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Sold for $630,000
  • $630,000

    27 Tobey Hill Road, North Canaan, CT 06018

    5beds
    3,436sqft
    Single Family Residence
    Built in 1790
    3.88 Acres Lot
    $632,900 Zestimate®
    $183/sqft
    $4,552 Estimated rent

    Home value

    $632,900

    $601,000 - $665,000

    $4,552/mo

    Zestimate® history
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    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!

    Zillow last checked: 8 hours ago

    Listing updated: January 26, 2026 at 08:46am

    Listed by:

    Tommy Connors 978-809-0965,

    Redfin Corporation 203-349-8711

    Bought with:

    Irit R. Granger, REB.0759006

    William Pitt Sotheby's Int'l

    Source: Smart MLS,MLS#: 24100923MLS Logo

    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: Built-in Features, Fireplace, Hardwood Floor
    • Level: Main
    Bedroom
    • Features: Fireplace, Hardwood Floor
    • Level: Upper
    Bedroom
    • Features: 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

    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 & neighborhood

    Community
    • Community features: Park, Shopping/Mall
    Location
    • Region: Canaan

    Price history

    DateEventPrice
    8/25/2025Sold$630,000-2.9%$183/sqft
    Source: Smart MLS #24100923 Report a problem
    6/12/2025Listed for sale$649,000$189/sqft
    Source: Smart MLS #24100923 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$9,142 $369,390
    2024$9,142 -2.9%$369,390
    2023$9,419 +9.1%$369,390 +32.7%

    Find assessor info on the county website

    Neighborhood: North Canaan

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: North Canaan
    • High: Housatonic

    Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    $632,900
    2% more+$12,658
    With Zillow Showcase(estimated)$645,558