16 East Trail
Darien, CT 06820
Tokeneke
9 Beds
8.5 Baths
8,188 sqft (on 2.89 acres)
9 Beds
8.5 Baths
8,188 sqft
(on 2.89 acres)
Local Information
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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.
Home Highlights
Parking
Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
$183/Monthly
Price/Sqft
$1,099
Listed
17 days ago
Home Details for 16 East Trail
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Interior Details Basement: Full,Partially FinishedNumber of Rooms: 21Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Rec Play Room, Study, Sun Room |
Beds & Baths Number of Bedrooms: 9Number of Bathrooms: 10Number of Bathrooms (full): 7Number of Bathrooms (half): 3 |
Dimensions and Layout Living Area: 8188 Square Feet |
Appliances & Utilities Appliances: Oven/Range, Oven, Range Hood, Refrigerator, Dishwasher, Washer, DryerDishwasherDryerLaundry: Lower Level,Mud RoomRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Electric,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 5Has a Fireplace |
Security Security: Security System |
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Exterior Home Features Roof: WoodPatio / Porch: Terrace, PatioOther Structures: Guest HouseExterior: Lighting, Outdoor Grill, Fruit Trees, Garden, Stone Wall, Underground SprinklerFoundation: Concrete Perimeter, StoneGardenHas a Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Detached,Garage Door Opener |
Pool Pool: Gunite, Heated, Salt Water, In GroundPool |
Frontage Waterfront: Walk to Water, Beach AccessNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 8188 Square Feet |
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Days on Market: 17 |
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Year Built Year Built: 1908 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Shake Siding, ClapboardNot a New ConstructionDoes Not Include Home Warranty |
Property Information Not Included in Sale: See Listing agent for exclusion sheetParcel Number: 108948 |
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Price List Price: $8,995,000Price Per Sqft: $1,099 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: DarienCommunity: Tokeneke |
School Information Elementary School: TokenekeJr High / Middle School: MiddlesexHigh School: Darien |
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Listing Agent Listing ID: 24168537 |
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Building Area Building Area: 8188 Square Feet |
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HOA Fee Includes: Security, Snow Removal, Road MaintenanceHas an HOAHOA Fee: $2,200/Annually |
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Lot Area: 2.89 Acres |
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BasementMls Number: 24168537Attic: Partially Finished, Walk-upAttribution Contact: (203) 253-9616Above Grade Unfinished Area: 8188Activation Date: Wed Apr 22 2026 |
Last check for updates: about 2 hours ago
Listing courtesy of Ashley Dineen, (203) 253-9616
Compass Connecticut, LLC, (203) 253-9616
Source: Smart MLS, MLS#24168537
Also Listed on Smart MLS.
Price History for 16 East Trail
| Date | Price | Event | Source |
|---|---|---|---|
| 04/22/2026 | $8,995,000 | Listed For Sale | Smart MLS #24168537 |
| 01/15/2010 | $5,275,000 | Sold | Smart MLS #98418423 |
| 05/20/2002 | $5,250,000 | Sold | Smart MLS #98127055 |
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Comparable Sales for 16 East Trail
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.29 | Single-Family Home | $6,800,000 | 06/06/25 | 6 | 7.5 | 9,872 | |
0.36 | Single-Family Home | $4,250,000 | 06/06/25 | 5 | 6 | 8,239 | |
0.42 | Single-Family Home | $6,500,000 | 04/20/26 | 6 | 7 | 6,959 | |
0.12 | Single-Family Home | $3,725,000 | 08/01/25 | 5 | 3.5 | 5,265 | |
0.47 | Single-Family Home | $6,500,000 | 06/24/25 | 5 | 6.5 | 6,474 | |
0.51 | Single-Family Home | $4,350,000 | 05/19/25 | 6 | 8.5 | 7,500 | |
0.28 | Single-Family Home | $3,750,000 | 08/11/25 | 5 | 5 | 4,358 | |
0.48 | Single-Family Home | $4,350,000 | 05/04/26 | 5 | 5 | 6,517 | |
0.26 | Single-Family Home | $3,205,000 | 03/27/26 | 4 | 3.5 | 3,972 | |
0.34 | Single-Family Home | $3,650,000 | 06/23/25 | 5 | 3.5 | 3,659 |
Assigned Schools
These are the assigned schools for 16 East Trail.
- Darien High School
- 9-12
- Public
- 1415 Students
10/10GreatSchools RatingParent Rating AverageExcellent in every respect. Rich choice of activities and academics. Experienced counselors and teachers and positive atmosphere. Strong support for IEP and 509.Parent Review6y ago - Middlesex Middle School
- 6-8
- Public
- 1068 Students
9/10GreatSchools RatingParent Rating AverageBullying at Middlesex is rampant and the administration goes out of their way to ignore the issue and place kids with bullies without taking corrective action.Parent Review2y ago - Tokeneke Elementary School
- PK-5
- Public
- 447 Students
8/10GreatSchools RatingParent Rating AverageThis school is rapidly going imploding with their horrible response to the COVID virus. Their remote schooling was implemented poorly for 2020-2021 and they actively tried to embarrass and ridicule the remote learners by facing the camera and tv on the other children so that they were on display for the class to see as some strange kid.During the recent BOE meeting for 2021-2022 school year, I was horrified. Every parent that spoke was fiercely against the state's mask mandate and it was clear as day the pressure they were putting on the district's physician to permit a local option that would not require masks.Darien is a horrible city in that it is filled with horrible people that not only support the right-wing fascist movement in the US and wear it with a badge of honor.Ask yourself, would you want your child being taught in a school that rejects science?Parent Review4y ago 
Check out schools near 16 East Trail.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Ashley Dineen, Compass Connecticut, LLC, (203) 253-9616
Agent Phone: (203) 253-9616
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