17 Contentment Island Rd

Darien, CT 06820

$9,895,000
Price
6
Beds
7,174 Sq. Ft.
$1,379 / Sq. Ft.
7,174
Sq. Ft.
$1,379
per Sq. Ft.
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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....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.
  1. Listed by Douglas Milne • Houlihan Lawrence
    P: (203)-667-0344 C: (203)-667-0344 douglasdmilne@gmail.com

Property Details for 17 Contentment Island Road

Basement Description
Partial, Unfinished, Interior Access, Partial With Hatchway, Concrete Floor
Direct Waterfront
Yes
Garages Number
3
Neighborhood
Contentment Island
Style
Colonial
Garage Parking Info
Detached Garage, Driveway
Swimming Pool
No
LISTING UPDATED: 01/15/2026 11:46 PM

Property Details for 17 Contentment Island Road

StatusActive
MLS #24115997
Days on Market105
Taxes-
HOA Fees$4,539 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1909
Lot Size2.45 AC / 106,722 SF
CountyFairfield County

Location

Listing Courtesy of Houlihan Lawrence, Douglas Milne
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Building Information for 17 Contentment Island Road

Stories-Year Built1909Building Size-Lot Size2.45 AC / 106,722 SF

Payment Calculator

$57,689 per month

30 year fixed, 6.15% Interest

Principal and Interest

$48,227

Property Taxes

$9,084

HOA Dues

$378

The Payment Calculator is for illustrative purposes only.

Property Information for 17 Contentment Island Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Searles Rd to Contentment Island Road
  • Elementary School: Tokeneke
  • High School: Per Board of Ed
  • Latitude: 41.058152
  • Longitude: -73.45404
  • Middle Jr High School: Middlesex
  • State: Connecticut
Parking
  • Parking Total Spaces: 6
HOA and Fees
  • Association Fee Includes: Security Service
  • HOA Fee Amount: 4539
  • HOA Fee Frequency: Annually
  • Home Owner's Assocation: Yes
  • Special Association Assessment: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $109,003
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Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Garden Area, Guest House, French Doors, Underground Sprinkler, Patio
  • Waterfront Description: L. I. Sound Frontage, Walk to Water, Beach Rights, Association Required, Access
Interior Features
  • Appliances Included: Gas Cooktop, Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Attic Description: Unfinished, Floored, Pull-Down Stairs
  • Cooling System: Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 4
  • Interior Features: Auto Garage Door Opener, Security System
  • Laundry Room Info: Upper Level
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 29.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 17.0
Room 2
  • Room Entry Order: 10
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 3
  • Room Entry Order: 11
  • Room Length: 24.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 4
  • Room Entry Order: 12
  • Room Features: Cathedral Ceiling,Fireplace
  • Room Length: 23.0
  • Room Level: Upper
  • Room Type: Rec/Play Room
  • Room Width: 21.0
Room 5
  • Listing Key: 3B3DF84B0E3BCC44E063E201100AD3AD
  • Room Entry Order: 2
  • Room Features: 2 Story Window(s),Fireplace
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 17.0
Room 6
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Dining Area
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 18.0
Room 7
  • Room Entry Order: 4
  • Room Features: Fireplace
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 15.0
Room 8
  • Room Entry Order: 5
  • Room Features: Book Shelves,Tile Floor
  • Room Length: 25.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 20.0
Room 9
  • Listing Key: 3B3DF84B0E3BCC44E063E201100AD3AD
  • Room Entry Order: 6
  • Room Features: Balcony/Deck,Fireplace,Full Bath,Sliders,Hardwood Floor
  • Room Length: 36.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 15.0
Room 10
  • Room Entry Order: 7
  • Room Length: 24.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 11
  • Room Entry Order: 8
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 12
  • Room Entry Order: 9
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Property
Property and Assessments
  • Color: Beige
  • Construction Description: Frame, Stone, Concrete
  • Driveway Type: Paved
  • Exterior Siding: Stone
  • Foundation Type: Block, Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Slate
  • Year Built: 1909
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached
  • In Law Apartment: Yes
  • Living Area SQFT Per Public Records: 7174
Lot Information
  • Lot Description: Lightly Wooded, Water View
  • Parcel Number: 109167
  • Sq Ft Est Heated Above Grade: 7174.0
  • Sq Ft Total: 7174.0
  • Zoning: R-1
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, 50 Gallon Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Vacant

Public Records for 17 Contentment Island Road

Taxable ValueLand$4,722,830Additions$2,318,680Total$7,041,510
Tax Record2024$109,003 ($9,084 / month)
Home Facts
Beds6Baths4.5Total Finished SqFt7,174 SqFtAbove Grade Finished SqFt7,174 SqFtStories3Lot Size106,722 SqFtStyleSingle Family ResidenceYear Built1909ZoningR-1CountyFAIRFIELDAPNDARI M:67 B:56Fireplace TypeHas Fireplace

Schools near 17 Contentment Island Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Tokeneke Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Tokeneke Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 17 Contentment Island Road, Darien, CT 06820

17 Contentment Island Road is a single family home for sale in Darien, CT 06820. This property was listed for sale on September 2, 2025 by Houlihan Lawrence, it's currently listed at $9,895,000. This listing's school district is Darien School District. Nearby schools include Tokeneke Elementary School, Middlesex Middle School and Darien High School. 17 Contentment Island Road is a 6-bed, 5-bath, 7,174 sqft single family home built in 1909.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Houlihan Lawrence, Douglas Milne

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.