17 Contentment Island Road

Darien, CT 06820

$9,895,000 PRICE
6 Beds
4/1 Baths
7,174 Sqft
2.45 Acres
$4,539 HOA

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.

Additional Information

ADDITIONAL INFORMATION

ASSOCIATION FEE / FREQUENCY: $4,539.00 / Annually
ATTIC DESCRIPTION: Unfinished, Floored, Pull-Down Stairs
AVERAGE DAYS ON MARKET: 113
BASEMENT DESCRIPTION: Partial, Unfinished, Interior Access, Partial With Hatchway, Concrete Floor
DAYS ON MARKET: 113
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

Mortgage Calculator

Mortgage Term

Years

Interest Rate

%/Year

Principal Amount

in US Dollars

Down Payment

Amortization

Years

Your Estimated Payment

-- Monthly Payment

Down Payment
Required --
Mortgage
Principal --
Still Owing at the
End of Term --

Location for 17 Contentment Island Road, Darien, CT

Request More Info

Schedule a Showing Best Day/Time

Yes, I would like more information from Sotheby's International Realty. Please use and/or share my information with a Sotheby's International Realty agent to contact me about my real estate needs.

By clicking Send Message, I agree a Sotheby's International Realty Agent may contact me by phone or text message including by automated means about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Policy

Community

Darien

Fairfield County, Connecticut

Darien, a residential community along Long Island Sound, features many restored Colonial homes, adding to its charm and historic value. The heart of the community is found in its civic activities, top-rated...

Market Stats for Darien, Connecticut

An exclusive report that informs you of residential real estate sales activity and trends in Darien, Connecticut.

Request More Info for 17 Contentment Island Road, Darien, CT

Darien Brokerage
1057 Post Road
Darien, CT 06820
O

Schedule a Showing Best Day/Time

Yes, I would like more information from Sotheby's International Realty. Please use and/or share my information with a Sotheby's International Realty agent to contact me about my real estate needs.