Set on a quiet cul-de-sac within Darien's prestigious Tokeneke Private Association, this beautifully updated 4-bedroom, 3.5-bath Colonial offers refined living in one of the town's most coveted coastal neighborhoods. Thoughtfully renovated with sophisticated transitional design, the home blends timeless elegance with a fresh, modern aesthetic. Situated on 1.4 private acres, the property offers exceptional natural light, expansive living spaces, and effortless flow. The dramatic family room features vaulted ceilings and generous scale, ideal for everyday living and entertaining. Working fireplaces in the living room and private office create warm, inviting spaces, while the sunroom opens to the serene outdoor setting and swimming pool nestled in the landscape. The beautifully updated eat-in kitchen serves as the heart of the home, featuring brand new quartz countertops, a striking slab backsplash, and refined finishes - perfect for both intimate gatherings and larger entertaining. Recent improvements include new light fixtures, a refreshed primary bath, and freshly painted interiors, creating a move-in ready experience. Surrounded by Tokeneke's natural beauty, this exceptional offering is moments from Scott's Cove, Tokeneke School, the train, and downtown Darien's Corbin District. A rare opportunity to enjoy privacy, elegance, and the unparalleled Tokeneke lifestyle.
Sold for $3,205,000
$3,205,000
18 Winding Lane, Darien, CT 06820
4beds
3,972sqft
Single Family Residence
Built in 1963
1.4 Acres Lot
$3,267,900 Zestimate®
$807/sqft
$18,700 Estimated rent
Home value
$3,267,900
$2.94M - $3.63M
$18,700/mo
Zestimate® history
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$19,312/mo
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List your homeWhat's special
Exceptional natural lightEffortless flowFreshly painted interiorsBrand new quartz countertopsStriking slab backsplashRefreshed primary bathNew light fixtures
Zillow last checked:
Listing updated:
Listed by:
Tami Hanford Hughes (203)253-3104,
Houlihan Lawrence 203-655-8238
Bought with:
Janine Tienken, RES.0775247
Houlihan Lawrence
Source: Smart MLS,MLS#: 24155541
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Bedroom Suite, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 330 Square Feet
- Dimensions: 15 x 22
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
- Area: 187 Square Feet
- Dimensions: 17 x 11
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 12 x 14
Bedroom
- Features: Hardwood Floor
- Level: Main
- Area: 110 Square Feet
- Dimensions: 10 x 11
Dining room
- Features: Hardwood Floor
- Level: Main
- Area: 195 Square Feet
- Dimensions: 13 x 15
Great room
- Features: Skylight, High Ceilings, Cathedral Ceiling(s), Beamed Ceilings, Hardwood Floor
- Level: Main
- Area: 575 Square Feet
- Dimensions: 23 x 25
Kitchen
- Features: Remodeled, Breakfast Nook, Quartz Counters, Kitchen Island, Sliders, Hardwood Floor
- Level: Main
- Area: 475 Square Feet
- Dimensions: 19 x 25
Living room
- Features: Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 325 Square Feet
- Dimensions: 13 x 25
Office
- Features: Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 165 Square Feet
- Dimensions: 11 x 15
Sun room
- Features: Sliders, Tile Floor
- Level: Main
- Area: 117 Square Feet
- Dimensions: 13 x 9
Heating
- Hot Water, Oil
Cooling
- Central Air, Ductless
Appliances
- Included: Gas Range, Oven, Microwave, Range Hood, Refrigerator, Freezer, Washer, Dryer, Water Heater
- Laundry: Upper Level
Features
- Basement: Crawl Space,Unfinished
- Attic: Storage,Floored,Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 3,972
- Total interior livable area: 3,972 sqft
