North Canaan, CT Homes

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  $345,000

  • Land
  • 37.44 Acres
  • $9,215 per Acre

  0 Old Turnpike Rd N, Canaan, CT 06018

  37.437 acres bordering the Konkapot River. A small portion of this land on the back side is in Massachusetts. New survey is complete. Nice location with great possibilities!

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 609-6471

  0 Old Turnpike Rd N, Canaan, CT 06018
• Explore North Canaan

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  /7

  $1,875 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  29 E Main St Unit B3, Canaan, CT 06018

  Welcome to this beautifully designed brand-new rental offering modern comfort, thoughtful design, and an unbeatable location. This newly constructed apartment showcases an outstanding use of space, that is both stylish and functional. The primary suite is a true highlight, featuring a spacious layout with a large walk-in closet and a private ensuite bathroom, providing the perfect retreat at the

  

  Annie Q Simard

  LPT Realty

  (860) 609-6279

  29 E Main St Unit B3, Canaan, CT 06018
• 

  $654,000 Sold Dec 05, 2025

  19 Ryan Ave, Canaan, CT 06018

  • 2 Beds
  • 2.5 Baths
  • 2,299 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $284/SF
  • 83 Days On Market

  Current Estimated Value $667,772

  Last Listing Agent Phil Fox William Pitt Sotheby's Int'l

  19 Ryan Ave, Canaan, CT 06018
• 

  Est $308,323 Not Listed For Sale

  10 Railroad St, Canaan, CT 06018

  • 2 Beds
  • 1.5 Baths
  • 1,900 Sq Ft
  • Built 1845

  10 Railroad St, Canaan, CT 06018

  Last Sold Summary

  • 5% Above List Price
  • $155/SF
  • 97 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Liza Reiss Elyse Harney Real Estate
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  /33

  $369,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  37 Greene Ave, Canaan, CT 06018

  Welcome home to this beautifully maintained 1,332 sq ft, 7-room gem nestled in the charming town of North Canaan. Set on a lightly wooded half-acre lot, this sun-filled home offers the perfect blend of comfort, style, and space. Step inside to find neutral tones and elegant decor that create a warm, inviting atmosphere throughout. In addition to three comfortable bedrooms and one full updated

  Jennifer Albanesi Berkshire Hathaway NE Prop.

  37 Greene Ave, Canaan, CT 06018
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  /4

  $1,350 plus fees

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  31-33 Railroad St Unit 5, Canaan, CT 06018

  Property Id: 2466755Nicely updated 1-bedroom apartment is. On-site laundry facilities, pet-friendly, and move-in ready.Rental Requirements:- Credit score of at least 650- Monthly income must be 3x the rent- No history of evictions- Security deposit of 1 months' rent and 1st month's rent required to move in- Minimum 1-year lease required

  31-33 Railroad St Unit 5, Canaan, CT 06018
• 

  $279,900 Sold Jun 02, 2025

  88 Lower Rd, Canaan, CT 06018

  • 3 Beds
  • 2 Baths
  • 2,212 Sq Ft
  • Built 1965

  Last Sold Summary

  • 7% Below List Price
  • $127/SF
  • 18 Days On Market

  Current Estimated Value $313,814

  Last Listing Agent Sean Doran Social & Co Realty

  88 Lower Rd, Canaan, CT 06018
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  Est $297,801 Not Listed For Sale

  140 W Main St, Canaan, CT 06018

  • 3 Beds
  • 2 Baths
  • 1,378 Sq Ft
  • Built 1920

  140 W Main St, Canaan, CT 06018

  Last Sold Summary

  • 1% Below List Price
  • $218/SF
  • 66 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Linda Ganem Borla & Associates Real Estate
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  $1,235,000

  • 3 Beds
  • 3 Baths
  • 2,460 Sq Ft

  35 Emmons Ln, Canaan, CT 06018

  CANAAN VALLEY LUXURY - FULLY FURNISHED - TURNKEY LIVING - The total renovation of this beautifully located single level home, rebuilt from the foundation up in 2024, has been done with unparalleled taste and style. Set just above the Whiting River and overlooking preserved land in an area of estate level properties, the serenity and timeless appeal of Canaan Valley surround you. The result is a

  David Taylor Elyse Harney Real Estate

  35 Emmons Ln, Canaan, CT 06018
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  /19

  $3,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,036 Sq Ft
  • House for Rent

