287 West Main Street
North Canaan, Connecticut 06018
Reduced from $369,000
- Beds
- 3
- Baths
- 1
- SqFt
- 1,784
- Acres
- 0.52
- Year Built
- 1929
- Neighborhood
- Canaan Village
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
- 84 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
- $4,458 / Annually
Market Snapshot
The North Canaan Market
Single Family · trailing 12 months
Active Listings
9
4 under contract
Median List Price
$535,000
9 active listings
Median Closed Price
$365,000
29 sales
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
$359,000
vs $535,000 median
32.9% below median
Price / Sq Ft
$201
vs $227 median
11.5% below median
Days on Market
84 days
vs 62 days median
22 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
287 West Main Street, North Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,830
- Property Taxes$372
- Insurance$120
- 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
- $4,458 / Annually
- Days on Market
- 84
- MLS #
- 24172528
- MLS Status
- Active
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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 6:10 AM UTC.