27 Tobey Hill
North Canaan, CT 06018
Map
- 5 beds
- 3 baths
- 3,436 sqft
- ~4 acre lot
- $188 per sqft
- 1790 build
- – on site
Nestled in the foothills of the Berkshires on a quiet country road, this circa 1790 colonial, "The Tobey House," awaits its new stewards! This special property features authentic period details & is sited on a majestic 3.88 acre lot with direct access to the waterfalls at Campbells Falls. The sprawling, versatile floorplan is the perfect canvas to bring your antique Pinterest board to life! With windows in all the right places, the home is awash in natural light that perfectly showcases the rich patina of the wide plank flooring and rustic detailing throughout. Entering the architect-designed kitchen, you'll take a deep breath: this is truly a HOME. Cabinet packed with a large granite island overlooking one of 7 (4 functional) original fireplaces, it creates the perfect command center. Built-in enthusiasts will marvel at the absolutely stunning carpentry in every room. An XL dining room flows seamlessly into a charming den. The lovely center hall provides access to the ultimate work from home wing, guest room with ensuite 1/2 bath, & a fantastic covered porch overlooking the pastoral grounds, former pool area w hookups still intact, & massive barn. Upstairs, the capacious primary BR is adorned with hand-stenciled walls. 2 addl well sized BRs share a massive full bath w laundry. Ideal location on MA line - the perfect launch point to enjoy the best of the Berkshires & NW corner. This home's rich heritage is ready to converge with your next chapter: a dream homestead beckons!
Last checked:
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Last updated Jun 12, 2025
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MLS# 24100923 —
The Building
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Year Built:1790
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Year Built Source:Public Records
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New Construction Type:No/Resale
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Style:Colonial
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Roof Information:Asphalt Shingle
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Attic:Yes
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Attic Description:Storage Space, Walk-up
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Exterior Siding:Wood
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Foundation Type:Stone
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Basement Description:Full, Sump Pump
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SqFt Total:3436
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SqFt Est Heated Above Grade:3436
Interior
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Fireplaces Total:4
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Laundry Room:Upper Level
Room Dimensions
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Living Area SqFt Per Public Record:3436
Location
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Directions:Please use GPS.
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Neighborhood:N/A
The Property
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Parcel Number:855800
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Property Type:Single Family For Sale
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Zoning:1
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Acres:3.88
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Acres Source:Public Records
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Lot Description:Lightly Wooded, Level Lot
Listing Agent
- Contact info:
- Agent phone:
- (203) 349-8711
Taxes
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Tax Year:July 2024-June 2025
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Property Taxes:9142
Beds
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Beds Total:5
Baths
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Total Baths:3
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Full Baths:1
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Half Baths:2
The Listing
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https://my.matterport.com/show/?m=oeawQ93Gj3K
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Home Warranty Offered:No
Heating & Cooling
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Heat Type:Hot Water
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Heat Fuel Type:Oil
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Cooling System:Window Unit
Utilities
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Water Source:Private Well
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Sewage System:Septic
Appliances
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Appliances Included:Microwave, Refrigerator, Dishwasher, Washer, Dryer
Schools
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Elementary School:North Canaan
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Intermediate School:Per Board of Ed
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Middle Or Junior School:Per Board of Ed
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High School:Housatonic
The Community
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Nearby Amenities:Park, Shopping/Mall
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Swimming Pool:No
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Direct Waterfront:No
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Waterfront Description:Not Applicable
Parking
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Garage & Parking:Detached Garage
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Garages Number:1
Monthly cost estimate
Asking price
$649,000
| Expense | Monthly cost |
|---|---|
|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$3,475
|
| Taxes | N/A |
| Insurance | $178 |
| Utilities | $502 See report |
| Total | $4,155/mo.* |
| *This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
| Date | Event | Source | Price | % Change |
|---|---|---|---|---|
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6/11/25
Jun 11, 2025
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Listed / Active | SMART_MLS | $649,000 | |
|
6/6/25
Jun 6, 2025
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Coming Soon | SMART_MLS | $649,000 |
