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$3,550,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,602 Sq. Ft.
  • 2 Car Garage
  • Updated 3 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 4/4 1:00 PM - 3:00 PM

10 Winding Lane,Westport, CT 06880

10 Winding LaneWestportCT06880

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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.

Full Property Details for 10 Winding Ln

General

  • Price: $3,550,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24163168
  • Updated: Today (4/2/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 12
  • Rooms/Areas: Laundry Room, Mud Room
  • Interior Features: Audio System, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Cook Top, Wall Oven, Microwave, Refrigerator, Freezer, Dishwasher, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood, Upper
  • Bedroom 1: Bedroom - Full Bath, Hardwood Floor, Main
  • Bedroom 2: Bedroom - Full Bath, Hardwood Floor, Main
  • Bedroom 3: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 4: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, French Doors, Hardwood Floor, Main
  • Family Room: Family Room - Fireplace, French Doors, Hardwood Floor, Main
  • Kitchen: Kitchen - Skylight, Vaulted Ceiling, Island, Pantry, Hardwood Floor, Main
  • Dining Room: Dining Room - French Doors, Hardwood Floor, Main
  • Office: Office - French Doors, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - French Doors, Hardwood Floor, Main
  • Rec Room: French Doors, Hardwood Floor, Main

Additional Information

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

Exterior

  • Exterior Features: Shed, Gutters, Garden Area, Lighting, Stone Wall, French Doors, Patio
  • Color: Sage

Parking

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

Location

  • County: Fairfield
  • Neighborhood: Old Hill
  • Driving Directions: Stonybrook or Old Hill to Winding Lane.

School Information

  • Elementary School: Kings Hwy
  • Middle School: Coleytown
  • High School: Staples

Community

  • Community Name: Old Hill

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Water, Oil, Propane
  • Heating Fuel: Oil, Propane
  • Water Heater: Other

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod, Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Shingle, Stone, Wood
  • Basement Desc.: Crawl Space
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,602
  • Above Ground: 4,602 Sq. Ft.
  • Year Built: 2003

Lot Features

  • Lot Size (Acres): 1
  • Zoning: AA
  • Lot Description: Fence - Full, Level Lot

Water Features

  • Water Front Desc.: Water Community, Access

Green Features

  • Energy Features: Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $1,360,200
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: wall mounted tv's, gas grill
  • Property ID: 413860

Listed by The Riverside Realty Group, Sue Lieberman and Justine Fink Team, Susan Lieberman and The Riverside Realty Group, Sue Lieberman and Justine Fink Team, Justine Fink

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Listing agents

— 10 Winding Ln —

  • Susan Lieberman

    The Riverside Realty Group

  • Justine Fink

    The Riverside Realty Group

Agent Contact: (203) 858-9411 Office Contact: (203) 226-8300

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 10 Winding Ln

School District:Westport School District
NameGradesDistance
King's Highway Elementary School
125 Post Road West, Westport, CT 06880
K-50.7 mi
Coleytown Middle School
255 North Avenue, Westport, CT 06880
6-82.6 mi
Staples High School
70 North Avenue, Westport, CT 06880
9-122.5 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 10 Winding Ln Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/02/2026
Listed
$3,550,000
184%
MLS
5/15/2017
Sold
$1,250,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 10 Winding Ln

Year
Property Taxes
Change
Tax Assessment
Change
2024
$25,653
1%
$1,360,200
—
2023
$25,327
1%
$1,360,200
—
2023
$24,960
2%
$1,360,200
—
2022
$24,579
—
$1,360,200
—
2021
$24,579
-1%
$1,360,200
-8%
2020
$24,736
-1%
$1,480,300
—
2019
$24,958
—
$1,480,300
—
2018
$24,958
—
$1,480,300
—
2017
$24,958
—
$1,480,300
—
2016
$24,958
-3%
$1,480,300
4%
2015
$25,715
1%
$1,421,500
—
2014
$25,502
-1%
$1,421,500
—
2011
$25,687
—
$1,421,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by The Riverside Realty Group, Sue Lieberman and Justine Fink Team, Susan Lieberman and The Riverside Realty Group, Sue Lieberman and Justine Fink Team, Justine Fink

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10 Winding Lane, Westport, CT 06880 (MLS# 24163168) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 10 Winding Lane is currently listed for $3,550,000 and was received on April 02, 2026. Want to learn more about 10 Winding Lane? Do you have questions about finding other Single Family real estate for sale in Westport? You can browse all Westport real estate or contact a Coldwell Banker agent to request more information.

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