14 Upland Drive

Greenwich, CT 06831 Directions
$3,195,000
  • 4Bed
  • 4/1Baths
  • 1.6Acres
  • 1936Built
  • GlenvilleElementary

Property Highlights

  • Mid. School: Western
  • Neighborhood: 3 - Greenwich
  • Days on Market: 19
  • MLS: 124767
  • Listing Pending

Property Highlights

  • Mid. School: Western
  • Neighborhood: 3 - Greenwich
  • Days on Market: 19
  • MLS: 124767
  • Listing Pending

Set on 1.6 beautifully landscaped acres in a coveted Greenwich location, this exceptional four-bedroom residence offers space, flexibility, and timeless appeal. A dramatic two-story entry with a sweeping balcony sets the tone, leading into an oversized step-down living room with a fireplace, abundant natural light, and doors that open seamlessly to a patio perfect for indoor-outdoor living and entertaining. The home features four bedrooms, including a gracious primary suite complete with a private makeup enclave and a walk-in closet as well as a well-appointed guest suite with its own sitting room - ideal for visitors or extended stays....

Property Highlights

  • Mid. School: Western
  • Neighborhood: 3 - Greenwich
  • Days on Market: 19
  • MLS: 124767
  • Listing Pending

Set on 1.6 beautifully landscaped acres in a coveted Greenwich location, this exceptional four-bedroom residence offers space, flexibility, and timeless appeal. A dramatic two-story entry with a sweeping balcony sets the tone, leading into an oversized step-down living room with a fireplace, abundant natural light, and doors that open seamlessly to a patio perfect for indoor-outdoor living and entertaining. The home features four bedrooms, including a gracious primary suite complete with a private makeup enclave and a walk-in closet as well as a well-appointed guest suite with its own sitting room - ideal for visitors or extended stays. One of the bedrooms is currently configured as a home office, offering versatility for today's lifestyle. At the heart of the home, the eat-in kitchen with fireplace flows effortlessly into the dining area, with additional access to the outdoor patio. An attractive, elegant library provides the perfect retreat for quiet moments. A standout feature is the separate studio space with its own entrance, full bathroom, kitchen corner, and garage access--ideal for guests, an au pair, creative workspace, or private home office. This property offers privacy, tranquility, and the rare opportunity to enjoy a true Greenwich lifestyle. Easy 20 min. walk to the train station.

Set on 1.6 beautifully landscaped acres in a coveted Greenwich location, this exceptional four-bedroom residence offers space, flexibility, and timeless appeal. A dramatic two-story entry with a sweeping balcony sets the tone, leading into an oversized step-down living room with a fireplace, abundant natural light, and doors that open seamlessly to a patio perfect for indoor-outdoor living and entertaining. The home features four bedrooms, including a gracious primary suite complete with a private makeup enclave and a walk-in closet as well as a well-appointed guest suite with its own sitting room - ideal for visitors or extended stays. One of the bedrooms is currently configured as a home office, offering versatility for today's lifestyle. At the heart of the home, the eat-in kitchen with fireplace flows effortlessly into the dining area, with additional access to the outdoor patio. An attractive, elegant library provides the perfect retreat for quiet moments. A standout feature is the separate studio space with its own entrance, full bathroom, kitchen corner, and garage access--ideal for guests, an au pair, creative workspace, or private home office. This property offers privacy, tranquility, and the rare opportunity to enjoy a true Greenwich lifestyle. Easy 20 min. walk to the train station.

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  • Additional Information
    • Basement Description: Partial, Unfinished
    • Elementary School: Glenville
    • Middle School: Western
    • On Market Date: 2026-04-20
    • Style: Colonial
    • Tax Amount: $16,683
    • Type: Residential
    • Year Built: 1936
  • Interior/Exterior Features
    • Beds: 4
    • Construction Materials: Brick
    • Cooling: Central Air
    • Exterior Features: Terrace
    • Full Baths: 4
    • Heat: Natural Gas, Forced Air
    • Interior Features: Eat-in Kitchen, Bookcases, Pantry
    • Roof: Asphalt
William Pitt / Julia B. Fee Sotheby's International Realty

New Canaan Brokerage

26 Cherry Street
New Canaan, CT 06840

Information provided by the Greenwich Multiple Listing Service, Inc. © 2026. Listing Courtesy of Roseann Benedict of Compass Connecticut, LLC. Data is updated as of 12:38 PM on 05/08/2026

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