originally listed | $8,995,000 |
Intermediate price changes and previous listings may not be included.
Could this be your next home?
Let’s talk about the property—and what working with Cress could save you.
*Base estimate: $7,950,000 asking price × assumed 2.5% buyer-agent commission × 60% rebate = $119,250. For the $5M+ tier, we offer a 60% rebate or more; contact Cress to determine any additional rebate. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.
Listed by Compass Connecticut, LLC · (203) 423-3100
Ashley Dineen
SmartMLS · Listing #24168537 · Active
Listing data checked: Sep 17, 2026, 7:00 PM EDT.
Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.
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