  14 Browns Ln, East Canaan, CT 06024

  Experience modern luxury meets serene country living in this meticulously custom-renovated 3-bedroom, 2.5-bath home. Thoughtfully redesigned with premium finishes throughout, this residence offers the ultimate in comfort and contemporary style for discerning tenants. Enter through the welcoming foyer into a chef's delight of a kitchen-open, bright, and perfectly appointed for both everyday living

  David Hurlburt William Pitt Sotheby's Int'l

  14 Browns Ln, East Canaan, CT 06024
• 

  $1,115,000 Sold Sep 10, 2025

  36 Old Turnpike Rd N, Canaan, CT 06018

  • 3 Beds
  • 4 Baths
  • 3,472 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 54 Days On Market

  Last Listing Agent Elyse Morris Elyse Harney Real Estate

  36 Old Turnpike Rd N, Canaan, CT 06018
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  Est $642,512 Not Listed For Sale

  5 Elm St, Canaan, CT 06018

  • 7 Beds
  • 2.5 Baths
  • 4,852 Sq Ft
  • Built 1810

  5 Elm St, Canaan, CT 06018

  Last Sold Summary

  • 31% Above List Price
  • $101/SF
  • 293 Days On Market

  Last Sold Price $489,900

  Last Listing Agent Juliet Moore Elyse Harney Real Estate
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  /17

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  10 College Hill Rd, Canaan, CT 06018

  Privacy and Winter Views - This is a sweet Cape at the end of a private road. Features include a large Great Room with Living Room, Dining Area, and Kitchen, plus Mudroom with half Bath. The Primary Bedroom is on the Main Floor with Full Bath and walk-in closet, and 2 additional Bedrooms and a Full Bath are on the Second Floor. A large finished Family Room on the Lower Level with a Full Bath /

  Juliet Moore Elyse Harney Real Estate

  10 College Hill Rd, Canaan, CT 06018
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  $2,350 per month

  • 3 Beds
  • 1.5 Baths
  • 1,470 Sq Ft
  • House for Rent

  15 Lower Rd, Canaan, CT 06018

  $2,350 per month - utilities not included. Available starting Monday, March 22. This is a private, furnished single-family home featuring three bedrooms and one and a half bathrooms, located just steps from the Blackberry River. A private staircase behind the house provides direct access to the riverbank, offering a unique outdoor setting. The home includes a kitchen, dining area, living room,

  Jorge Zea Blue Lighthouse Realty, Inc

  15 Lower Rd, Canaan, CT 06018
• 

  $412,500 Sold Sep 10, 2025

  43 Greene Ave, Canaan, CT 06018

  • 2 Beds
  • 3 Baths
  • 2,246 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $184/SF
  • 123 Days On Market

  Current Estimated Value $425,408

  Last Listing Agent David Hurlburt William Pitt Sotheby's Int'l

  43 Greene Ave, Canaan, CT 06018
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  Est $362,513 Not Listed For Sale

  72 Old Turnpike Rd, Canaan, CT 06018

  • 3 Beds
  • 2 Baths
  • 1,659 Sq Ft
  • Built 1950

  72 Old Turnpike Rd, Canaan, CT 06018

  Last Sold Summary

  • 1% Below List Price
  • $220/SF
  • 39 Days On Market

  Last Sold Price $365,000

  Last Listing Agent David Sartirana Northwest CT Realty
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  /24

  $198,500

  • 2 Beds
  • 1.5 Baths
  • 890 Sq Ft

  70 Church St Unit D1, Canaan, CT 06018

  Skip the renovations and move straight into this chic, end-unit townhouse where "new" is the recurring theme. Every inch of this 2BR condo has been curated for modern tastes, featuring all-new flooring, sleek cabinetry, and stone counters. The open, light-filled layout is complemented by a fresh designer palette and brand-new stainless appliances. The dry basement level with high ceilings is

  David Mallison William Pitt Sotheby's Int'l

  70 Church St Unit D1, Canaan, CT 06018
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  $365,000 Sold Aug 08, 2025

  101I Sand Rd, Canaan, CT 06018

  • 3 Beds
  • 2 Baths
  • 1,733 Sq Ft
  • Built 1986

  Last Sold Summary

  • $211/SF
  • 42 Days On Market

  Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC

  101I Sand Rd, Canaan, CT 06018
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  Est $291,512 Not Listed For Sale

