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.
For sale
$9,895,000
17 Contentment Island Road, Darien, CT 06820
6beds
7,174sqft
Est.:
Single Family Residence
Built in 1909
2.45 Acres Lot
$-- Zestimate®
$1,379/sqft
$378/mo HOA
What's special
Waterfront estateSoaring ceilingsSophisticated sunroomGrand primary suiteOversized waterfront balconyExquisitely landscaped groundsExpansive kitchen
- 7 hours |
- 643 |
- 16 |
Zillow last checked: 8 hours ago
Listing updated: 15 hours ago
Listed by:
Douglas Milne (203)667-0344,
Houlihan Lawrence 203-655-8238
Source: Smart MLS,MLS#: 24115997
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Balcony/Deck, Fireplace, Full Bath, Sliders, Hardwood Floor
- Level: Upper
- Area: 540 Square Feet
- Dimensions: 15 x 36
Bedroom
- Level: Upper
- Area: 312 Square Feet
- Dimensions: 13 x 24
Bedroom
- Level: Upper
- Area: 225 Square Feet
- Dimensions: 15 x 15
Bedroom
- Level: Upper
- Area: 204 Square Feet
- Dimensions: 12 x 17
Bedroom
- Level: Upper
- Area: 204 Square Feet
- Dimensions: 12 x 17
Bedroom
- Level: Upper
- Area: 336 Square Feet
- Dimensions: 14 x 24
Dining room
- Features: 2 Story Window(s), Fireplace
- Level: Main
- Area: 306 Square Feet
- Dimensions: 17 x 18
Family room
- Features: Fireplace
- Level: Main
- Area: 360 Square Feet
- Dimensions: 15 x 24
Kitchen
- Features: High Ceilings, Dining Area
- Level: Main
- Area: 432 Square Feet
- Dimensions: 18 x 24
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 493 Square Feet
- Dimensions: 17 x 29
Rec play room
- Features: Cathedral Ceiling(s), Fireplace
- Level: Upper
- Area: 483 Square Feet
- Dimensions: 21 x 23
Sun room
- Features: Bookcases, Tile Floor
- Level: Main
- Area: 500 Square Feet
- Dimensions: 20 x 25
Heating
- Hot Water, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Gas Cooktop, Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Upper Level
Features
- In-Law Floorplan
- Doors: French Doors
- Basement: Partial,Unfinished,Interior Entry,Concrete
- Attic: Floored,Pull Down Stairs
- Number of fireplaces: 4
Interior area
- Total structure area: 7,174
- Total interior livable area: 7,174 sqft
- Finished area above ground: 7,174
Video & virtual tour
Property
Parking
- Total spaces: 6
- Parking features: Detached, Driveway, Garage Door Opener, Paved
- Garage spaces: 3
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio
- Exterior features: Balcony, Garden, Underground Sprinkler
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Walk to Water, Beach Access, Association Required, Access
Lot
- Size: 2.45 Acres
- Features: Few Trees
Details
- Additional structures: Guest House
- Parcel number: 109167
- Zoning: R-1
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Stone
- Foundation: Block, Concrete Perimeter
- Roof: Slate
Condition
- New construction: No
- Year built: 1909
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & HOA
Community
- Security: Security System
- Subdivision: Contentment Island
HOA
- Has HOA: Yes
- Services included: Security
- HOA fee: $4,539 annually
Location
- Region: Darien
Financial & listing details
- Price per square foot: $1,379/sqft
- Tax assessed value: $7,041,510
- Annual tax amount: $109,003
- Date on market: 1/15/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 12/10/2025 | Listing removed | $9,895,000$1,379/sqft |
Source:  Smart MLS #24115997 Report a problem | ||
| 10/29/2025 | Price change | $9,895,000-9.2%$1,379/sqft |
Source: Smart MLS #24115997 Report a problem | ||
| 9/2/2025 | Listed for sale | $10,895,000$1,519/sqft |
Source: Smart MLS #24115997 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $109,003 +5.4% | $7,041,510 |
| 2024 | $103,440 -3.6% | $7,041,510 +15.6% |
| 2023 | $107,281 +2.2% | $6,092,030 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$66,893/mo
Principal & interest
$49117
Property taxes
$13935
Other costs
$3841
Climate risks
Neighborhood: Tokeneke
Nearby schools
GreatSchools rating
- 8/10Tokeneke Elementary SchoolGrades: PK-5Distance: 1.1 mi
- 9/10Middlesex Middle SchoolGrades: 6-8Distance: 2.5 mi
- 10/10Darien High SchoolGrades: 9-12Distance: 2.6 mi
Schools provided by the listing agent
- Elementary: Tokeneke
- Middle: Middlesex
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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