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.
For sale
$8,495,000
16 East Trail, Darien, CT 06820
9beds
8,188sqft
Single Family Residence
Built in 1908
2.89 Acres Lot
$-- Zestimate®
$1,037/sqft
$217/mo HOA
What's special
- 132 days
- 2,127
- 94
Zillow last checked:
Listing updated:
Listed by:
The Legacy Team at Compass,
Ashley Dineen (203)253-9616,
Compass Connecticut, LLC 203-423-3100
Source: Smart MLS,MLS#: 24168537
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 10
- Full bathrooms: 7
- 1/2 bathrooms: 3
Rooms
- Room types: Exercise Room, Laundry, Solarium
Primary bedroom
- Features: Fireplace, Full Bath, Walk-In Closet(s)
- Level: Upper
- Area: 360 Square Feet
- Dimensions: 20 x 18
Bedroom
- Features: Full Bath
- Level: Upper
- Area: 256 Square Feet
- Dimensions: 16 x 16
Bedroom
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 14 x 12
Bedroom
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 14 x 12
Bedroom
- Level: Upper
- Area: 154 Square Feet
- Dimensions: 14 x 11
Bedroom
- Level: Upper
- Area: 285 Square Feet
- Dimensions: 19 x 15
Bedroom
- Features: Built-in Features, Full Bath
- Level: Other
- Area: 336 Square Feet
- Dimensions: 16 x 21
Bedroom
- Level: Other
- Area: 140 Square Feet
- Dimensions: 14 x 10
Bedroom
- Level: Other
- Area: 168 Square Feet
- Dimensions: 14 x 12
Dining room
- Features: Built-in Features, Fireplace
- Level: Main
- Area: 323 Square Feet
- Dimensions: 17 x 19
Family room
- Features: Bookcases, Built-in Features, Fireplace, Half Bath
- Level: Main
- Area: 630 Square Feet
- Dimensions: 35 x 18
Kitchen
- Features: Remodeled
- Level: Main
- Area: 396 Square Feet
- Dimensions: 18 x 22
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 630 Square Feet
- Dimensions: 35 x 18
Rec play room
- Level: Other
- Area: 352 Square Feet
- Dimensions: 16 x 22
Study
- Features: Bookcases, Built-in Features, Fireplace
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 x 13
Sun room
- Level: Main
- Area: 182 Square Feet
- Dimensions: 13 x 14
Heating
- Forced Air, Electric, Oil
Cooling
- Central Air
Appliances
- Included: Oven/Range, Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
- Laundry: Lower Level, Mud Room
Features
- Entrance Foyer
- Basement: Full,Partially Finished
- Attic: Partially Finished,Walk-up
- Number of fireplaces: 5
Interior area
- Total structure area: 8,188
- Total interior livable area: 8,188 sqft
- Finished area above ground: 8,188
Property
Parking
- Total spaces: 3
- Parking features: Detached, Garage Door Opener
- Garage spaces: 3
Features
- Patio & porch: Terrace, Patio
- Exterior features: Lighting, Outdoor Grill, Fruit Trees, Garden, Stone Wall, Underground Sprinkler
- Has private pool: Yes
- Pool features: Gunite, Heated, Salt Water, In Ground
- Waterfront features: Walk to Water, Beach Access
Lot
- Size: 2.89 Acres
- Features: Landscaped
Details
- Additional structures: Guest House
- Parcel number: 108948
- Zoning: R-1
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Shake Siding, Clapboard
- Foundation: Concrete Perimeter, Stone
- Roof: Wood
Condition
- New construction: No
- Year built: 1908
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & HOA
Community
- Security: Security System
- Subdivision: Tokeneke
HOA
- Has HOA: Yes
- Services included: Security, Snow Removal, Road Maintenance
- HOA fee: $2,600 annually
Location
- Region: Darien
Financial & listing details
- Price per square foot: $1,037/sqft
- Tax assessed value: $3,947,370
- Annual tax amount: $61,105
- Date on market: 4/20/2026
- Exclusions: See Listing agent for exclusion sheet
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/21/2026 | Price change | $8,495,000-5.6%$1,037/sqft |
Source:  Smart MLS #24168537 Report a problem | ||
| 4/22/2026 | Listed for sale | $8,995,000+38.5%$1,099/sqft |
Source: Smart MLS #24168537 Report a problem | ||
| 10/1/2019 | Listing removed | $6,495,000$793/sqft |
Source: Halstead Real Estate #170127622 Report a problem | ||
| 9/27/2018 | Listed for sale | $6,495,000+23.1%$793/sqft |
Source: Halstead Real Estate #170127622 Report a problem | ||
| 1/15/2010 | Sold | $5,275,000-12%$644/sqft |
Source: Smart MLS #98418423 Report a problem | ||
| 5/2/2009 | Listed for sale | $5,995,000-1.7%$732/sqft |
Source: William Pitt Sothebys International Realty #NON-MLS Report a problem | ||
| 6/29/2007 | Sold | $6,100,000+16.2%$745/sqft |
Source: Smart MLS #98314616 Report a problem | ||
| 5/20/2002 | Sold | $5,250,000+200%$641/sqft |
Source: Smart MLS #98127055 Report a problem | ||
| 6/30/1997 | Sold | $1,750,000+32.1%$214/sqft |
Source: Public Record Report a problem | ||
| 6/2/1987 | Sold | $1,325,000$162/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $61,105 +5.4% | $3,947,370 |
| 2024 | $57,987 +7.3% | $3,947,370 +28.6% |
| 2023 | $54,048 +2.2% | $3,069,150 |
| 2022 | $52,881 +2.3% | $3,069,150 |
| 2021 | $51,684 +2.9% | $3,069,150 |
| 2020 | $50,211 -0.7% | $3,069,150 |
| 2019 | $50,549 -3.3% | $3,069,150 -5.6% |
| 2018 | $52,254 -0.5% | $3,249,610 |
| 2017 | $52,514 +2.5% | $3,249,610 |
| 2016 | $51,246 +2.7% | $3,249,610 |
| 2015 | $49,882 +2.3% | $3,249,610 |
| 2014 | $48,777 -2.6% | $3,249,610 -14.5% |
| 2013 | $50,067 +3.9% | $3,801,630 |
| 2012 | $48,205 +3.9% | $3,801,630 |
| 2011 | $46,380 +12.4% | $3,801,630 +8.2% |
| 2010 | $41,245 -7.1% | $3,513,230 -10% |
| 2009 | $44,403 -3.1% | $3,905,300 +24.1% |
| 2008 | $45,805 +4.9% | $3,148,110 |
| 2007 | $43,664 +3.5% | $3,148,110 |
| 2006 | $42,185 -28% | $3,148,110 -30% |
| 2005 | $58,555 +55.6% | $4,497,300 +42.9% |
| 2004 | $37,620 +66.1% | $3,148,110 +81.5% |
| 2003 | $22,649 -6.8% | $1,734,250 |
| 2001 | $24,314 +7.4% | $1,734,250 -30% |
| 2000 | $22,649 +33.4% | $2,477,500 +158.5% |
| 1999 | $16,983 | $958,405 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: Tokeneke
Nearby schools
Schools provided by the listing agent
- Elementary: Tokeneke
- Middle: Middlesex
- High: Darien
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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