Date
Details
Price
Change
Source
10/26/2026
Listed
$60,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/19
$60,000 Just Listed
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1/19
Property Description & Video
25 Contentment Island Road, Darien, CTVideo Tour of 25 Contentment Island Road, Darien, CT.
Introducing one of Tokeneke's most iconic waterfront estates available for the first time in 40 years. A rare opportunity to rent a brand-new coastal masterpiece. "Never again" panoramic views of the Long Island Sound that will take your breath away due to the unique location of the Main House. Unparalleled serenity, beauty and access to the water, in the heart of Darien's most coveted enclave. Set on approximately 2.88 acres of exquisitely landscaped grounds with 180 feet of your own private beach! Moor your boat, enjoy the beach, kayak, take a dip in the heated waterfront pool.
Full Property Details
Full Property Details for 25 Contentment Island Rd
General
- Rent: $60,000
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24211025
- Updated: 10/27/2026
- Added to Site: 6 day(s) ago
Rental Information
- Rental Type: Yearly Unfurnished
- Lease Terms: Per Month
Interior
- Number of Rooms: 11
- Interior Features: Open Floor Plan, Security System
- Fireplace: Yes
- Number of Fireplaces: 3
- Appliances: Gas Cooktop, Oven/Range, Microwave, Subzero, Dishwasher
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 5
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
- Primary Bedroom: Primary Bedroom - Balcony/Deck, Upper
- Bedroom 1: Bedroom - Balcony/Deck, Upper
- Bedroom 2: Bedroom, Upper
- Bedroom 3: Bedroom - Balcony/Deck, Upper
- Bedroom 4: Bedroom, Upper
Other Rooms
- Living Room: Living Room - Balcony/Deck, Fireplace, Main
- Dining Room: Dining Room, Main
- Laundry: Upper Level
- In-Law/Au Pair Suite: Yes
Additional Information
- Pool: Yes
- Pool Description: Heated, In Ground Pool
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 4
- Parking: Detached Garage, Driveway
Location
- County: Fairfield
- Neighborhood: Tokeneke
- Driving Directions: Exit 12 off Route 95.
School Information
- Elementary School: Per Board of Ed
- High School: Per Board of Ed
Community
- Community Name: Tokeneke
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Electric, Propane
- Heating Fuel: Electric, Propane
- Water Heater: Electric, 80 Gallon Tank
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Colonial
- Construction Status: Torn Down & Rebuilt
- Basement Desc.: None
- Attic: Yes
- Square Feet: 6,750
- Above Ground: 6,750 Sq. Ft.
- Year Built: 2026
Lot Features
- Lot Size (Acres): 2.88
- Driveway/Sidewalk: Crushed Stone
- Zoning: R-1
- Lot Description: Professionally Landscaped, Water View
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: L. I. Sound Frontage, Beach, Dock or Mooring, View, Access
Financial Considerations
- Tenant Pays: Air Conditioning, All Utilities, Cable TV, Electricity, Exterior Maintenance, Grounds Maintenance, Heat, Hot Water, Insurance, Internet, Security System, Snow Removal
Disclosures and Reports
- Property ID: 109207
Listed by Douglas Elliman of Connecticut, Christa Kenin
Schools
Schools serving 25 Contentment Island Rd
School District:Darien School District
| Name | Grades | Distance |
|---|---|---|
Tokeneke Elementary School 7 Old Farm Road, Darien, CT 06820 | K-5 | 1.3 mi |
Middlesex Middle School 204 Hollow Tree Ridge Road, Darien, CT 06820 | 6-8 | 2.5 mi |
Darien High School 80 High School Lane, Darien, CT 06820 | 9-12 | 2.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 25 Contentment Island Rd
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- Townhouse
- Active
- Updated 5 days ago
- 2Beds
- 3Total Baths
- 1,481Sq. Ft.
Listed by Michael Pavlicin (203) 858-1827
- Apartment
- Active
- Updated 10 days ago
- 1Bed
- 1Total Bath
- 770Sq. Ft.
Listed by Shahla Husain (646) 303-0743
- Apartment
- Active
- Updated 4 days ago
- 1Bed
- 1Total Bath
- 750Sq. Ft.
Listed by Demetri Dassouras (203) 286-9435
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- Condo
- Active
- Updated 10 days ago
- 1Bed
- 1Total Bath
- 873Sq. Ft.
Listed by Aurelia Gilbert (203) 451-3178
- Townhouse
- Active
- Updated 2 days ago
- 2Beds
- 2Total Baths
- 1,272Sq. Ft.
Listed by Melanie Healey (203) 249-9149
- Condo
- Active
- Updated 2 days ago
- 1Total Bath
- 680Sq. Ft.
Listed by The Richard Breglia Team (203) 273-3916
- Townhouse
- Active
- Updated 16 hours ago
- 1Bed
- 2Total Baths
- 725Sq. Ft.
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- Single Family
- Closed
- 5Beds
- 6Total Baths
- 7,157Sq. Ft.
Listed and Sold by Inna Agujen
- Single Family
- Closed
- 4Beds
- 7Total Baths
- 6,821Sq. Ft.
Listed by Cindy Saul
Sold by Corcoran Centric Realty
Sold by Corcoran Centric Realty
25 Contentment Island Road, Darien, CT 06820 (MLS# 24211025) is a Single Family property with 5 bedrooms, 5 full bathrooms and 1 partial bathroom. 25 Contentment Island Road is currently listed for rent at $60,000 and was received on October 26, 2026. Want to learn more about 25 Contentment Island Road? Do you have questions about finding other real estate for sale or rent in Tokeneke? You can browse all Tokeneke rentals or contact a Coldwell Banker agent to request more information.