10 Winding Ln

Off Market

10 Winding Ln

Westport CT 06880

4602 sq. ft.

1 ac.

Single-Family

Last sold for $3,600,000

Susan Lieberman, last sold this property on 08 June 2026 after 67 days on market.

Overview

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.

Features

5 bedrooms

5 bathrooms

2 carspaces

2 garage spaces

4602 sq. ft. floor area

1 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Westport over the last 12 months, the estimated median property value of 10 Winding Ln is $2.9m.

Median value

$2.9m

Estimated value range

$840k - $24.21m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Westport. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 10 Winding Ln

2026

Sold

$3,600,000

08 Jun 2026 by Susan Lieberman, of The Riverside Realty Group

2017

Sold

$2,150,000

15 May 2017 by Susan Lieberman, of The Riverside Realty Group

Happy sellers in Westport

<50%

Less than 50% of sellers in Westport reported that their sale price either exceeded or met their price expectations.

Westport stands out as a desirable community for sellers, consistently delivering great customer service and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Westport over the last 12 months.

Local market activity for 5 bedroom single-family properties in Westport

In the last 12 months, 81 five-bedroom single-family properties similar to 10 Winding Ln, have been sold.

This represents a 18% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Westport for a market analysis.

Hyleri Katzenberg

at Compass Connecticut, LLC

(66 reviews)

Get a market analysis

Judy Michaelis

at Coldwell Banker Realty

(74 reviews)

Get a market analysis

Tony Salerno

(24 reviews)

Get a market analysis

Jessica Kolomondos

at RE/MAX Heritage

(6 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Westport

Hyleri Katzenberg

Sellers who recommend Hyleri Katzenberg have praised them for being local expert, responsive, patient, supportive, great negotiation, reliable, and dedicated

5 (66 reviews)
5 Reviews in Westport
5 Sales in Westport

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Judy Michaelis

Sellers who recommend Judy Michaelis have praised them for being local expert, responsive, supportive, clear communication, reliable, great negotiation, and strategic