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Request Info$8,495,000
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16 East Trail Overview
- Time on Site:
- 70 days
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.
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16 East Trail Facts & Features
- Type Single Family
- Sq. ft. 8,188
- Price/Sq.ft. $1,037
- Lot 2.89 Acres
Details
General
Association/HOA
- Association Fee: $2,200.00
- Association Fee Frequency: Annually
- Association Fee Includes: Security Service, Snow Removal, Road Maintenance
- Association: Yes
School Information
- Elementary School: Tokeneke
- Middle Or Junior School: Middlesex
- High School: Darien
Listing Information
- Bank Owned Property: No
- Potential Short Sale: No
Building Information
- Year Built: 1908
Location/Region
- County Or Parish: Fairfield
- Neighborhood: Tokeneke
Building Exterior/Construction
- New Construction Type: No/Resale
Tax Information
- Tax Annual Amount: $61,105.00
- Tax Year: July 2025-June 2026
General Information
- Exclusions: See Listing agent for exclusion sheet
- Parcel Number: 108948
- Property Type: Single Family For Sale
- Zoning: R-1
Interior
Parking Information
- Garage Spaces: 3
Beds/Baths
- Bathrooms Full: 7
- Bathrooms Half: 3
- Bathrooms Total: 10
- Bedrooms Total: 9
Building Interior
- Attic Description: Partially Finished, Walk-up
- Attic: Yes
- Fuel Tank Location: Above Ground
- Heat Fuel Type: Electric, Oil
- Hot Water Description: Tank Size Unknown
- In Law Apartment: Possible
- Laundry Room Info: Lower Level
- Rooms Additional: Exercise Room, Foyer, Laundry Room, Mud Room, Solarium
General Information
- Appliances: Oven/Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
- Basement: Full, Partially Finished, Full With Walk-Out
- Cooling: Central Air
- Fireplaces Total: 5
- Foundation Details: Concrete, Stone
- Heating: Hot Air
- Interior Features: Auto Garage Door Opener, Security System
- Living Area: 8188
Exterior
Parking Information
- Parking Features: Detached Garage
Lot Information
- Lot Features: Professionally Landscaped
- Lot Size Acres: 2.89
- Lot Size Source: Public Records
- Water Source: Public Water Connected
Waterfront/View
- Waterfront Features: Walk to Water, Beach Rights
- Waterfront: No
Building Exterior/Construction
- Architectural Style: Colonial
- Construction Materials: Shake, Clapboard
- Roof: Wood Shingle
General Information
- Exterior Features: Terrace, Lighting, Guest House, Patio, Grill, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler
- Pool Features: Gunite, Heated, Salt Water, In Ground Pool
- Pool Private: Yes
- Sewer: Septic
Room Information
Room: Eat-In Kitchen
- Level: Main
- Length: 22
- Width: 18
- Description: Remodeled
Room: Family Room
- Level: Main
- Length: 18
- Width: 35
- Description: Book Shelves,Built-Ins,Fireplace,Half Bath
Room: Formal Dining Room
- Level: Main
- Length: 19
- Width: 17
- Description: Built-Ins,Fireplace
Room: Living Room
- Level: Main
- Length: 18
- Width: 35
- Description: Fireplace,Hardwood Floor
Room: Study
- Level: Main
- Length: 13
- Width: 12
- Description: Book Shelves,Built-Ins,Fireplace
Room: Sun Room
- Level: Main
- Length: 14
- Width: 13
Room: Bedroom
- Level: Other
- Length: 10
- Width: 14
Room: Bedroom
- Level: Other
- Length: 12
- Width: 14
Room: Bedroom
- Level: Other
- Length: 21
- Width: 16
- Description: Built-Ins,Full Bath
Room: Rec/Play Room
- Level: Other
- Length: 22
- Width: 16
Room: Bedroom
- Level: Upper
- Length: 16
- Width: 16
- Description: Full Bath
Room: Bedroom
- Level: Upper
- Length: 11
- Width: 14
Room: Bedroom
- Level: Upper
- Length: 15
- Width: 19
Room: Bedroom
- Level: Upper
- Length: 12
- Width: 14
Room: Bedroom
- Level: Upper
- Length: 12
- Width: 14
Room: Primary BR Suite
- Level: Upper
- Length: 18
- Width: 20
- Description: Fireplace,Full Bath,Walk-In Closet
16 East Trail Monthly Cost
16 East Trail Market Data
Based on the last 30 days in this zip code
$4,422,954
Average List Price
$946
Average Price per Square Foot
32
Properties Sold
66
Average Days on Market
111
Properties for Sale
16 East Trail History
| Date | Value | Agent |
|---|---|---|
| 5/21/2026Source: Smart MLS | $8,495,000 -5.6% |
|
| 4/21/2026Source: Smart MLS | Active |
|
| 4/20/2026Source: Smart MLS | April 20, 2026 |
|
| 6/20/2022Source: Smart MLS | September 13, 2021 |
|
| 6/20/2022Source: Smart MLS | September 13, 2021 |
Listing provided courtesy of Compass Connecticut, LLC- MLS# 24168537
Contact Information: (203) 253-9616
Contact Information: (203) 253-9616