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$1,995,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,530 Sq. Ft.
  • 2 Car Garage
  • Updated 20 hours ago

Next open house:

Open House: 2:00 PM - 4:00 PM

Saturday 9/19 2:00 PM - 4:00 PM

20 Gray Squirrel Drive,New Canaan, CT 06840

20 Gray Squirrel DriveNew CanaanCT06840

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Join us at 20 Gray Squirrel Drive on:

  • Open House: 1:00 PM - 3:00 PM

    Sunday 9/20 1:00 PM - 3:00 PM

    20 Gray Squirrel Drive,New Canaan, CT 06840
    20 Gray Squirrel DriveNew CanaanCT06840
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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.

Full Property Details for 20 Gray Squirrel Dr

General

  • Price: $1,995,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24203948
  • Updated: 9/17/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Bonus Room, Exercise Room, Laundry Room, Mud Room, Workshop
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Gas Cooktop, Wall Oven, Microwave, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Full Bath, Stall Shower, Whirlpool Tub, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Hardwood Floor, Main
  • Family Room: Family Room - Fireplace, Hardwood Floor, Main
  • Kitchen: Kitchen - Breakfast Bar, Built-Ins, Dining Area, Wet Bar, Island, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Den: Den - Fireplace, Hardwood Floor, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Barn, Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Driving Directions: 20 Gray Squirrel Drive, New Canaan

School Information

  • Elementary School: South
  • Middle School: Saxe Middle
  • High School: New Canaan

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Shingle, Wood
  • Basement Desc.: Full, Sump Pump, Storage, Garage Access, Interior Access, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,530
  • Above Ground: 3,212 Sq. Ft.
  • Below Ground: 318 Sq. Ft.
  • Year Built: 1966

Lot Features

  • Lot Size (Acres): 2.1
  • Zoning: 2AC
  • Lot Description: Some Wetlands, Lightly Wooded, Treed, Level Lot

Financial Considerations

  • Assessment Amount: $1,204,700
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 188517

Listed by Compass Connecticut, LLC, Pinnacle Team at Compass, Robin Halsey and Compass Connecticut, LLC, Pinnacle Team at Compass, Meg Douglas

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Listing agents

— 20 Gray Squirrel Dr —

  • Robin Halsey

    Compass Connecticut, LLC

  • Meg Douglas

    Compass Connecticut, LLC

Agent Contact: (913) 530-4367 Office Contact: (203) 423-3100

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 20 Gray Squirrel Dr

School District:New Canaan School District
NameGradesDistance
Saxe Middle School
468 South Avenue, New Canaan, CT 06840
5-81 mi
South School
8 Farm Road, New Canaan, CT 06840
K-41.1 mi
New Canaan High School
11 Farm Road, New Canaan, CT 06840
9-121.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20 Gray Squirrel Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/17/2026
Listed
$1,995,000
335.59%
MLS
5/02/1996
Sold
$458,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 20 Gray Squirrel Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$20,106
3%
$1,204,700
—
2023
$19,444
18%
$1,204,700
38%
2023
$16,526
3%
$872,550
—
2022
$16,029
1%
$872,550
—
2021
$15,846
—
$872,550
—
2020
$15,846
5%
$872,550
5%
2019
$15,093
—
$827,470
-7%
2018
$15,113
2%
$891,100
—
2017
$14,855
2%
$891,100
—
2016
$14,534
2%
$891,100
—
2015
$14,249
3%
$891,100
—
2014
$13,848
2%
$891,100
-5%
2012
$13,639
—
$934,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 20 Gray Squirrel Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Compass Connecticut, LLC, Pinnacle Team at Compass, Robin Halsey and Compass Connecticut, LLC, Pinnacle Team at Compass, Meg Douglas

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20 Gray Squirrel Drive, New Canaan, CT 06840 (MLS# 24203948) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 20 Gray Squirrel Drive is currently listed for $1,995,000 and was received on September 17, 2026. Want to learn more about 20 Gray Squirrel Drive? Do you have questions about finding other Single Family real estate for sale in New Canaan? You can browse all New Canaan real estate or contact a Coldwell Banker agent to request more information.

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