10 Winding Lane Westport, CT $ 3,550,000
10 Winding Lane
$ 3,550,000
Recently Listed
Open House 4/4 1pm - 3pm
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10 Winding Lane

Westport, CT, 06880
$ 3,550,000
Bedrooms5 Baths4.1 Sq 4,602

Monthly Estimate*

$ 21,858

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Single Family Home for sale in Westport, CT

for $3,550,000 with 5 bedrooms and 4 full baths, 1 half bath. This 4,602 square foot home was built in 2003 on a lot size of 1.

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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Open House

4/4/2026 1:00 PM - 3:00 PM
10 Winding Lane Westport, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 3,550,000

Bedrooms

5

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 25,653

Style

Lot Size

1

Year Built

2003

Town/City

Westport

MLS | Web ID

24163168

Features
General
Zoning AA
Neighborhood Old Hill
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 1
Directions Stonybrook or Old Hill to Winding Lane.
High School Staples
City Westport
Elementary School Kings Hwy
Sq Ft Total 4602
DOM 0
Year Built 2003
Exclusions wall mounted tv's gas grill
Style Cape Cod Colonial
Year Built Source Owner
Pool Description Gunite Heated Spa In Ground Pool
Energy Features Programmable Thermostat Thermopane Windows
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Interior
Cooling System Central Air Zoned
Total Rooms 12
Basement Description Crawl Space
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Exterior
Water Source Public Water Connected
Lot Description Fence - Full Level Lot
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* Excluded Features
List By
Susan Lieberman

Listing Agent

The Riverside Realty Group

Broker

suelieberman@yahoo.com

Email

Affordability Calculator

$23,996
Per Month
91%
9%
0%
Monthly Principal & Interest
$21,858
Monthly Property Taxes
$2,138
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
1233224 Elementary School
1967866 Middle School
Staples High School High School
Pricing History
DatePricePrice ChangeDescription
3/31/2026$3,550,000 Listed Price

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10 Winding Lane, Westport, CT, 06880 is a Single Family Home for sale at $3,550,000 with 4,602 sqft and a lot size of 1. 10 Winding Lane has 5 bedrooms, 4.1 baths, and was built in 2003. The property's zip code is 06880 which is in Westport, CT