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42 Contentment Island Road, Darien, CT 06820


  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 6,449 Sq. Ft.
  • 3 Car Garage
42 Contentment Island Road, Darien, CT 06820View this property at 42 Contentment Island Road, Darien, CT 06820
42 Contentment Island RoadDarienCT06820

Property Description

Sensational direct waterfront property located in the private Tokeneke Association. This magnificent Tudor home includes 3.2 secluded acres at the end of Contentment Island with extra lot potential. A dock and tennis court make this a perfect setting to enjoy outdoor activities on Scott's Cove and L.I. Sound. Built in 1900, the architectural integrity remains while updates have embraced its waterfront location and surrounding trees. Large picture windows, French doors, a seaside terrace and covered porch bring the outside in to this beloved home. Upstairs are 5 bedrooms, a family room and an office with a view all its own. Sea breezes fill the master suite with sitting room. A one-bedroom waterfront cottage is above the 3-car garage.

Full Property Details for 42 Contentment Island Road


  • Price: $9,850,000
  • HOA FEE: $3,677
  • Taxes: $78,202 (July 2017-June 2018)
  • Status: Active
  • Type: Single Family
  • MLS ID: 99157920
  • Updated: 2/5/2018
  • Added: 545 day(s) ago

Property History

  • 42 Contentment Island Road, Darien, CT
  • Reduced to $9,850,000 on 1/25/18
  • Listed at $11,200,000 on 8/24/16


  • Number of Rooms: 11
  • Appliances: Dishwasher, Disposal, Dryer, Oven/Range, Refrigerator, Wall Oven, Washer



  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2


  • Total Bedrooms: 6


  • Exterior Features: French Doors, Guest House, Gutters, Lighting, Patio, Underground Sprinkler, Tennis Court, Terrace
  • Color: natural


  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage
  • Garage Description: Attached Garage


  • County: Fairfield
  • Neighborhood: Tokeneke
  • Driving Directions: Searles to Contentment. Second to last house on the right.

School Information

  • Elementary School: Tokeneke
  • Middle School: Middlesex
  • High School: Darien


  • Community Name: Tokeneke
  • Association: Yes

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Oil, Propane
  • Heating Fuel: Oil, Propane


  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Tudor
  • Exterior Const.: Concrete, Stucco, Wood
  • Basement Desc.: Interior Access, Partial, Unfinished
  • Roof: Slate
  • Attic: Yes
  • Square Feet: 6,449
  • Year Built: 1900

Lot Features

  • Lot Size (Acres): 3.21
  • Zoning: R-1
  • Lot Description: Water View, Level Lot, Treed, Fence - Partial

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Direct Waterfront, Frontage, L. I. Sound Frontage, Beach

Financial Considerations

  • Association Fee: $3,677
  • Assessment Amount: $4,839,240
  • Tax Amount: $78,202
  • Tax Year: July 2017-June 2018

Disclosures and Reports

  • Exclusions: all chandeliers and sconces
  • Property ID: 109220

Listed by Halstead Property, Eileen Hanford

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Schools serving 42 Contentment Island Road

School District:
Darien Public Schools
School Name
Tokeneke Elementary School
7 Old Farm Rd, Darien, CT 06820
1.3 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
2.4 mi
Darien High School
80 High School Ln, Darien, CT 06820
2.7 mi
Disclaimer: School data provided by Pitney Bowes. School attendance boundaries are for reference only. Contact the school directly to verify enrollment eligibility.

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Community Info

Community Infofor 42 Contentment Island Road

42 Contentment Island Road, Darien, CT 06820 (MLS# 99157920) is a Single Family property with 6 bedrooms, 4 full bathrooms and 2 partial bathrooms. 42 Contentment Island Road is currently listed for $9,850,000 and was received on August 24, 2016. Want to learn more about 42 Contentment Island Road? Do you have questions about finding other Single Family real estate for sale in Tokeneke? You can browse all Tokeneke real estate or contact a Coldwell Banker agent to request more information.

Listed by Halstead Property, Eileen Hanford

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