The Matthews GroupWilliam Raveis

The Matthews Group

North Canaan CT Real Estate

North Canaan is in the northwest corner of the state at the junctions of Route 44 and Route 7. The Canaan Railroad Station is the oldest railroad station in continuous service in the country. Children in grades K-8 attend K-8 North Canaan Elementary School. Browse all real estate and homes for sale in North Canaan, CT below. 

North Canaan Real Estate

Contact The Matthews Group at 860-868-0511 with any questions or to schedule a private tour.

Time Saving Tip: Sign up for a free account to save your favorite listings and get notified when new properties match your criteria.

39 Carlson Road North Canaan CT 06018
Open House

MLS Number 170439167

  • Single Family
  • Next Open House: Sun 10/17 1:00 pm. to 3:00 pm.
  • Square Feet 3,152
  • Bathroom 3
  • Property Style Contemporary

Two homes are nestled on this 6.6 acre parcel in Canaan Valley - a custom contemporary home built in 1990 with acccess from Carlson Road and a smaller tenant house built in 1880 with access from Moses Meade Road. The property also includes a 30x30 horse barn with 3 horse stalls and one pony stall and another large barn that could be repurposed as a large studio or workspace. Open land provides space for horse pasture. The custom contemporary has large spacious rooms, including a master bedroom ensuite on the first floor that includes 5 closets, full bath and dressing room. Large eat in kitchen with decorative antique Glendale Cookstove. Formal dining room could also serve as a 2nd bedroom on the first floor. Large living room with fireplace. Den with built-ins and fireplace leads out to large, bright sun room that overlooks the field. The first floor also includes a laundry room, pantry and half bath. The second floor includes a large L-shaped loft with Palladian windows, bedroom and full bath. Walk into a large attic space that could also potentially serve as another bedroom or family room. Two car attached garage with large space above can be finished for a home office. 14x9 screened porch on back of home. Propane furnace is two years old. Auto-Generator. The 1,267 sq. ft. tenant house is a two bedroom, two bathroom home that is currently rented. All room sizes are approximate.

Listing Courtesy of Raynard & Peirce Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

176 Lower Road North Canaan CT 06024
Open House

MLS Number 170441326

  • Single Family
  • Next Open House: Sat 10/16 10:00 am. to 12:00 pm.
  • Square Feet 2,088
  • Bathroom 2
  • Property Style Colonial

Enjoy beautiful view of Canaan Mountain from this renovated circa 1825 home with new 56x56 insulated workshop. This 5 bedroom home sits on two nicely landscaped acres. Many newer upgrades include septic, roof, furnace, decking, water tank, appliances and front porch. First floor bedroom can also serve as office. A full bathroom on each floor - upstairs bathroom includes laundry hookups. Original wide board chestnut flooring. Pellet Stove in Living Room. Additional wood stove in basement. 23x22 deck facing the mountains. The large workshop was built in 2016. This is perfect for work and play! Large area upstairs can be finished for game room/office or potential living space. Workshop is well insulated and prepped for radiant heat All room sizes are approximate.

Listing Courtesy of Raynard & Peirce Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

180 West Main Street North Canaan CT 06018
Pending Continue to Show

MLS Number 170438332

  • Multi Family Multi-Family For Sale
  • Square Feet 4,788
  • Bathroom 6
  • Year Built 1910
  • Bedrooms 10

This seven unit apartment building is an income generating machine... Units are well maintained with separate utilities for each apartment. Grounds are clean, with ample parking and private entrances to each unit. Propane heat systems are all separately metered. Town water and sewer. The apartments are fully occupied due to the location, on a convenient side street well within walking distance to town. Newer roof and a nicely done recent exterior paint job compliment this building's grand appearance. One of the owners is a licensed real estate agent.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

12 Church Terrace North Canaan CT 06018

North Canaan, CT12 Church Terrace

Price$498,000

Est. Mortgage: $/month

MLS Number 170428663

  • Single Family
  • Square Feet 2,637
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1818

