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E. Main Street

Canaan, Connecticut 06018

ACTIVE - NEW$249,900
Beds
2
Baths
1
SqFt
1,616
Acres
0.33
Year Built
1968
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 Fireplace

About This Home

Welcome to 65 E Main Street, nestled in the quiet, close-knit town of North Canaan, in the northwest corner of Litchfield County, at the foothills of the beautiful Berkshire Mountains. This charming countryside retreat offers the perfect blend of comfort, convenience, and natural beauty. Whether you're searching for a cozy primary residence or a serene weekend getaway, this home provides a peaceful escape from the hustle and bustle of everyday life. Step outside onto your backyard deck, where you can unwind among the trees and enjoy the tranquility of nature. Outdoor enthusiasts will love the nearby hiking trails, Bunny McGuire Park, fishing along the Housatonic River, and scenic Campbell Falls. Inside, the home offers thoughtful updates and modern conveniences, including an updated kitchen and bathroom, newer appliances, modern fixtures, updated flooring, and a beautiful vaulted-ceiling dining room that adds character and an airy feel. Additional improvements include a high-efficiency heating and hot water system, propane heating, a Timberline wood stove for added warmth and charm, washer and dryer hookups, an updated concrete driveway, and new gutters. The walkout deck leads to a welcoming backyard, perfect for relaxing, entertaining, or enjoying time outdoors with family and pets. Experience the charm of countryside living without sacrificing the comforts of home. Schedule your private showing today and discover everything this special property has to off

Key Facts

City/Town
Canaan
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1968
Days on Market
0 days
Beds
2
Baths
1 full
Living Area
1,616 sq ft
Lot Size
0.33 acres
Property Taxes
$3,585 / Annually

Market Snapshot

The Canaan Market

Single Family · trailing 12 months

Median Days on Market

56

7 active listings

Median $ / Sq Ft

$400

7 active listings

Sale-to-List Ratio

95.7%

14 sales

How this home compares

List Price

$249,900

vs $1.29M median

80.7% below median

Price / Sq Ft

$155

vs $400 median

61.2% below median

Days on Market

0 days

vs 56 days median

56 days fresher than median

Based on 7 active and 14 closed sales (trailing 12 mo) of single family in Canaan. Source: SmartMLS · As of October 31, 2026.

Location

E. Main Street, Canaan, Connecticut

Property + 8 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,744

per month

  • Principal & Interest$1,362
  • Property Taxes$299
  • Insurance$83
  • HOA$0

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

Location

City/Town
Canaan
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1968
New Construction
No/Resale
Living Area
1,616 sq ft

Schools

Elementary
Lee H. Kellogg
High
Per Board of Ed

Interior

Heating
Baseboard
Heat Fuel
Propane
Cooling
None
Fireplaces
1
Laundry
Main Level
Laundry Location
laundry room located off the kithen
Appliances
Oven/RangeMicrowaveRefrigerator
Basement
Crawl Space

Exterior & Lot

Lot Size
0.33 acres
Zoning
1
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Other
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Lightly WoodedLevel LotSloping LotCleared

Listing & Financials

Property Taxes
$3,585 / Annually
Days on Market
0
MLS #
24218232
MLS Status
Active

Similar Properties

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Listed By

Alex King

(203) 533-9934

Lock and Key Realty, Inc

(413) 282-8080

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/31/2026. 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 10/31/2026 at 12:20 AM UTC.