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20 Gray Squirrel Drive

New Canaan, Connecticut 06840

PENDING$1,995,000
Beds
4
Baths
2 | 1
SqFt
3,530
Acres
2.10
Year Built
1966
Matt Caiola

Matt Caiola

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2-Car Garage2 Fireplaces

About This Home

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.

Key Facts

City/Town
New Canaan
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1966
Days on Market
58 days
Beds
4
Baths
2 full · 1 half
Living Area
3,530 sq ft
Lot Size
2.10 acres
Garage / Parking
2 garage
Property Taxes
$20,440 / Annually

Market Snapshot

The New Canaan Market

Single Family · trailing 12 months

Median Days on Market

61

32 active listings

Median $ / Sq Ft

$677

32 active listings

Sale-to-List Ratio

102.4%

210 sales

How this home compares

List Price

$2.00M

vs $3.85M median

48.1% below median

Price / Sq Ft

$565

vs $677 median

16.5% below median

Days on Market

58 days

vs 61 days median

In line with median

Based on 32 active and 210 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of November 8, 2026.

Location

20 Gray Squirrel Drive, New Canaan, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$13,180

per month

  • Principal & Interest$10,812
  • Property Taxes$1,703
  • Insurance$665
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
New Canaan
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1966
New Construction
No/Resale
Living Area
3,530 sq ft
Below Grade
318 sq ft

Schools

Elementary
South
High
New Canaan

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
2
Laundry
Main Level
Appliances
Gas CooktopWall OvenMicrowaveSubzeroDishwasherWasherDryer
Basement
FullSump PumpStorageGarage AccessInterior AccessPartially Finished
Additional Rooms
Bonus RoomExercise RoomLaundry RoomMud RoomWorkshop

Exterior & Lot

Lot Size
2.10 acres
Zoning
2AC
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
ShingleWood
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BarnDeck
Lot Description
Some WetlandsLightly WoodedTreedLevel Lot

Listing & Financials

Property Taxes
$20,440 / Annually
Days on Market
58
MLS #
24203948
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Robin Halsey

(913) 530-4367

Compass Connecticut, LLC

(203) 423-3100

Co-Listed By

Meg Douglas

Compass Connecticut, LLC

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/8/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 11/8/2026 at 8:50 AM UTC.