New Canaan, CT / 1 DAY ON MARKET

20 Gray Squirrel DriveNew Canaan, CT 06840

Asking price$1,995,000Active

Open house

  • Saturday, September 19, 20262:00 pm – 4:00 pm ET
  • Sunday, September 20, 20261:00 pm – 3:00 pm ET

Our Take

20 Gray Squirrel Drive is a four-bedroom Colonial set at the end of a cul-de-sac, with a traditional layout organized around everyday living and entertaining. The main level includes a living room with built-in bookshelves and window seating, a den, dining room, eat-in kitchen, breakfast nook, and family room with one of two first-floor fireplaces. Upstairs are a primary suite with a large bath and oversized walk-in closet, three additional bedrooms, and a full bath. A detached 2019 barn adds workshop and finished living space.

Estimated buyer rebate

Buy with Cress and Save $19,950 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 40% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24203948
Bedrooms
4
BathroomsBaths
2 full / 1 half
Square feet
3,530
Year built
1966
Acres
2.1
Property taxes
$20,440

July 2026-June 2027

What stands out

  • End-of-cul-de-sac setting
  • Living room with built-in bookshelves and window seating
  • Eat-in kitchen and breakfast nook flowing to patio
  • Family room with one of two first-floor fireplaces
  • Primary suite with oversized walk-in closet
  • Detached 2019 barn with workshop and finished living space
Read the full listing description

Privately set at the end of a quiet cul-de-sac, this classic Colonial offers exceptional privacy, beautifully proportioned living spaces and a one-of-a-kind detached barn on a level 2-acre lot. The 4-bedroom home features a warm, timeless floor plan designed for both everyday living and entertaining. An open foyer leads to an inviting living room with built-in bookshelves and window seating, while the cozy den is ideal for work or study. A dedicated dining room, eat-in kitchen and sun-filled breakfast nook flow seamlessly to the patio and private backyard. The family room is filled with natural light and anchored by one of two first-floor fireplaces. Upstairs, the spacious primary suite features a large bath and oversized walk-in closet, along with three additional bedrooms and a full bath. The lower level offers flexible space and future potential. The true bonus feature is the detached barn, built in 2019 with workshop and finished living space. From an entertaining space to artist's studio, home office, gardening retreat or workshop, the possibilities are endless. Together, the cul-se-sac location, private setting, traditional layout, plus barn create something truly special.

Schools

Elementary
South
Middle
Saxe Middle
High
New Canaan

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

Open Google Maps ↗

20 Gray Squirrel Drive, New Canaan, CT 06840

Price history

DateEventPrice
Originally listed$1,995,000

Intermediate price changes and previous listings may not be included.

Could this be your next home?

Let’s talk about the property—and what working with Cress could save you.

Inquire about this property →

*Estimate: $1,995,000 asking price × assumed 2.5% buyer-agent commission × 40% rebate = $19,950. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Compass Connecticut, LLC · (203) 423-3100

Robin Halsey

SmartMLS · Listing #24203948 · Active

Listing data checked: Sep 18, 2026, 7:04 AM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

For personal, noncommercial use to identify properties you may be interested in purchasing.