17 Contentment Island Road

Darien, CT 06820 Directions
$9,895,000
  • 6Bed
  • 4/1Baths
  • 7,174Sqft
  • 2.45Acres
  • $4,539HOA
  • 1909Built

Property Highlights

  • Elementary: Tokeneke
  • Jr. High School: Middlesex
  • High School: Per Board Of Ed
  • Neighborhood: Contentment Island
  • Price/Sqft: $1,379
  • Days on Market: 96
  • MLS: 24115997

Property Highlights

  • Elementary: Tokeneke
  • Jr. High School: Middlesex
  • High School: Per Board Of Ed
  • Neighborhood: Contentment Island
  • Price/Sqft: $1,379
  • Days on Market: 96
  • MLS: 24115997

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...

Property Highlights

  • Elementary: Tokeneke
  • Jr. High School: Middlesex
  • High School: Per Board Of Ed
  • Neighborhood: Contentment Island
  • Price/Sqft: $1,379
  • Days on Market: 96
  • MLS: 24115997

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.

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.

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  • Additional Information
    • Association Fee / Frequency: $4,539.00 / Annually
    • Attic Description: Unfinished, Floored, Pull-Down Stairs
    • Average Days On Market: 79
    • Basement Description: Partial, Unfinished, Interior Access, Partial With Hatchway, Concrete Floor
    • Days On Market: 96
    • Elementary School: Tokeneke
    • Garage: Detached Garage, Driveway
    • Garage Count: 3
    • HOA Fee: $4,539
    • HOA Includes: Security Service
    • High School: Per Board of Ed
    • Is Occupied?: Vacant
    • Is Waterfront?: Yes
    • Junior High School: Middlesex
    • Living Area SqFt: 7,174
    • Neighborhood: Contentment Island
    • Property Tax: $109,003
    • Sewer: Septic
    • Style: Colonial
    • Tax Amount: $109,003
    • Tax Year: July 2025-June 2026
    • Type: Single Family For Sale
    • Year Built: 1909
    • Year Built Details: Public Records
    • Zoning: R-1
  • Amenities
    • Security System
  • Interior/Exterior Features
    • Air Conditioning: Window Unit
    • Appliances Included: Gas Cooktop, Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer
    • Attic: Yes
    • Beds: 6
    • Cooling: Window Unit
    • Exterior Features: Balcony,Garden Area,Guest House,French Doors,Underground Sprinkler,Patio
    • Exterior Siding: Stone
    • Fireplaces: 4
    • Full Baths: 4
    • Furnace Type: Oil
    • Half Baths: 1
    • Heat: Oil
    • Heat Fuel: Oil
    • Hot Water: Oil, 50 Gallon Tank
    • Laundry Room: Upper Level
    • Roof: Slate
    • Rooms: 12
William Pitt / Julia B. Fee Sotheby's International Realty

Darien Brokerage

1057 Post Road
Darien, CT 06820

Listing Courtesy of Douglas Milne of Houlihan Lawrence.

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