40 days on market
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27 Tobey Hill Road, North Canaan CT 06018

Current Price: $649,000

5 beds 3 baths 3436 sq. ft

Last Update: 7/23/2025

Property Type: Single Family For Sale

Public Remarks

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, youll 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 homes 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!

Map to Property at 27 Tobey Hill Road, North Canaan CT 06018


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Residential Property Information for 27 Tobey Hill Road, North Canaan CT 06018

MLS #: 24100923

Style: Colonial

Color:

Total Rooms:

Bedrooms: 5

Bathrooms: 3

Acres: 3.88

Year Built: 1790 (Public Records)

New Construction: No/Resale

Home Warranty Offered:

Property Tax: $9,142

Zoning: 1

Mil Rate:

Assessed Value: $369,390 

Potential Short Sale:

Square Footage: Estimated HEATED Sq.Ft. above grade is 3436; below grade sq feet total is ; total sq ft is 3436

Features
Appliances Incl.: Microwave,Refrigerator,Dishwasher,Washer,Dryer
Laundry Location & Info: Upper Level 
Fireplaces: 4
Basement Desc.: Full,Sump Pump
Exterior Siding: Wood
Foundation: Stone
Roof: Asphalt Shingle
Parking Spaces: 1
Garage/Parking Type: Detached Garage
Swimming Pool: 0
Waterfront Feat.: Not Applicable
Lot Description: Lightly Wooded,Level Lot
Nearby Amenities: Park,Shopping/Mall
Occupied: Owner
Utility Information

Hot Water System

Heat Type:

Fueled By: Hot Water.

Cooling: Window Unit

Fuel Tank Location: In Basement

Water Service: Private Well

Sewage System: Septic

School Information

Elementary: North Canaan

Intermediate: Per Board of Ed

Middle: Per Board of Ed

High School: Housatonic

Marketing History

Current List Price: $649,000

Original List Price: $649,000

DOM: 40

Listing Date: 6/6/2025

Last Updated: 6/26/2025 10:26:11 PM

Expected Active Date: 6/12/2025

Listing Agent and Broker

List Agent Name: Tommy Connors

List Office Name: Redfin Corporation