17 Contentment Island Rd, Darien, CT 06820
- $9,420,000
- 6
- BD
- 5
- BA
- 7,174
- SqFt
- Sold Price
- $9,420,000
- List Price
- $9,895,000
- Status
- CLOSED
- MLS#
- 24115997
- Closing Date
- Mar 30, 2026
- Year Built
- 1909
- Style
- Colonial
- Bedrooms
- 6
- Bathrooms
- 5
- Acres
- 2.45
- Living Area
- 7,174
Property 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. 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.
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Additional Information
- Taxes
- $109,003
- Hoa Fee
- $4,539
- Lot Size
- 106,722
- Interior Features
- Security System
- Heating
- Hot Water
- Cooling System Type
- Window/Wall
- Sewer
- Septic Tank
- Water Source
- Public
- Appliances
- Gas Cooktop, Gas Range, Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
- Fireplaces
- 4
- Basement
- Partial, Unfinished, Interior Entry, Concrete
- Exterior Features
- Balcony, Garden, Guest Quarters, Sprinkler System, Patio
- Garage Spaces
- 3
- Parking Spaces
- 6
- Elementary School
- Tokeneke
- Middle School
- Middlesex
- High School
- Per Board of Ed
Mortgage Calculator
Listing courtesy of Douglas Milne from Houlihan Lawrence. (203) 667-0344 (203) 655-8238
Selling Office: Compass Connecticut, LLC.The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.