Re-built in 2008 using the highest level of craftsmanship, located in the desirable Calhoun Drive Association, this residence sits gracefully elevated, offering sweeping views of expansive lawns with mature specimen trees. Step through bespoke double mahogany doors into a grand foyer featuring tall ceilings, hardwood floors and exquisite millwork throughout. Designed for both gracious everyday living and stylish entertaining, the home offers a seamless flow between generously proportioned spaces. A sun-drenched sunroom, family room, and a kitchen with adjoining breakfast area all open onto an expansive terrace—perfect for indoor-outdoor living and dining. There are multiple office spaces and incredible storage throughout. Upstairs, the luxurious primary suite offers a serene retreat with sitting room, private terrace, walk in closets and two baths. There are five additional sun-filled double bedrooms each with its own Waterworks bathroom. An additional private guest suite provides added comfort and privacy. The walk-out lower level is designed for recreation and relaxation, featuring a family room, gym, wine cellar, and a spacious entertainment area including kitchenette that opens to a covered patio. 55 Calhoun also includes a charming two-story original carriage house currently used for additional garaging (five in total) adding both character and versatility to the property. This distinguished and private home is a rare opportunity to enjoy refined living with close proximity to all the town of Greenwich, Connecticut has to offer.