20 Gray Squirrel Drive
New Canaan, Connecticut 06840
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 3,530
- Acres
- 2.10
- Year Built
- 1966
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
- 0 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
Active Listings
37
20 under contract
Median List Price
$3.00M
37 active listings
Median Closed Price
$2.80M
220 sales
Median Days on Market
50
37 active listings
Median $ / Sq Ft
$676
37 active listings
Sale-to-List Ratio
101.7%
220 sales
How this home compares
List Price
$2.00M
vs $3.00M median
33.5% below median
Price / Sq Ft
$565
vs $676 median
16.4% below median
Days on Market
0 days
vs 50 days median
50 days fresher than median
Based on 37 active and 220 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of September 11, 2026.
Location
20 Gray Squirrel Drive, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$10,362
- 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
- 0
- MLS #
- 24203948
- MLS Status
- Coming Soon
Similar Properties
Homes with a close match in area, property type, and price.
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 9/11/2026. 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 9/11/2026 at 6:10 PM UTC.