18 Winding Lane, Darien, CT 06820
Home value
$3,325,500
$2.99M - $3.69M
$18,700/mo
Owner options
$18,700/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$18,700/mo
Rent Zestimate®
$19,312/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$19,312/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Tami Hanford Hughes (203)253-3104,
Houlihan Lawrence 203-655-8238
Janine Tienken, RES.0775247
Houlihan Lawrence
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: 1.4 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 & HOA
Community
- Security: Security System
- Subdivision: Tokeneke
HOA
- Has HOA: Yes
- Services included: Security, Maintenance Grounds, Snow Removal
- HOA fee: $1,249 annually
Location
- Region: Darien
Financial & listing details
- Price per square foot: $807/sqft
- Tax assessed value: $1,937,810
- Annual tax amount: $29,997
- Date on market: 2/24/2026
- Exclusions: No Exclusions
Price history
| Date | Event | Price |
|---|---|---|
| 3/27/2026 | Sold | $3,205,000+9.6%$807/sqft |
Source: | ||
| 3/5/2026 | Pending sale | $2,925,000$736/sqft |
Source: | ||
| 2/24/2026 | Listed for sale | $2,925,000+8.4%$736/sqft |
Source: | ||
| 9/20/2022 | Listing removed | -- |
Source: | ||
| 8/9/2022 | Price change | $2,699,000-5.3%$680/sqft |
Source: | ||
| 6/15/2022 | Price change | $2,849,000-5%$717/sqft |
Source: | ||
| 5/5/2022 | Listed for sale | $3,000,000+42.2%$755/sqft |
Source: | ||
| 1/15/2016 | Sold | $2,109,500-1.4%$531/sqft |
Source: | ||
| 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 |
Neighborhood: Tokeneke
Nearby homes
- $3,714,9004 bd4 ba3.6k sqft14 Winding Ln, Darien, CT 06820Off Market

- $3,593,5004 bd4 ba4.1k sqft22 Winding Ln, Darien, CT 06820Off Market
- $3,053,7004 bd3 ba2.8k sqft21 Winding Ln, Darien, CT 06820Off Market

- $3,049,4005 bd4 ba3.4k sqft22 Arrowhead Way, Darien, CT 06820Off Market

- $3,611,8504 bd4 ba3.7k sqft10 Winding Ln, Darien, CT 06820Sold
- $4,801,9004 bd5 ba5.2k sqft19 Winding Ln, Darien, CT 06820Off Market
- $3,533,8005 bd5 ba4.7k sqft26 Winding Ln, Darien, CT 06820Off Market
- $3,678,3005 bd3 ba4.4k sqft20 Arrowhead Way, Darien, CT 06820Off Market
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.
Sell for more on Zillow
- Connecticut
- Fairfield County
- Darien
- 06820
- Tokeneke
- 18 Winding Lane