17 Contentment Island Road

Closed 3/30/26Virtual Tour
Closed 3/30/26Virtual Tour
Gallery Image 1
Sold
Last Sold Price
$9,420,000
6 beds7,174 sqft$1,313/sqft
17 Contentment Island Rd, Darien, CT 06820
Single FamilyProperty Type
2.45 acresLot Size
1909Year Built
$1,313/sq ftPrice per sq ft
$4,539/yrHOA Fees
6 carsParking Spaces

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.
  • Listed by: Douglas Milne 203.667.0344 douglasdmilne@gmail.com • Houlihan Lawrence
Listing closed: 03/30/2026 12:00 AM • Source: SMARTMLS, MLS#: 24115997
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Location

Listing Courtesy of Houlihan Lawrence, Douglas Milne

Sold By Compass Connecticut, LLC, Casey Lange

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$57,343 per month

30 year fixed, 6.55% Interest

Principal and Interest

$47,881

Property Taxes

$9,084

HOA Dues

$378

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Property Information for 17 Contentment Island Road

Property Details
  • MLS Type: Residential
  • County: Fairfield County
  • 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
Building Information
  • Year Built: 1909
  • Lot Size: 2.45 AC / 106,722 SF
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
Virtual Tour
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 Record2025$109,003 ($9,084 / month)
Home Facts
Beds6Baths4.5Total Finished SqFt7,174 SqFtAbove Grade Finished SqFt7,174 SqFtUnfinished Basement SqFt330 SqFtStories3Lot Size106,722 SqFtStyleSingle Family ResidenceYear Built1909Year Renovated1909ZoningR-1CountyWESTERN CONNECTICUTAPNDARI M:67 B:56

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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 17 Contentment Island Road, Darien, CT 06820
$9,420,000
6
7,174
106,722
1 Tokeneke Beach Drive, Darien, CT 06820
$2,575,000
4
4.5
4,556
43,996
15 Contentment Island Road, Darien, CT 06820
–
2
1
1,401
51,401
11 Contentment Island Road, Darien, CT 06820
$2,591,000
4
4,521
–
23 Contentment Island Road, Darien, CT 06820
$3,500,000
4
7
5,577
138,085
26 Contentment Island Road, Darien, CT 06820
$1
3
3
3,514
63,075

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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.