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14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
14 Upland Drive
VIEW PHOTOS
Courtesy of Compass Connecticut, LLC
$3,195,500

14 Upland Drive

4 Beds 5 Baths 4,113 Sq.Ft. 1.6 Acres

Description

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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Location

14 Upland Drive, Greenwich, CT 06831

Status

Sold

Date Sold

August 6, 2026

Property Amenities

Interior
Total Bedrooms: 4
Half Bathrooms: 1
Full Bathrooms: 4
Other Interior Features Eat-in Kitchen, Bookcases, Sep Shower, Pantry
Area & Lot
Total area 4,113 Sq.Ft.
Lot Area 1.6 Acres
Living area 4,113 Sq.Ft.
MLS® ID 124767
Year Built 1936
Middle School Western
Elementary School Glenville
Architecture Styles Colonial
Type Residential
Status Sold
Exterior
Air conditioning Central Air
Heat type Natural Gas, Forced Air
Water Source Public
Garage Space 2.0
Sewer Town Sewer
Parking Attached Garage
Lot Features Parklike
Roof Asphalt
Finance
Sales Price $3,195,500
Real Estate Tax $14,152 yearly

Greenwich

A little city with small-town appeal. Delightful amenities near stunning shores and quaint countryside.

Work With Us

We are a dedicated group of Greenwich natives. We have a deep passion for our hometown and enjoy everything the town offers its residents from the beach front to the backcountry. That is why we don’t find you just any home, we find you the right home.