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A rare opportunity in one of Greenwich's most coveted in-town settings, 21 Calhoun Drive combines the timeless presence and character of a classic Greenwich estate with exceptional privacy, generous scale and remarkable potential. Set amid mature landscaping on approximately 1.8 acres in a one-acre zone, the property offers nearly twice the typical lot size while remaining just moments from the heart of Greenwich. Inside, gracious entertaining rooms, comfortable everyday living spaces and distinctive architectural details create a home with warmth, character and a sense of permanence rarely replicated today. A newly renovated kitchen brings a fresh, modern sensibility to the residence and serves as a beautiful centerpiece for daily living and entertaining. A private wellness retreat, complete with an indoor pool and dedicated fitness space, brings resort-style amenities into the comfort and privacy of home. Beyond the main residence, the expansive grounds offer an exceptional opportunity to further enhance the estate. Fully permitted plans provide the option to add a Cottage, along with the potential for a pickleball or tennis court an increasingly rare offering this close to town. With its substantial acreage, established landscaping, private wellness amenities and extraordinary flexibility for the future, this is a unique opportunity to enjoy a private estate setting without sacrificing the convenience of in-town Greenwich living.

5 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24205524 MLS

A rare opportunity in one of Greenwich's most coveted in-town settings, 21 Calhoun Drive combines the timeless presence and character of a classic Greenwich estate with exceptional privacy, generous scale and remarkable potential. Set amid mature landscaping on approximately 1.8 acres in a one-acre zone, the property offers nearly twice the typical lot size while remaining just moments from the heart of Greenwich. Inside, gracious entertaining rooms, comfortable everyday living spaces and distinctive architectural details create a home with warmth, character and a sense of permanence rarely replicated today. A newly renovated kitchen brings a fresh, modern sensibility to the residence and serves as a beautiful centerpiece for daily living and entertaining. A private wellness retreat, complete with an indoor pool and dedicated fitness space, brings resort-style amenities into the comfort and privacy of home. Beyond the main residence, the expansive grounds offer an exceptional opportunity to further enhance the estate. Fully permitted plans provide the option to add a Cottage, along with the potential for a pickleball or tennis court an increasingly rare offering this close to town. With its substantial acreage, established landscaping, private wellness amenities and extraordinary flexibility for the future, this is a unique opportunity to enjoy a private estate setting without sacrificing the convenience of in-town Greenwich living.

21 Calhoun Dr, Greenwich

A Greenwich classic, this distinguished five-bedroom residence combines timeless architecture, exceptional craftsmanship, and grand-scale rooms designed for both entertaining and everyday living. Perched high above sweeping, beautifully landscaped grounds, the home enjoys a commanding setting with privacy, mature plantings, and expansive westerly views across the property. A slate roof, custom millwork, multiple fireplaces, and graciously proportioned interiors further reflect the home's enduring character. Elegant formal living and dining rooms are complemented by a Christopher Peacock kitchen with adjoining breakfast room, a comfortable family room, and a library or private office. Upstairs, the spacious primary suite is joined by three additional bedrooms, two of which are en suite. A fifth bedroom and flexible living space on the lower level provide additional accommodations. Expansive terraces extend the living spaces outdoors, overlooking the sweeping grounds and putting green, while a circular drive creates an impressive approach. A rare combination of scale, privacy, and setting, just minutes from central Greenwich.

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24202628 MLS

A Greenwich classic, this distinguished five-bedroom residence combines timeless architecture, exceptional craftsmanship, and grand-scale rooms designed for both entertaining and everyday living. Perched high above sweeping, beautifully landscaped grounds, the home enjoys a commanding setting with privacy, mature plantings, and expansive westerly views across the property. A slate roof, custom millwork, multiple fireplaces, and graciously proportioned interiors further reflect the home's enduring character. Elegant formal living and dining rooms are complemented by a Christopher Peacock kitchen with adjoining breakfast room, a comfortable family room, and a library or private office. Upstairs, the spacious primary suite is joined by three additional bedrooms, two of which are en suite. A fifth bedroom and flexible living space on the lower level provide additional accommodations. Expansive terraces extend the living spaces outdoors, overlooking the sweeping grounds and putting green, while a circular drive creates an impressive approach. A rare combination of scale, privacy, and setting, just minutes from central Greenwich.

74 Glenville Rd, Greenwich

Impeccably maintained, stunning classic colonial, tucked away on a private road in one of Greenwich's most sought-after enclaves. A combination of traditional New England architecture with spacious interiors designed for comfortable everyday living and entertaining. Enter in through a magnificent, sun filled double height entry. Generously scaled rooms, hardwood floors, multiple entertaining areas and an open floor plan filled with natural light. Large kitchen and family room. Primary suite, one ensuite bedroom and one Jack and Jill with double sink. Finished third floor for office, den, or guests, plus an unfinished attic for storage. Fabulous finished lower level which can be used as an additional family room, gym, or playroom. Large 2 car attached garage. Expansive lawns, mature landscaping, and a magnificent pool offer a private spa like setting that enhances the home's retreat-like atmosphere Quiet, wooded surroundings and elegant curb appeal. A balance of privacy and convenience, with access to top-rated Greenwich schools, country clubs, equestrian properties, and commuter routes to New York City. Minutes to downtown Greenwich, shops and restaurants, beaches and parks!

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24177801 MLS

Impeccably maintained, stunning classic colonial, tucked away on a private road in one of Greenwich's most sought-after enclaves. A combination of traditional New England architecture with spacious interiors designed for comfortable everyday living and entertaining. Enter in through a magnificent, sun filled double height entry. Generously scaled rooms, hardwood floors, multiple entertaining areas and an open floor plan filled with natural light. Large kitchen and family room. Primary suite, one ensuite bedroom and one Jack and Jill with double sink. Finished third floor for office, den, or guests, plus an unfinished attic for storage. Fabulous finished lower level which can be used as an additional family room, gym, or playroom. Large 2 car attached garage. Expansive lawns, mature landscaping, and a magnificent pool offer a private spa like setting that enhances the home's retreat-like atmosphere Quiet, wooded surroundings and elegant curb appeal. A balance of privacy and convenience, with access to top-rated Greenwich schools, country clubs, equestrian properties, and commuter routes to New York City. Minutes to downtown Greenwich, shops and restaurants, beaches and parks!

5 Willow Run Rd, Greenwich

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sun room, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

6 Beds ⋅ 10 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24177074 MLS

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sun room, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

55 Calhoun Dr, Greenwich

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