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277 Ashley Falls Road

North Canaan, Connecticut 06018

ACTIVE$349,900

Reduced from $399,000

Beds
2
Baths
2
SqFt
2,127
Acres
1.47
Year Built
2001
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

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1 FireplacePrice Reduced

About This Home

A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef , a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the house is in pristine shape for the next owner. Finally, there is central air on the second floor to complete the full package!

Key Facts

City/Town
North Canaan
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
2001
Days on Market
1037 days
Beds
2
Baths
2 full
Living Area
2,127 sq ft
Lot Size
1.47 acres
Garage / Parking
10 total
Property Taxes
$6,580 / Annually

Market Snapshot

The North Canaan Market

Single Family · trailing 12 months

Median Days on Market

62

9 active listings

Median $ / Sq Ft

$227

9 active listings

Sale-to-List Ratio

97.4%

29 sales

How this home compares

List Price

$349,900

vs $535,000 median

34.6% below median

Price / Sq Ft

$165

vs $227 median

27.3% below median

Days on Market

1037 days

vs 62 days median

975 days longer than median

Based on 9 active and 29 closed sales (trailing 12 mo) of single family in North Canaan. Source: SmartMLS · As of July 28, 2026.

Location

277 Ashley Falls Road, North Canaan, Connecticut

Property + 6 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,449

per month

  • Principal & Interest$1,784
  • Property Taxes$548
  • Insurance$117
  • HOA$0

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

Location

City/Town
North Canaan
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
2001
New Construction
No/Resale
Living Area
2,127 sq ft

Schools

Elementary
NCES
High
Housatonic

Interior

Heating
Baseboard
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Appliances
Cook TopRefrigerator
Basement
Crawl Space
Accessibility
Ramps

Exterior & Lot

Lot Size
1.47 acres
Zoning
4
Garage / Parking
10 total parking spacesOff Street ParkingPrivate
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Block
Lot Description
Open LotSome Wetlands

HOA / Association

Amenities
None

Listing & Financials

Property Taxes
$6,580 / Annually
Days on Market
1037
MLS #
170599770
MLS Status
Active

Similar Properties

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

Listed By

John Harney

(860) 921-7910

William Pitt Sotheby's Int'l

(860) 435-2400

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 7:45 AM UTC.