1. Connecticut
  2. Darien
  3. 17 Contentment Island Road
$10,895,000

17 Contentment Island Road, Darien, CT 06820

  • 6 beds |
  • 5 baths |
  • 7,174 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1909
  • Property Lot Size Icon2.45acre lot
  • Property Parking Icon 3 car garage
  • Property Price Per Square Feet Icon $1,519/sqft
  • Property List Date Icon Listed 11 days ago

Property Description

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.

Listing Status:
Active
Date Added:
September 2, 2025 at 05:35PM
Listing Office:
Houlihan Lawrence : (203) 655-8238
Listing Agent:
Douglas Milne : (203) 667-0344
MLS ID:
24115997
  • General: Auto Garage Door OpenerSecurity System
  • Appliances: Gas CooktopGas RangeOven/RangeRange HoodRefrigeratorDishwasherWasherElectric Dryer
  • Laundry: Upper Level
  • Basement: PartialUnfinishedInterior AccessPartial With HatchwayConcrete Floor
  • A/C: Window Unit
  • Heating: Hot WaterOil
  • Fireplace: Fireplaces: 4

This listing courtesy of Douglas Milne, Houlihan Lawrence

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

T

Tokeneke Elementary School

7 Old Farm Rd, Darien, CT, 06820

Grades KG-5

1.12 miles away

M

Middlesex Middle School

204 Hollow Tree Ridge Rd, Darien, CT, 06820

Grades 6-8

2.49 miles away

D

Darien High School

80 High School Ln, Darien, CT, 06820

Grades 9-12

2.71 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.