16 East Trail Darien, CT 06820
Darien AreaEstimated payment $51,427/month
Highlights
- Detached Guest House
- Heated In Ground Pool
- Colonial Architecture
- Tokeneke Elementary School Rated A+
- 2.89 Acre Lot
- Fruit Trees
About This Home
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.
Listing Agent
Compass Connecticut, LLC Brokerage Phone: (203) 253-9616 License #RES.0761034 Listed on: 04/20/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $61,105
Year Built
- Built in 1908
Lot Details
- 2.89 Acre Lot
- Stone Wall
- Sprinkler System
- Fruit Trees
- Garden
HOA Fees
- $183 Monthly HOA Fees
Home Design
- Colonial Architecture
- Concrete Foundation
- Stone Foundation
- Frame Construction
- Wood Shingle Roof
- Clap Board Siding
- Shake Siding
Interior Spaces
- 8,188 Sq Ft Home
- 5 Fireplaces
- Mud Room
- Entrance Foyer
- Solarium
- Home Gym
- Home Security System
Kitchen
- Built-In Oven
- Range Hood
- Dishwasher
Bedrooms and Bathrooms
- 9 Bedrooms
Laundry
- Laundry Room
- Laundry on lower level
- Dryer
- Washer
Attic
- Walkup Attic
- Partially Finished Attic
Partially Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
Parking
- 3 Car Garage
- Automatic Garage Door Opener
Pool
- Heated In Ground Pool
- Gunite Pool
- Saltwater Pool
Outdoor Features
- Patio
- Terrace
- Exterior Lighting
- Outdoor Grill
Additional Homes
- Detached Guest House
Schools
- Tokeneke Elementary School
- Middlesex School
- Darien High School
Utilities
- Central Air
- Heating System Uses Oil
Community Details
- Association fees include security service, snow removal, road maintenance
Listing and Financial Details
- Exclusions: See Listing agent for exclusion sheet
- Assessor Parcel Number 108948
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $61,105 | $3,947,370 | $1,850,310 | $2,097,060 |
| 2024 | $57,987 | $3,947,370 | $1,850,310 | $2,097,060 |
| 2023 | $54,048 | $3,069,150 | $1,370,600 | $1,698,550 |
| 2022 | $52,881 | $3,069,150 | $1,370,600 | $1,698,550 |
| 2021 | $51,684 | $3,069,150 | $1,370,600 | $1,698,550 |
| 2020 | $50,211 | $3,069,150 | $1,370,600 | $1,698,550 |
| 2019 | $50,549 | $3,069,150 | $1,370,600 | $1,698,550 |
| 2018 | $52,254 | $3,249,610 | $1,370,600 | $1,879,010 |
| 2017 | $52,514 | $3,249,610 | $1,370,600 | $1,879,010 |
| 2016 | $51,246 | $3,249,610 | $1,370,600 | $1,879,010 |
| 2015 | $49,882 | $3,249,610 | $1,370,600 | $1,879,010 |
| 2014 | $48,777 | $3,249,610 | $1,370,600 | $1,879,010 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 05/21/2026 05/21/26 | Price Changed | $8,495,000 | -5.6% | $1,037 / Sq Ft |
| 04/22/2026 04/22/26 | For Sale | $8,995,000 | -- | $1,099 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $5,275,000 | -- | |
| Warranty Deed | $6,100,000 | -- | |
| Warranty Deed | $5,250,000 | -- | |
| Warranty Deed | $1,750,000 | -- | |
| Deed | $1,325,000 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $500,000 | No Value Available | |
| Previous Owner | $285,000 | No Value Available | |
| Previous Owner | $2,000,000 | No Value Available | |
| Previous Owner | $929,000 | No Value Available |
Source: SmartMLS
MLS Number: 24168537
APN: DARI-000065-000000-000052
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
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