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$630,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 1 Full Bath
  • 2 Partial Baths
  • 3,436 Sq. Ft.
  • 1 Car Garage
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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!

Full Property Details for 27 Tobey Hill Rd

General

  • Sold For: $630,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24100923
  • Added to Site: 224 day(s) ago

Interior

  • Number of Rooms: 8
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 1
  • Half Bathrooms: 2
  • Full Bath: Tub w/Shower, Laundry Hookup, Hardwood Floor, Upper
  • Partial Bath: Hardwood Floor, Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Built-Ins, Fireplace, Hardwood Floor, Main
  • Bedroom 2: Bedroom, Main
  • Bedroom 3: Bedroom - Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Fireplace, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Fireplace, Hardwood Floor, Main
  • Kitchen: Kitchen - Granite Counters, Dining Area, Fireplace, Island, Pantry, Hardwood Floor, Main
  • Dining Room: Dining Room - Built-In Hutch, Hardwood Floor, Main
  • Office: Office - Built-Ins, Fireplace, Hardwood Floor, Main
  • Laundry: Upper Level

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Parking: Detached Garage

Location

  • County: Litchfield
  • Driving Directions: Please use GPS.

School Information

  • Elementary School: North Canaan
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Housatonic

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Sump Pump
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,436
  • Above Ground: 3,436 Sq. Ft.
  • Year Built: 1790

Lot Features

  • Lot Size (Acres): 3.88
  • Zoning: 1
  • Lot Description: Lightly Wooded, Level Lot

Financial Considerations

  • Assessment Amount: $369,390
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Please see the inclusion exclusion form.
  • Property ID: 855800

Listed by Redfin Corporation, Tommy Connors
Sold by William Pitt Sotheby's Int'l, Irit Granger

Listing agent

— 27 Tobey Hill Rd —

  • Tommy Connors

    Redfin Corporation

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 27 Tobey Hill Rd

School Districts:North Canaan School District, Regional High School District 01
NameGradesDistance
North Canaan Elementary School
90 Pease Street, North Canaan, CT 06018
PK-84.4 mi
Housatonic Valley Regional High School
246 Warren Turnpike Rd., Canaan, CT 06031
9-129.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Tobey Hill Rd

Date
Details
Price
Change
Source
8/25/2025
Sold
$630,000
-2.93%
MLS
6/12/2025
Listed
$649,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Redfin Corporation, Tommy Connors
Sold by William Pitt Sotheby's Int'l, Irit Granger

27 Tobey Hill Road, North Canaan, CT 06018 (MLS# 24100923) is a Single Family property that was sold at $630,000 on August 25, 2025. Want to learn more about 27 Tobey Hill Road? Do you have questions about finding other Single Family real estate for sale in North Canaan? You can browse all North Canaan real estate or contact a Coldwell Banker agent to request more information.