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14 Upland DriveGreenwich, CT 06831

For Sale

$3,195,000

Smart Buyer Rebate $31,950

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.

Listed by Roseann Benedict

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License #RES.0783145

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Compass Connecticut, LLC

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203-979-9104

Last updated April 26, 2026

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Source: FlexMLS #124767

Listing Facts

  • TypeSingle-family
  • NeighborhoodPemberwick
  • Bedrooms4
  • Bathrooms4.5
  • Days on Prevu10
  • Taxes$16,683/year
  • Size4,113 sqft
  • Price per sqft$777

Amenities

  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

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Listing History

04/20/2026
Listed by Compass Connecticut, LLC
$3,195,000

Property Details for 14 Upland Drive

Exterior

Construction

  • Roof: Asphalt
  • Year Built: 1936
  • Architectural Style: Colonial
  • Construction Materials: Brick

Features

  • Patio And Porch Features: Terrace

Measurements

  • Building Area Total: 4,113
  • Lot Features: Parklike
  • Lot Size Acres: 1.60
  • Lot Size Area: 1
  • Lot Size Square Feet: 69,696
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 07-1215/S
  • Tax Annual Amount: $16,683.00
  • Tax Assessed Value: $1,349,880.00

Interior

Features

  • Fireplace: Yes
  • Fireplaces Total: 2
  • Interior Features: Eat-in Kitchen, Bookcases, Sep Shower, Pantry

Rooms

  • Basement: Partial, Unfinished
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4

Other

General

  • Exclusions: Call LB

Location

  • City Region: South Parkway

Parking

Parking

  • Garage Spaces: 2
  • Parking Features: Attached Garage

Schools

Elementary School

  • Elementary School: Glenville

Middle or Junior School

  • Middle Or Junior School: Western

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Natural Gas, Forced Air
  • Has Heating: Yes
  • Sewer: Town Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 4.5 bathrooms in this single-family home at 14 Upland Drive.

What schools are nearby to 14 Upland Drive?

Nearby schools include the Glenville Elementary School and Western Middle School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 14 Upland Drive.

What are the annual taxes for 14 Upland Drive?

Annual taxes for this single-family home are estimated at $16,683.

How does 14 Upland Drive compare to other single-family homes in Pemberwick?

This single-family home is listed 20% above the average price for single-family homes in Pemberwick and has been on the market for 67 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 4,113 sqft.

14 Upland Drive is a 4-bedroom, 4.5-bath single-family home for sale in Greenwich CT 06831. On Prevu for 10 days at $3,195,000. This home features 4,113 square feet of living space, located in Pemberwick. The median listing price for single-family homes in this area is $1,997,500. Nearby schools include Glenville Elementary School and Western Middle School. The home offers private outdoor space, air conditioning, parking, and washer/dryer. Browse more single-family home listings in Fairfield County.

Based on information from Greenwich Multiple Listing Service, Inc. and/or other sources. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by Prevu or the MLS. Information is provided exclusively for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.