27 Tobey Hill Road, North Canaan, CT 06018
Local realty services provided by:ERA Treanor Real Estate



27 Tobey Hill Road,North Canaan, CT 06018
$649,000
- 5 Beds
- 3 Baths
- 3,436 sq. ft.
- Single family
- Pending
Listed by:tommy connors
Office:redfin corporation
MLS#:24100923
Source:CT
Price summary
- Price:$649,000
- Price per sq. ft.:$188.88
About this home
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!
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Home facts
- Year built:1790
- Listing Id #:24100923
- Added:69 day(s) ago
- Updated:August 14, 2025 at 10:42 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:3
- Full bathrooms:1
- Half bathrooms:2
- Living area:3,436 sq. ft.
Heating and cooling
- Cooling:Window Unit
- Heating:Hot Water
Structure and exterior
- Roof:Asphalt Shingle
- Year built:1790
- Building area:3,436 sq. ft.
- Lot area:3.88 Acres
Schools
- High school:Housatonic
- Middle school:Per Board of Ed
- Elementary school:North Canaan
Utilities
- Water:Private Well
Finances and disclosures
- Price:$649,000
- Price per sq. ft.:$188.88
- Tax amount:$9,142 (July 2025-June 2026)
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