Affordability with lots of space and an in-ground pool in the Litchfield Hills! This move-in ready home offers generous rooms with well-maintained conditions both inside and out. Add newer replacement windows, abundant foam insulation, & a newer boiler & HWH to what you can see in the photos, and you have a complete package. The current owner has maintained historic period features and incorporated pleasant contemporary finishes inside, and the outside offers a recently-built, spacious 3 car garage, a 7-run dog kennel easily converted to a workshop or office, and a beautiful pool in a private setting. This home has been cared for, details have received love and attention, and this critically important fact shows throughout. Town water and sewer too! Close proximity to town, close proximity to nature, hiking trails, and recreation, and close proximity to all the wonderful entertainment and events that the Litchfield Hills and the Berkshires have to offer. This is a great opportunity; don't let it pass by...

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

76 South Canaan Road North Canaan CT 06018

MLS Number 170442286

  • Single Family
  • Square Feet 3,708
  • Property Style Colonial
  • Bathroom 2
  • Year Built 1762

Built in 1762 and one of the first few homes to be built in North Canaan. This home is a total renovation project with great potential! Large home located next to a golf course also has commercial income with rental buildings. Large 2,880 sq ft. workshop is currently rented along with 5 attached garages that also provide income. Large two room former office is also attached to this house. Post and Beam house with original wide board flooring. Large rooms, 4 fireplaces. 4 bedrooms upstairs. Property contains 17+ acres - approximately four acres surround house and buildings and an additional 13 acre bird & wildlife sanctuary. This home will be spectacular once restored to it's original state. All room sizes are approximate.

Listing Courtesy of Raynard & Peirce Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

278 Ashley Falls Road North Canaan CT 06018

MLS Number 170440852

  • Single Family
  • Square Feet 3,058
  • Property Style Colonial
  • Bedrooms 5
  • Year Built 1805

This spacious and gracious 1805 colonial is set privately on top of a hill and surrounded by trees. A great weekend getaway, or a full time home only 5 mins away from the Berkshires. This gorgeous home has an abundance of bedrooms and bathrooms, unlike many older homes, there are many walk-in closets. Wide-board hardwood floors throughout and new double-paned windows help plant your feet and keep out the cold. The primary suite features a fireplace, full bathroom, and private staircase. It also easily connects to the rest of the bedrooms through two different doors. The living room has two glass-paned doors that open up onto a patio for a relaxing experience, and during the colder months, the living room also has an original wood-burning stove equipped with an 1800's cooking pot. The flow between the oversized dining room with fireplace, living room, and eat-in kitchen offers great opportunities for entertaining. The main level includes a half bath and office. On the second floor, youll find a full bath, three bedrooms, one of which has a private screened-in porch. There is an oversized post and beam 2 car garage, that could easily be made into a workshop with the preexisting underground electricity and plumbing. Conveniently located at the intersection of Ashley Falls rd (Rte 7) and N Elm Street. The 1.96 acres property can easily be subdivided along Rte 7 and Ashley Falls rd, or additional buildings could be added.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

110 Granite Avenue North Canaan CT 06018

North Canaan, CT110 Granite Avenue

Price$420,000

Est. Mortgage: $/month

MLS Number 170437881

  • Single Family
  • Square Feet 2,219
  • Year Built 1860
  • Property Style Colonial
  • Bathroom 2

CLASSIC VILLAGE DUTCH COLONIAL - Well loved by the same family for 78 years, this home pairs the best of vintage quality construction with modern updates and amenities, attractively set on a level 0.75 acre lot. Fir and maple flooring, bright window seats in many rooms, built in bookcases, high ceilings, bay windows, a wonderful covered Front Porch, all combining in a gracious, comfortable home. This desirable neighborhood, in close proximity to everything in town, is a place to call home. Pharmacy, post office, library, groceries, a playground, a lifeguarded town pool, restaurants, a brewery - all close by. You are centrally located for all that the Litchfield Hills and Southern Berkshires have to offer. Hiking, biking, world-class fishing, skiing, Yale Summer Music in Norfolk, Tanglewood - this is just the beginning of the list - and a ride to Wassaic train station brings ample parking and a comfortable trip for a visit to NYC. Come see for yourself!

