27 Tobey Hill Road, North Canaan, Connecticut

$649,000

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5

Beds

3

Baths

3,436

Square feet

3.88

Acres

About 27 Tobey Hill Road

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!

Features of 27 Tobey Hill Road

MLS® # 24100923
Price $649,000
Bedrooms 5
Bathrooms 3.00
Full Baths 1
Half Baths 2
Square Footage 3,436
Acres 3.88
Type Single Family For Sale
Style Colonial
Status Under Contract - Continue to Show

Community Information

Address 27 Tobey Hill Road
Area N/A
City North Canaan
County Litchfield
State Connecticut
Zip Code 06018

Amenities

Parking Detached Garage
# of Garages 1
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Microwave, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Water, Oil
Cooling Window Unit
Fireplace Yes
# of Fireplaces 4
Has Basement Yes
Basement Full, Sump Pump

Exterior

Exterior Wood
Lot Description Lightly Wooded, Level Lot
Roof Asphalt Shingle
Foundation Stone

School Information

Elementary North Canaan
Middle Per Board of Ed
High Housatonic

Additional Information

Date Listed June 6th, 2025
Days on Market 26
Zoning 1
RE / Bank Owned No

Listing Details

OfficeRedfin Corporation

Listing Map

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Listing information last updated on July 8th, 2025 at 6:45am EDT.