Skip main navigation
For sale
  • $649,000

    27 Tobey Hill Road, North Canaan, CT 06018

    5beds
    3,436sqft
    : 
    Single Family Residence
    Built in 1790
    3.88 Acres Lot
    $652,200 Zestimate®
    $189/sqft
    $-- HOA

    What's special

    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!
    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#: 24100923MLS Logo
    Travel times

    Tour with a buyer’s agent

    We’ll find a local expert to take you on a private tour of 27 Tobey Hill Road.

    Next available tour time:Today at 4:30pm

    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.
    • Loading
    • Loading