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10 Winding Lane

Westport, CT 06880
  • $3,550,000
  • STATUS: Active Under Contract
  • ON SITE: 50 Days
  • MLS #: 24163168
Under Contract
UPDATED: 74 min ago
$3,550,000
  • 5
    BEDS
  • 1
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 4,602
    SQFT
  • $771
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2003
County:
Area:

School Information

Elementary School:
Middle School:
High School:

Description

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.

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-05-21T11:10:24.647.
www.lowerhudsonvalleyproperties.com/homes/174626264
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10 Winding Lane Westport, CT 06880

  • Price: $3,550,000
  • Status: Active Under Contract
  • On Site: 50 Days
  • Updated: 74 min ago
  • MLS #: 24163168
5
Beds
4
Baths
1
½ Baths
1
Acres
4,602
SQFT
$771
$/SQFT
2003
Built
Neighborhood:
Old Hill
County:
Fairfield
Area:
Westport
Elementary School:
Kings Hwy
Middle School:
Coleytown
High School:
Staples
Property Description
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.
Exterior Features

Color Sage Direct Waterfront YN No Exterior Features ShedGuttersGarden AreaLightingStone WallFrench DoorsPatio Exterior Siding ShingleStoneWood Garage And Parking Attached Garage Lot Description Fence - FullLevel Lot Nearby Amenities Golf CourseHealth ClubLibraryParkShopping/MallTennis Courts Pool Description GuniteHeatedSpaIn Ground Pool Roof Information Asphalt Shingle Style Cape CodColonial Swimming Pool YN Yes Waterfront Description Water CommunityAccess

Interior Features

Appliances Included Cook TopWall OvenMicrowaveRefrigeratorFreezerDishwasherDisposalWasherDryer Attic Description Walk-In Attic YN Yes Basement Description Crawl Space Cooling System Central AirZoned Fireplaces Total 2 Heat Type Hot Water Interior Features Audio SystemSecurity System Laundry Room Location 2nd Floor Living Area SQFTPer Public Record 4602 Rooms Family Room (Main Level FireplaceFrench DoorsHardwood Floor) Bedroom (Main Level Full BathHardwood Floor) Bedroom (Main Level Full BathHardwood Floor) Rec/Play Room (Main Level French DoorsHardwood Floor) Kitchen (Main Level SkylightVaulted CeilingIslandPantryHardwood Floor) Living Room (Main Level FireplaceFrench DoorsHardwood Floor) Primary BR Suite (Upper Level Vaulted CeilingFull BathWalk-In ClosetHardwood Floor) Bedroom (Upper Level Hardwood Floor) Dining Room Rooms Additional Laundry RoomMud Room Sq Ft Est Heated Above Grade 4602 Total Rooms 12

Property Features

Agent Owner YN No Bank Owned Property No Energy Features Programmable ThermostatThermopane Windows Exclusions wall mounted tv'sgas grill Financing Used Cash Foundation Type Concrete Fuel Tank Location Above Ground Heat Fuel Type OilPropane Home Owners Assocation No Home Warranty Offered YN No Hot Water Description Other New Construction Type No/Resale Potential Short Sale No Radon Mitigation Air YN No Radon Mitigation Water YN No Sewage System Septic Tax Year July 2025-June 2026 Under Agreement Yn No Water Source Public Water Connected Zoning AA

Listing information © 2026 Smart MLS
Listing provided courtesy of Susan Lieberman of The Riverside Realty Group: (203) 226-8300.


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-05-21T11:10:24.647.
 
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