10 Winding Lane

Westport, CT 06880

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.

Listing courtesy of Susan Lieberman of The Riverside Realty Group Office Phone: (203) 226-8300 Broker Contact: (203) 858-9411



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Last checked: 2026-04-01 08:37 PM UTC.