About 16 East Trail
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.
Features of 16 East Trail
| MLS® # | 24168537 |
|---|---|
| Price | $7,950,000 |
| Bedrooms | 9 |
| Bathrooms | 7/3 |
| Full Baths | 7 |
| Half Baths | 3 |
| Square Footage | 8,188 |
| Acres | 2.89 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 16 East Trail |
|---|---|
| Area | Tokeneke |
| City | Darien |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06820 |
Amenities
| Parking | Detached Garage |
|---|---|
| Garage Spaces | 3 |
| Is Waterfront | No |
| Waterfront | Walk to Water, Beach Rights |
| Has Pool | Yes |
| Pool | Gunite, Heated, Salt Water, In Ground Pool |
Interior
| Interior Features | Auto Garage Door Opener, Security System |
|---|---|
| Appliances | Oven/Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer |
| Heating | Hot Air, Electric, Oil |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 5 |
Exterior
| Exterior | Shake, Clapboard |
|---|---|
| Exterior Features | Terrace, Lighting, Guest House, Patio, Grill, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler |
| Lot Description | Professionally Landscaped |
| Roof | Wood Shingle |
| Foundation | Concrete, Stone |
School Information
| Elementary | Tokeneke |
|---|---|
| Middle | Middlesex |
| High | Darien |
Additional Information
| Date Listed | April 20th, 2026 |
|---|---|
| Days on Market | 149 |
| Zoning | R-1 |
| RE / Bank Owned | No |
Listing Details
| Office | Compass Connecticut, LLC |
|---|