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! Roof 2021, plumbing updates 2024. 2019 Well (home was previously serviced by a natural spring on the property!). Canaan has wonderful public schools and this also provides easy access to Hotchkiss, Salisbury School, Berkshire School. 20-25 minutes to Lakeville, Salisbury or Great Barrington. 15 min to Southfield store and Gedney farms. EZ access to Butternut Ski, Tanglewood and Catamount. Thousands of acres of hiking nearby at Haystack mountain, Appalachian trail or Campbells Falls. Train to NYC located in Wassaic appx 30 miles away. Cosmetic needed, but juice is well worth the squeeze, come and see for yourself!
For sale
$649,000
27 Tobey Hill Road, North Canaan, CT 06018
5beds
3,436sqft
Est.:
Single Family Residence
Built in 1790
3.88 Acres Lot
$652,200 Zestimate®
$189/sqft
$-- HOA
What's special
- 7 days
- on Zillow |
- 1,172 |
- 124 |
Zillow last checked: 7 hours ago
Listing updated: June 12, 2025 at 07:25am
Listed by:
Tommy Connors,
Redfin Corporation
Source: Smart MLS,MLS#: 24100923

Travel times
Tour with a buyer’s agent
Tour with a buyer’s agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 1
- 1/2 bathrooms: 2
Primary bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Built-in Features, Fireplace, Hardwood Floor
- Level: Main
Bedroom
- Features: Fireplace, Hardwood Floor
- Level: Upper
Bedroom
- Level: Main
Bathroom
- Features: Hardwood Floor
- Level: Main
Bathroom
- Features: Tub w/Shower, Laundry Hookup, Hardwood Floor
- Level: Upper
Dining room
- Features: Built-in Features, Hardwood Floor
- Level: Main
Family room
- Features: Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Granite Counters, Dining Area, Fireplace, Kitchen Island, Pantry, Hardwood Floor
- Level: Main
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
Office
- Features: Built-in Features, Fireplace, Hardwood Floor
- Level: Main
Heating
- Hot Water, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Upper Level
Features
- Basement: Full,Sump Pump
- Attic: Storage,Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 3,436
- Total interior livable area: 3,436 sqft
- Finished area above ground: 3,436
Video & virtual tour
Property
Parking
- Total spaces: 1
- Parking features: Detached
- Garage spaces: 1
Lot
- Size: 3.88 Acres
- Features: Few Trees, Level
Details
- Parcel number: 855800
- Zoning: 1
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1790
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Features: Park, Shopping/Mall
HOA
- Has HOA: No
Location
- Region: Canaan
Financial & listing details
- Price per square foot: $189/sqft
- Tax assessed value: $369,390
- Annual tax amount: $9,142
- Date on market: 6/6/2025
- Exclusions: Please see the inclusion exclusion form.
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