Recently Listed Open House 4/4 1pm - 3pm
10 Winding Lane
Westport, CT, 06880 $ 3,550,000
Bedrooms5 Baths4.1 Sq 4,602 Monthly Estimate*
$ 21,858
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
FeaturesGeneralZoning 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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InteriorCooling System Central Air Zoned
Total Rooms 12
Basement Description Crawl Space
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ExteriorWater Source Public Water Connected
Lot Description Fence - Full Level Lot
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* Excluded FeaturesList BySusan LiebermanListing Agent
The Riverside Realty GroupBroker
suelieberman@yahoo.comEmail
Affordability Calculator
- 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.
Learn more about how to save NearbySingle family listings in Westport, CT
Average List Price $4,097,081
Percent of Sale Price 15%
About Westport, CT 26,742 Population
4% Since 2002
$ 169,979 Median Income
48.33 Median Age
40% Households with Children
Trends Information provided by ATTOM Data Solutions.
1233224 Elementary School
1967866 Middle School
Staples High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 3/31/2026 | $3,550,000 | | Listed Price |