25 Tokeneke Trail - Where the Sky meets the Sea. Wake up to breathtaking sunrises, spend afternoons on the water, and end each day with sunset views from your private terrace. 25 Tokeneke Trail isn't just a home-it's a lifestyle. Perfectly perched above the shoreline and not in a flood zone, this stunning waterfront retreat offers direct access to the water with its own private beach and dock. Designed for seamless indoor-outdoor living, nearly every room frames panoramic water views. Multiple stone terraces, a firepit, and lush landscaping create the perfect setting for entertaining or quiet relaxation. Inside, over 6,000 sq. ft. of refined living space includes five bedrooms, seven baths, and a private studio suite over the detached garage ideal for a guest house or private retreat. Minutes from downtown Darien and the train to NYC, this rare property blends the serenity of coastal living with the best of modern luxury.
Sold for $8,695,000
$8,695,000
25 Tokeneke Trail, Darien, CT 06820
5beds
6,108sqft
Single Family Residence
Built in 1910
0.6 Acres Lot
$9,127,900 Zestimate®
$1,424/sqft
$7,061 Estimated rent
Home value
$9,127,900
$8.22M - $10.13M
$7,061/mo
Zestimate® history
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List your homeWhat's special
Waterfront retreatWater viewsPrivate beachPanoramic water viewsBreathtaking sunrisesStone terracesPrivate terrace
Zillow last checked:
Listing updated:
Listed by:
Team AFA at William Raveis Real Estate,
Nellie Snell (203)979-9149,
William Raveis Real Estate 203-655-1423
Bought with:
Nellie Snell, RES.0800556
William Raveis Real Estate
Source: Smart MLS,MLS#: 24126696
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 8
- Full bathrooms: 5
- 1/2 bathrooms: 3
Primary bedroom
- Features: High Ceilings, Balcony/Deck, Bedroom Suite, Built-in Features, Dressing Room, Walk-In Closet(s)
- Level: Upper
- Area: 256.8 Square Feet
- Dimensions: 16.02 x 16.03
Bedroom
- Features: High Ceilings, Built-in Features, Hardwood Floor
- Level: Upper
- Area: 171.42 Square Feet
- Dimensions: 10.06 x 17.04
Bedroom
- Features: High Ceilings, Hardwood Floor
- Level: Upper
- Area: 227.26 Square Feet
- Dimensions: 15.1 x 15.05
Bedroom
- Features: High Ceilings, Hardwood Floor
- Level: Upper
- Area: 407.1 Square Feet
- Dimensions: 27.05 x 15.05
Bedroom
- Features: Beamed Ceilings, Bedroom Suite, Cedar Closet(s)
- Level: Third,Upper
- Area: 240.46 Square Feet
- Dimensions: 17.09 x 14.07
Primary bathroom
- Features: Double-Sink, Full Bath, Stall Shower
- Level: Upper
- Area: 121.38 Square Feet
- Dimensions: 10.09 x 12.03
Bathroom
- Features: High Ceilings, Tub w/Shower
- Level: Upper
- Area: 48.82 Square Feet
- Dimensions: 8.07 x 6.05
Bathroom
- Features: Tub w/Shower
- Level: Third,Upper
- Area: 78.24 Square Feet
- Dimensions: 7.1 x 11.02
Dining room
- Features: Bay/Bow Window, High Ceilings, Hardwood Floor
- Level: Main
- Area: 17.77 Square Feet
- Dimensions: 1.04 x 17.09
Kitchen
- Features: High Ceilings, Breakfast Nook, Built-in Features, Dining Area, Pantry, Hardwood Floor
- Level: Main
- Area: 198.39 Square Feet
- Dimensions: 14.1 x 14.07
Living room
- Features: High Ceilings, Built-in Features, Fireplace, Patio/Terrace, Sliders, Hardwood Floor
- Level: Main
- Area: 393.11 Square Feet
- Dimensions: 23.07 x 17.04
Living room
- Features: High Ceilings, Wet Bar, Entertainment Center, Fireplace, Hardwood Floor
- Level: Main
- Area: 337.94 Square Feet
- Dimensions: 14.04 x 24.07
Office
- Features: High Ceilings, Built-in Features, Full Bath
- Level: Main
- Area: 195.84 Square Feet
- Dimensions: 13.03 x 15.03
Heating
- Forced Air, Hot Water, Propane
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven/Range, Microwave, Range Hood, Ice Maker, Dishwasher, Instant Hot Water, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Main Level
Features
- Sound System, Entrance Foyer, Smart Thermostat
- Doors: French Doors
- Basement: Full,Heated,Cooled
- Attic: Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 6,108
- Total interior livable area: 6,108 sqft
- Finished area above ground: 5,583
- Finished area below ground: 525
Property
Parking
- Total spaces: 4
- Parking features: Attached, Detached, Driveway, Garage Door Opener, Private
- Attached garage spaces: 4
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 32" Minimum Door Widths, Accessible Hallway(s)