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

340 West Main Street North Canaan CT 06018

MLS Number 170421944

  • Single Family
  • Square Feet 1,656
  • Bedrooms 4
  • Bathroom 1
  • Year Built 1890

Canaan 8 room 4 bedroom colonial situated on 1.75 acres set back from the road, with vinyl siding, all new thermopane windows, one car garage, walk up attic, and full basement, within walking distance to town and shopping.

Listing Courtesy of Giumarro Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

43 Greene Avenue North Canaan CT 06018

MLS Number 170440752

  • Single Family
  • Square Feet 2,106
  • Property Style Saltbox
  • Bedrooms 2
  • Bathroom 3

Green Acres Community is North Canaan's best kept secret! The quiet neighborhood lined with beautiful trees and forestry is conveniently located to public and private schools, main street shopping, and all of the entertainment that Great Barrington, MA has to offer. This 1987 Saltbox has been recently updated with new kitchen appliances and bathroom vanities and fixtures. The home has been freshly painted and new light fixtures have been installed throughout. The walk out basement has a half bath and laundry room and provides another space with endless opportunities for a rec room or family room. The wrap around deck provides the perfect relaxation for peaceful living or plenty of space for entertaining. Nearby amenities include Twin Lakes and O'Hara's Marina; Catamount Ski Area and Ski Butternut, and plenty of hiking along the Appalachian trail.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

425 Ashley Falls Road North Canaan CT 06018

MLS Number 170420938

  • Single Family
  • Square Feet 2,112
  • Bathroom 3
  • Bedrooms 4
  • Property Style Colonial

Stately 5 bedroom home owned by same family for 50+ years. Occupied by 2 generations. 1940 Colonial w/country kitchen, LR w/fireplace, master bed w/full bath on first floor, sun room off LR w/ 1/2 bath. Upstairs 4 bedrooms w/ full bath. Full walk up attic. Grounds include 20 X 40 inground swimming pool, Large detached 2 car garage w/ ample storage, shed, a beautiful, private, flat lot in backyard. Many happy memories await the next family &/Or tradesman for commercially zoned use. Public Sewer & Water. Newer updates include windows, roof, furnace. Close proximity to town, amenities, & MA border.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

62 Granite Avenue North Canaan CT 06018

North Canaan, CT62 Granite Avenue

Price$375,000

Est. Mortgage: $/month

MLS Number 170438562

  • Multi Family Multi-Family For Sale
  • Square Feet 3,004
  • Year Built 1889
  • Bathroom 3
  • Bedrooms 7

This three apartment multi-family has a steady income stream. The building and grounds are well maintained with a small garage/shed as possible storage. Each apartment has separate utilities. There's a spacious yard with ample parking and each apartment has a private entrance. Heat is provided by a propane fired hot air system for the 1st floor unit, a propane fired hot water baseboard system for the 2nd floor unit, and zoned electric baseboard system for the 3rd floor unit. Town water and sewer. The apartments are fully occupied due to the location, on a convenient side street well within walking distance to town. One of the owners is a licensed real estate agent.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

172 Clayton Road North Canaan CT 06018

MLS Number 170427954

  • Single Family
  • Square Feet 1,832
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1988

Come make this house your next home! It has never been on the market before. It's been cared for and thoughtfully updated over the years by the meticulous owner. It offers single level living at it's finest. The functional layout makes for easy entertaining. All of the bedrooms are located on one side of the home and the living room, dinning room, covered deck, and kitchen are on the other. There is a full bath located between the living and sleeping quarters, so guest have easy access. The main bedroom is ensuite and spacious. The basement has a partially finished area and a work shop, but could easily be converted to expand the square footage of the home. The oversized 2 car garages offers an abundance of storage space for all of your gear. There are hikes, breweries, and eateries in abundance. Only 18 minutes from Great Barrington and 37 minutes to Tanglewood.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.