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287 West Main Street

North Canaan, Connecticut 06018

ACTIVE$320,000

Reduced from $369,000

Beds
3
Baths
1
SqFt
1,784
Acres
0.52
Year Built
1929
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 FireplacePrice Reduced

About This Home

Nestled on a level in-town lot, this classic Colonial offers timeless charm, solid construction, and endless potential. Featuring three bedrooms and beautiful hardwood flooring, the home provides a warm and inviting layout ready for your personal touch. The front porch is THE perfect seasonal place to unwind after a long day or start your day with coffee! The adorable galley kitchen with convenient main-level laundry adds to the home's functionality, while a detached two-car garage offers additional storage and versatility. While the property could benefit from some cosmetic updates, it has been well maintained and stands on a strong foundation-making it the perfect opportunity to build equity and create your dream home. Located in the heart of Canaan, you'll enjoy the best of small-town living with the convenience of being able to walk right into town. Known for its scenic beauty and rich history, this charming Litchfield Hills community is home to the stunning Great Falls and the unique New England Accordion Connection & Museum Company. Surrounded by nature, outdoor recreation, local dining, and a peaceful rural atmosphere, Canaan offers a lifestyle that's hard to leave once you experience it. Whether you're looking for your first home, a weekend retreat, or a place to put down roots, this property is a rare opportunity to become part of a truly special community.

Key Facts

City/Town
North Canaan
Neighborhood
Canaan Village
Property / Style
Single Family · Colonial
Year Built
1929
Days on Market
178 days
Beds
3
Baths
1 full
Living Area
1,784 sq ft
Lot Size
0.52 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$4,094 / Annually

Market Snapshot

The North Canaan Market

Single Family · trailing 12 months

Median Days on Market

116

10 active listings

Median $ / Sq Ft

$243

10 active listings

Sale-to-List Ratio

98.0%

25 sales

How this home compares

List Price

$320,000

vs $479,450 median

33.3% below median

Price / Sq Ft

$179

vs $243 median

26.3% below median

Days on Market

178 days

vs 116 days median

62 days longer than median

Based on 10 active and 25 closed sales (trailing 12 mo) of single family in North Canaan. Source: SmartMLS · As of October 30, 2026.

Location

287 West Main Street, North Canaan, Connecticut

Property + 6 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,193

per month

  • Principal & Interest$1,745
  • Property Taxes$341
  • Insurance$107
  • HOA$0

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

Location

City/Town
North Canaan
Neighborhood
Canaan Village
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1929
New Construction
No/Resale
Living Area
1,784 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Steam
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Laundry
Main Level
Appliances
None
Basement
FullFull With Hatchway
In-Law Apartment
No

Exterior & Lot

Lot Size
0.52 acres
Zoning
2
Garage / Parking
2 garage spaces6 total parking spacesDetached GarageOff Street Parking
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
MasonryStone
Exterior Features
Garden Area
Lot Description
Level Lot

Listing & Financials

Property Taxes
$4,094 / Annually
Days on Market
178
MLS #
24172528
MLS Status
Active

Similar Properties

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Listed By

Suzie Larson

(860) 601-3730

Turning Point Realty, LLC

(860) 909-1162

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/30/2026. 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 10/30/2026 at 6:45 PM UTC.