10 Winding Ln Westport, CT, 06880

single family home
$ 3,550,000 For Sale Active Mar 31, 2026
  • 5 beds
  • 5 baths
  • 4,602 sq ft
  • 1 acre
  • 2003 year built
  • in ground pool
  • 2 cars garage

About the Home

Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an open-concept floor plan enhanced by timeless architectural details and modern upgrades. Sun-drenched living spaces on the main level include a gourmet kitchen, formal living room, dining area, family room, office, and a versatile pool cabana or fitness room-all seamlessly opening to an expansive patio for effortless indoor-outdoor living. Two first-floor ensuite bedrooms provide flexible accommodations. Upstairs, the luxurious primary offers a private retreat, complemented by a large playroom, laundry room, and two additional bedrooms with a shared bath-creating a versatile layout. The resort-style outdoor setting is equally impressive, featuring a gunite pool with spa, pergola, fire pit, outdoor grill area, vegetable garden, and a fully integrated lighting and sound system. Mature, century-old trees, curated specimen plantings, and extensive stonework create a private, park-like oasis. For the buyer seeking privacy while being near all the amenities that Westport has to offer, this extraordinary property combines classic elegance, modern amenities, and an unbeatable location.

Rooms & Interior

5 bedrooms beds
4 full + 1 half baths
4,602 square feet sq ft

Room Details

  • Family Room (Main Level) Fireplace, French Doors, Hardwood Floor
  • Bedroom (Main Level) Full Bath, Hardwood Floor
  • Bedroom (Main Level) Full Bath, Hardwood Floor
  • Rec/Play Room (Main Level) French Doors, Hardwood Floor
  • Kitchen (Main Level) Skylight, Vaulted Ceiling, Island, Pantry, Hardwood Floor
  • Living Room (Main Level) Fireplace, French Doors, Hardwood Floor
  • Primary Br Suite (Upper Level) Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood Floor
  • Bedroom (Upper Level) Hardwood Floor
  • Dining Room (Main Level) French Doors, Hardwood Floor
  • Office (Main Level) French Doors, Hardwood Floor
  • Bedroom (Upper Level) Wall/Wall Carpet
  • Rec/Play Room (Upper Level) Vaulted Ceiling, Hardwood Floor
  • Other Rooms Laundry room, Mud room

Home Features

Heating

  • Fireplaces: 2
  • Heating: hot water
  • Heat fuel type: oil, propane
  • Fuel tank: above ground

Cooling

  • Central air
  • Zoned

Interior Features

  • Audio system
  • Security system

Appliances

  • Cook top
  • Wall oven
  • Microwave
  • Refrigerator
  • Freezer
  • Dishwasher
  • Disposal
  • Washer
  • Dryer

Attic

  • Walk-in

Basement

  • Crawl space

Laundry

  • Location: 2nd floor

Energy Features

  • Programmable thermostat
  • Thermopane windows

Exterior Features

  • Shed
  • Gutters
  • Garden area
  • Lighting
  • Stone wall
  • French doors
  • Patio

Property Details

Parking

  • Garage spaces: 2
  • Attached garage

Swimming Pool

  • Gunite
  • Heated
  • Spa
  • In ground pool

Waterfront

  • Water community
  • Access
Waterfront Homes in Westport

Lot Details

  • Lot surface: 1 acres
  • Fence - full
  • Level lot

Utilities

  • Water: public water connected
  • Sewage: septic

Near-by Amenities

  • Golf course
  • Health club
  • Library
  • Park
  • Shopping/mall
  • Tennis courts

Construction Details

Style
cape cod, colonial

Construction year
2003

Exterior Siding
shingle, stone, wood

Foundation
concrete

Roof
asphalt shingle


Area & Town

This home is located in Old Hill neighborhood, in the town of Westport.

Finance & Listing Info

Status Active
Listing date March 31, 2026
List price $ 3,550,000
Current price $ 3,550,000
Tax amount $ 25,653
Tax year july 2025-june 2026
MLS ID #24163168
List Agent Susan Lieberman
Co-List Agent Justine Fink
List Office The Riverside Realty Group
Co-List Office the riverside realty group

10 Winding Lane Home Photos

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