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$9,895,000

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 7,174 Sq. Ft.
  • 3 Car Garage
  • Updated 1 day ago
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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.

Full Property Details for 17 Contentment Island Rd

General

  • Price: $9,895,000
  • HOA FEE: $378/month
  • HOA FEE FREQ.: Annually
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24115997
  • Updated: 1/15/2026
  • Added to Site: 136 day(s) ago

Interior

  • Number of Rooms: 12
  • Interior Features: Auto Garage Door Opener, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Gas Cooktop, Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 6
  • Primary Bedroom: Primary Bedroom - Balcony/Deck, Fireplace, Full Bath, Sliders, Hardwood Floor, 36 x 15, Upper
  • Bedroom 1: Bedroom, 15 x 15, Upper
  • Bedroom 2: Bedroom, 17 x 12, Upper
  • Bedroom 3: Bedroom, 17 x 12, Upper
  • Bedroom 4: Bedroom, 24 x 13, Upper
  • Bedroom 5: Bedroom, 24 x 14, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 29 x 17, Main
  • Family Room: Family Room - Fireplace, 24 x 15, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Dining Area, 24 x 18, Main
  • Dining Room: Dining Room - 2 Story Window(s), Fireplace, 18 x 17, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Cathedral Ceiling, Fireplace, 23 x 21, Upper
  • Rec Room: Cathedral Ceiling, Fireplace, 23 x 21, Upper
  • Laundry: Upper Level
  • In-Law/Au Pair Suite: Yes

Exterior

  • Exterior Features: Balcony, Garden Area, Guest House, French Doors, Underground Sprinkler, Patio
  • Color: Beige

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 6
  • Parking: Detached Garage, Driveway

Location

  • County: Fairfield
  • Neighborhood: Contentment Island
  • Driving Directions: Searles Rd to Contentment Island Road

School Information

  • Elementary School: Tokeneke
  • Middle School: Middlesex
  • High School: Per Board of Ed

Community

  • Community Name: Contentment Island
  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Security Service

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, 50 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Stone
  • Basement Desc.: Partial, Unfinished, Interior Access, Partial With Hatchway, Concrete Floor
  • Roof: Slate
  • Attic: Yes
  • Square Feet: 7,174
  • Above Ground: 7,174 Sq. Ft.
  • Year Built: 1909

Lot Features

  • Lot Size (Acres): 2.45
  • Driveway/Sidewalk: Paved
  • Zoning: R-1
  • Lot Description: Lightly Wooded, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: L. I. Sound Frontage, Walk to Water, Beach Rights, Association Required, Access

Financial Considerations

  • Association Fee: $4,539
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $7,041,510
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 109167

Listed by Houlihan Lawrence, Douglas Milne

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Listing agent

— 17 Contentment Island Rd —

  • Douglas Milne

    Houlihan Lawrence

Agent Contact: (203) 667-0344 Office Contact: (203) 655-8238

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 17 Contentment Island Rd

School District:Darien School District
NameGradesDistance
Tokeneke Elementary School
7 Old Farm Road, Darien, CT 06820
K-51.1 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-82.5 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-122.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 17 Contentment Island Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/29/2025
Price Reduced
$9,895,000
-9.18%
MLS
7/17/2025
Listed
$10,895,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 17 Contentment Island Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$109,003
5%
$7,041,510
—
2023
$103,440
-4%
$7,041,510
16%
2023
$107,281
2%
$6,092,030
—
2022
$104,966
2%
$6,092,030
—
2021
$102,590
3%
$6,092,030
—
2020
$99,483
-1%
$6,092,030
—
2019
$100,336
-7%
$6,092,030
-9%
2018
$107,446
—
$6,681,990
—
2017
$107,981
2%
$6,681,990
—
2016
$105,375
3%
$6,681,990
—
2015
$102,569
2%
$6,681,990
—
2014
$100,297
20%
$6,681,990
6%
2012
$83,382
—
$6,331,220
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Houlihan Lawrence, Douglas Milne

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17 Contentment Island Road, Darien, CT 06820 (MLS# 24115997) is a Single Family property with 6 bedrooms, 4 full bathrooms and 1 partial bathroom. 17 Contentment Island Road is currently listed for $9,895,000 and was received on September 02, 2025. Want to learn more about 17 Contentment Island Road? Do you have questions about finding other Single Family real estate for sale in Darien? You can browse all Darien real estate or contact a Coldwell Banker agent to request more information.

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