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$3,205,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,972 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 18 Winding Ln

General

  • Sold For: $3,205,000
  • HOA FEE: $104/month
  • HOA FEE FREQ.: Annually
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24155541
  • Added to Site: 49 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Bedroom Suite, Full Bath, Walk-In Closet, Hardwood Floor, 22 x 15, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 11 x 10, Main
  • Bedroom 2: Bedroom - Full Bath, Hardwood Floor, 11 x 17, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, 14 x 12, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, French Doors, Hardwood Floor, 25 x 13, Main
  • Great Room: Great Room - Skylight, 9 ft+ Ceilings, Cathedral Ceiling, Beams, Hardwood Floor, 25 x 23, Main
  • Kitchen: Kitchen - Remodeled, Breakfast Nook, Quartz Counters, Island, Sliders, Hardwood Floor, 25 x 19, Main
  • Dining Room: Dining Room - Hardwood Floor, 15 x 13, Main
  • Office: Office - Fireplace, French Doors, Hardwood Floor, 15 x 11, Main
  • Laundry: Upper Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, In Ground Pool

Exterior

  • Exterior Features: Gutters, Patio
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Tokeneke
  • Driving Directions: Locust Hill to Arrowhead Way to Winding Lane. House is on the right

School Information

  • Elementary School: Tokeneke
  • Middle School: Middlesex
  • High School: Darien

Community

  • Community Name: Tokeneke
  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Security Service, Grounds Maintenance, Snow Removal

Heating & Cooling

  • Cooling Type: Central Air, Ductless
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Crawl Space, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,972
  • Above Ground: 3,972 Sq. Ft.
  • Year Built: 1963

Lot Features

  • Lot Size (Acres): 1.4
  • Zoning: R-1
  • Lot Description: Treed, Rocky, On Cul-De-Sac, Professionally Landscaped

Financial Considerations

  • Association Fee: $1,249
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $1,937,810
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: No Exclusions
  • Property ID: 108798

Listed by Houlihan Lawrence, Tami Hanford Hughes
Sold by Houlihan Lawrence, Janine Tienken

Listing agent

— 18 Winding Ln —

  • Tami Hanford Hughes

    Houlihan Lawrence

Agent Contact: (203) 253-3104 Office Contact: (203) 655-8238

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 18 Winding Ln

School District:Darien School District
NameGradesDistance
Tokeneke Elementary School
7 Old Farm Road, Darien, CT 06820
K-50.5 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-81.8 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-121.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 18 Winding Ln

Date
Details
Price
Change
Source
3/27/2026
Sold
$3,205,000
9.57%
MLS
2/24/2026
Listed
$2,925,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Houlihan Lawrence, Tami Hanford Hughes
Sold by Houlihan Lawrence, Janine Tienken

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18 Winding Lane, Darien, CT 06820 (MLS# 24155541) is a Single Family property that was sold at $3,205,000 on March 27, 2026. Want to learn more about 18 Winding Lane? Do you have questions about finding other Single Family real estate for sale in Tokeneke? You can browse all Tokeneke real estate or contact a Coldwell Banker agent to request more information.