Features
- Patio & porch: Terrace, Patio
- Exterior features: Rain Gutters, Lighting, Awning(s), Underground Sprinkler
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Dock or Mooring, Beach Access, Association Required
Lot
- Size: 0.60 Acres
- Features: Level, Landscaped
Details
- Additional structures: Guest House
- Parcel number: 109260
- Zoning: R-1
- Other equipment: Entertainment System
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Concrete Perimeter, Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1910
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities, Cable Available
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Library, Park, Playground, Private School(s), Public Rec Facilities, Near Public Transport
Location
- Region: Darien
- Subdivision: Tokeneke
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $2,500 annually
- Services included: Security, Snow Removal, Road Maintenance
Price history
| Date | Event | Price |
|---|---|---|
| 11/21/2025 | Sold | $8,695,000$1,424/sqft |
Source:  Smart MLS #24126696 Report a problem | ||
| 10/15/2025 | Pending sale | $8,695,000$1,424/sqft |
Source: Smart MLS #24126696 Report a problem | ||
| 9/16/2025 | Listed for sale | $8,695,000-1.1%$1,424/sqft |
Source: Smart MLS #24126696 Report a problem | ||
| 9/16/2025 | Listing removed | $8,795,000$1,440/sqft |
Source:  Greenwich MLS, Inc. #122897 Report a problem | ||
| 5/29/2025 | Listed for sale | $8,795,000+122.7%$1,440/sqft |
Source: Smart MLS #24092867 Report a problem | ||
| 12/22/2021 | Sold | $3,950,000-10.1%$647/sqft |
Source: Smart MLS #170205437 Report a problem | ||
| 11/15/2021 | Contingent | $4,395,000$720/sqft |
Source: Smart MLS #170205437 Report a problem | ||
| 8/16/2021 | Price change | $4,395,000-6.4%$720/sqft |
Source: Smart MLS #170205437 Report a problem | ||
| 7/7/2021 | Listed for sale | $4,695,000-4.2%$769/sqft |
Source: Smart MLS #170205437 Report a problem | ||
| 7/9/2020 | Listing removed | $4,899,000$802/sqft |
Source: Houlihan Lawrence #35185 Report a problem | ||
| 5/13/2020 | Listing removed | $17,000$3/sqft |
Source: Houlihan Lawrence #35956 Report a problem | ||
| 5/7/2020 | Listed for rent | $17,000$3/sqft |
Source: Houlihan Lawrence #35956 Report a problem | ||
| 5/4/2020 | Price change | $4,899,000-1%$802/sqft |
Source: Houlihan Lawrence #35185 Report a problem | ||
| 11/26/2019 | Price change | $4,950,000-9.9%$810/sqft |
Source: Houlihan Lawrence #35185 Report a problem | ||
| 9/18/2019 | Price change | $5,495,000-3.5%$900/sqft |
Source: Houlihan Lawrence #35185 Report a problem | ||
| 6/12/2019 | Listed for sale | $5,695,000+321.9%$932/sqft |
Source: Houlihan Lawrence #35185 Report a problem | ||
| 5/12/1993 | Sold | $1,350,000$221/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $63,445 +33.2% | $4,098,500 +26.4% |
| 2024 | $47,648 -4.1% | $3,243,590 +15% |
| 2023 | $49,662 +2.2% | $2,820,090 |
| 2022 | $48,590 +2.3% | $2,820,090 |
| 2021 | $47,490 +3.1% | $2,820,090 |
| 2020 | $46,052 -0.9% | $2,820,090 |
| 2019 | $46,447 0% | $2,820,090 -2.4% |
| 2018 | $46,468 -0.5% | $2,889,810 |
| 2017 | $46,699 +2.5% | $2,889,810 |
| 2016 | $45,572 +2.7% | $2,889,810 |
| 2015 | $44,359 +2.3% | $2,889,810 |
| 2014 | $43,376 -6.4% | $2,889,810 -17.9% |
| 2013 | $46,339 +3.9% | $3,518,550 |
| 2012 | $44,615 +3.9% | $3,518,550 |
| 2011 | $42,926 +3.9% | $3,518,550 |
| 2010 | $41,308 +3.3% | $3,518,550 |
| 2009 | $40,006 -3% | $3,518,550 +24.1% |
| 2008 | $41,252 +4.9% | $2,835,210 |
| 2007 | $39,324 -25.4% | $2,835,210 -30% |
| 2005 | $52,735 +55.6% | $4,050,300 +42.9% |
| 2004 | $33,881 +53.7% | $2,835,210 +68% |
| 2003 | $22,041 -6.9% | $1,687,700 |
| 2001 | $23,662 +7.4% | $1,687,700 -30% |
| 2000 | $22,041 +82.9% | $2,411,000 +254.6% |
| 1999 | $12,049 | $679,970 |
Find assessor info on the county website
Neighborhood: Tokeneke
Nearby schools
GreatSchools rating
- 9/10Tokeneke Elementary SchoolGrades: PK-5Distance: 1 mi
- 10/10Middlesex Middle SchoolGrades: 6-8Distance: 2.1 mi
- 10/10Darien High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Tokeneke
- Middle: Middlesex
- High: Darien
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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- Connecticut
- Fairfield County
- Darien
- 06820
- Tokeneke
- 25 Tokeneke Trail
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