- Finished area above ground: 3,972
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 2
Features
- Patio & porch: Patio
- Exterior features: Rain Gutters
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground
Lot
- Size: 1.40 Acres
- Features: Wooded, Rocky, Cul-De-Sac, Landscaped
Details
- Parcel number: 108798
- Zoning: R-1
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1963
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available
Community & neighborhood
Security
- Security features: Security System
Location
- Region: Darien
- Subdivision: Tokeneke
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $1,249 annually
- Services included: Security, Maintenance Grounds, Snow Removal
Price history
| Date | Event | Price |
|---|---|---|
| 3/27/2026 | Sold | $3,205,000+9.6%$807/sqft |
Source:  Smart MLS #24155541 Report a problem | ||
| 3/5/2026 | Pending sale | $2,925,000$736/sqft |
Source: Smart MLS #24155541 Report a problem | ||
| 2/24/2026 | Listed for sale | $2,925,000+8.4%$736/sqft |
Source: Smart MLS #24155541 Report a problem | ||
| 9/20/2022 | Listing removed | -- |
Source: Smart MLS #170486337 Report a problem | ||
| 8/9/2022 | Price change | $2,699,000-5.3%$680/sqft |
Source: Smart MLS #170486337 Report a problem | ||
| 6/15/2022 | Price change | $2,849,000-5%$717/sqft |
Source: Smart MLS #170486337 Report a problem | ||
| 5/5/2022 | Listed for sale | $3,000,000+42.2%$755/sqft |
Source: Smart MLS #170486337 Report a problem | ||
| 1/15/2016 | Sold | $2,109,500-1.4%$531/sqft |
Source: Smart MLS #99119147 Report a problem | ||
| 9/29/2015 | Listed for sale | $2,139,000-6.8%$539/sqft |
Source: William Pitt Sotheby's International Realty Report a problem | ||
| 7/9/2015 | Listing removed | $2,295,000$578/sqft |
Source: William Raveis Real Estate #99090682 Report a problem | ||
| 6/13/2015 | Price change | $2,295,000-0.2%$578/sqft |
Source: William Raveis Real Estate #99090682 Report a problem | ||
| 4/23/2015 | Price change | $2,300,000-4%$579/sqft |
Source: William Raveis Real Estate #99090682 Report a problem | ||
| 1/22/2015 | Listed for sale | $2,395,000+195.7%$603/sqft |
Source: William Raveis Real Estate #99090682 Report a problem | ||
| 7/1/1987 | Sold | $810,000$204/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $29,997 +5.4% | $1,937,810 |
| 2024 | $28,466 +8.1% | $1,937,810 +29.6% |
| 2023 | $26,326 +2.2% | $1,494,920 |
| 2022 | $25,757 +2.3% | $1,494,920 |
| 2021 | $25,174 +3.1% | $1,494,920 |
| 2020 | $24,412 -0.8% | $1,494,920 |
| 2019 | $24,621 +8.3% | $1,494,920 +5.7% |
| 2018 | $22,733 -0.5% | $1,413,720 |
| 2017 | $22,846 +2.5% | $1,413,720 |
| 2016 | $22,294 +2.7% | $1,413,720 |
| 2015 | $21,701 +2.3% | $1,413,720 |
| 2014 | $21,220 -2.4% | $1,413,720 -14.4% |
| 2013 | $21,739 +3.9% | $1,650,670 |
| 2012 | $20,930 +3.9% | $1,650,670 |
| 2011 | $20,138 +3.9% | $1,650,670 |
| 2010 | $19,379 +3.3% | $1,650,670 |
| 2009 | $18,768 -4.5% | $1,650,670 +22.3% |
| 2008 | $19,645 +11.8% | $1,350,160 +6.6% |
| 2007 | $17,567 +3.5% | $1,266,580 |
| 2006 | $16,972 -28% | $1,266,580 -30% |
| 2005 | $23,558 +55.6% | $1,809,400 +42.9% |
| 2004 | $15,136 +56% | $1,266,580 +70.5% |
| 2003 | $9,704 -6.9% | $743,050 |
| 2001 | $10,418 +7.4% | $743,050 -30% |
| 2000 | $9,704 +4.7% | $1,061,500 +103% |
| 1999 | $9,264 | $522,810 |
Find assessor info on the county website
Neighborhood: Tokeneke
Nearby schools
GreatSchools rating
- 9/10Tokeneke Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 10/10Middlesex Middle SchoolGrades: 6-8Distance: 1.9 mi
- 10/10Darien High SchoolGrades: 9-12Distance: 1.9 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
- 18 Winding Lane
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