Property photo 1
6 Beds
5 Baths
7,174 sqft

$9,420,000

17 Contentment Island Road, Darien CT, 06820

Price per sqft$1,313.07
Built in1909
Property size7,174 sqft
Property typeResidential

Overview

Sold

Closed

Listed Sep 2, 2025

Updated 3 weeks ago

Introducing one of Tokeneke's most iconic waterfront estates-available for the first time in 50 years. This rare and storied compound is set on 2.4 acres of exquisitely landscaped grounds with 180 feet of private shoreline along Long Island Sound. It offers an unrivaled blend of historic charm, timeless elegance, and breathtaking coastal beauty. A sweeping two-story paneled foyer leads to a gracious formal living and dining rooms with soaring ceilings, fireplaces, and uninterrupted views of the water. Sunlight pours into the sophisticated sunroom-an ideal setting for quiet mornings or refined entertaining. The expansive kitchen and breakfast area open seamlessly to a family room with a granite fireplace, while a discreet back stairway leads to a stunning double-height billiards room with vaulted, beamed ceilings. The second floor is anchored by a grand primary suite with an oversized waterfront balcony, offering a private vantage point for sunsets over the Sound. Two additional bedrooms complete this level, with three more on the top floor to accommodate family or guests in style. A separate three-car garage includes a fully finished upper level with a full bath-ideal for a guest suite, gym, or private office. This exceptional estate embodies the quiet prestige of a bygone era, offering privacy, beauty, and unparalleled access to the water-all in the heart of Darien's most coveted private enclave. A once-in-a-generation opportunity to own a true coastal masterpiece.

Additional information

MLS® ID
24115997

Interior Features

Bedrooms
6
Bathrooms
5
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
2.45 Acres

Other Property Details

Taxes
$109,003
Tax Frequency
Annually
Association Fee Frequency
Yearly
Garage
Yes
Waterfront
Yes
MLS provider logo

Listed by Douglas Milne with Houlihan Lawrence (203) 667-0344. Bought with Casey Lange of Compass Connecticut, LLC.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/25/2026. This information is for personal, non-commercial use only and may not be used for any purpose other than identifying properties the viewer may be interested in purchasing. MLS data is generally considered reliable but is not guaranteed accurate by the MLS. Buyers are responsible for verifying all information and should conduct their own investigation or consult a professional. Some MLS data may have been provided by sources other than the listing agent. Unless stated in writing, the Broker/Agent has not verified information obtained from outside sources. The Broker/Agent may or may not have been the listing and/or selling agent, and cannot guarantee the accuracy of any property location shown on a map. Any offer of compensation is made only to participants of the MLS where the listing is filed.

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Data last updated on 8/25/2026 at 3:58 AM UTC.

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