Home / Recently Sold / Darien
Closed · For Sale
$9,895,000
17 Contentment Island Road, Darien, Connecticut 06820
6 beds 5 baths 7,174 sq ft Single Family For Sale Built 1909
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About this home

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.

Status
Closed
Type
Single Family For Sale
Price
$9,895,000
Beds
6
Baths
5
Interior
7,174 sq ft
Lot
2.45 ac
Year Built
1909
MLS #
24115997
ZIP
06820
Days on Market
113
Heat
Oil · Hot Water
Cooling
Window Unit
Water
Public Water Connected
Sewer
Septic
Parking
Detached Garage, Driveway (3-car)
Laundry
Upper Level

Flood risk: check the FEMA flood map for this address.

HOA & Fees

HOA fee
$4,539 / Annually
Fee includes
Security Service

Schools

Elementary
Tokeneke
Middle / Jr High
Middlesex
High School
Per Board of Ed

Taxes

Property tax
$109,003 (July 2025-June 2026)
Assessed value
$7,041,510

Interior

Appliances
Gas Cooktop, Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer
Basement
Partial, Unfinished, Interior Access, Partial With Hatchway, Concrete Floor
Attic
Unfinished, Floored, Pull-Down Stairs
Fireplaces
4
Total rooms
12

Building & Exterior

Style
Colonial
Roof
Slate
Siding
Stone
Exterior features
Balcony, Garden Area, Guest House, French Doors, Underground Sprinkler, Patio
Foundation
Block, Concrete
New construction
No/Resale

Lot & Land

Zoning
R-1
Lot
Lightly Wooded, Water View
Waterfront
L. I. Sound Frontage, Walk to Water, Beach Rights, Association Required, Access
Direct waterfront
Yes

Listing & sale history

Every time this exact home has come to market in the MLS data this site tracks. Where a sale closed, the recorded sale price is shown; "asking" marks a price the home was listed at rather than what it sold for.

2026-03-30Sold — $9,420,000 asked $9,895,000 (this listing)MLS 24115997

Public record

From the Darien assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Year built1909
Living area7,174 sq ft
Total rooms10
Lot size2.45 acres
Stories3
HeatCOLONIAL
ExteriorMAS&FR
Assessed value$7,041,510
Town appraisal$10,059,300
Last recorded sale2017
Listing courtesy of Houlihan Lawrence — Douglas Milne · (203) 655-8238

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