  275 W Main St, Canaan, CT 06018

  • 6 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 1900

  275 W Main St, Canaan, CT 06018

  Last Sold Summary

  • 8% Above List Price
  • $126/SF
  • 56 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC
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  /13

  $220,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  41 Prospect St, Canaan, CT 06018

  Looking for small town charm, a country home, investment property or weekend retreat? This one level, three bedroom, two bath home is waiting for your creative vision. Situated on a quiet street, filled with natural light, hardwood flooring, enclosed front porch and detached garage. Just minutes to local shops, short drive to the Berkshires and a great location for outdoor enthusiasts. This home

  Dawn Sanderson Northwest CT Realty

  41 Prospect St, Canaan, CT 06018
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  $310,000 Sold Dec 05, 2025

  101-7 Sand Rd, Canaan, CT 06018

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1987

  Last Sold Summary

  • $196/SF
  • 48 Days On Market

  Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC

  101-7 Sand Rd, Canaan, CT 06018
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  Est $258,798 Not Listed For Sale

  9 Lawrence Ave, Canaan, CT 06018

  • 2 Beds
  • 1.5 Baths
  • 1,109 Sq Ft
  • Built 1937

  9 Lawrence Ave, Canaan, CT 06018

  Last Sold Summary

  • 18% Above List Price
  • $198/SF
  • 12 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC
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  /37

  $1,095,000 Under Contract

  • 6 Beds
  • 2.5 Baths
  • 4,753 Sq Ft

  143 E Canaan Rd, East Canaan, CT 06024

  Exceptional country estate on 16.65 pristine acres offering the ultimate in privacy and convenience without isolation. This remarkable North Canaan property features a 3 car garage-ideal for automotive enthusiasts to enjoy nearby Lime Rock Park. Inside, the chef's kitchen with commercial prep area is an entertainer's paradise, designed to accommodate everything from intimate dinners to

  Phil Fox William Pitt Sotheby's Int'l

  143 E Canaan Rd, East Canaan, CT 06024
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  $297,000 Sold Aug 20, 2025

  7 Lawrence Ave, Canaan, CT 06018

  • 3 Beds
  • 3 Baths
  • 1,456 Sq Ft
  • Built 1939

  Last Sold Summary

  • 6% Below List Price
  • $204/SF
  • 82 Days On Market

  Current Estimated Value $305,713

  Last Listing Agent Nicole Blass Raynard & Peirce Realty,LLC

  7 Lawrence Ave, Canaan, CT 06018
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  Est $489,725 Not Listed For Sale

  32 Housatonic Ave, Canaan, CT 06018

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft
  • Built 2003

  32 Housatonic Ave, Canaan, CT 06018

  Last Sold Summary

  • 23% Above List Price
  • $171/SF
  • 28 Days On Market

  Last Sold Price $399,000

  Last Listing Agent Nicole Blass Raynard & Peirce Realty,LLC
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  $120,000

  • Land
  • 5.41 Acres
  • $22,181 per Acre

  00 N Elm St, Canaan, CT 06018

  Here is a rare chance to own an affordable 5.41 ac parcel of land in North Canaan, a village in the Litchfield Hills. Its Location on a secondary town road offers public utilities from the street. The wooded lot shares a border with CT State land and is accessed by a deeded right of way. Just minutes from what both Litchfield and Berkshire counties offer - shopping, outdoor activities, fine

  MICHAEL CONLOGUE William Pitt Sotheby's Int'l

  00 N Elm St, Canaan, CT 06018
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  $454,000 Sold Aug 15, 2025

  100 Sand Rd, Canaan, CT 06018

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1993

  Last Sold Summary

  • 21% Below List Price
  • $234/SF
  • 267 Days On Market

  Current Estimated Value $511,987

  Last Listing Agent Carol Staats Elyse Harney Real Estate

  100 Sand Rd, Canaan, CT 06018
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  Est $162,427 Not Listed For Sale

  72 N Elm St Unit 2E, Canaan, CT 06018

  • 1 Bed
  • 1 Bath
  • 714 Sq Ft
  • Built 1989

  72 N Elm St Unit 2E, Canaan, CT 06018

  Last Sold Summary

  • $228/SF
  • 6 Days On Market

  Last Sold Price $163,000

  Last Listing Agent Hiram Colon Real Broker CT, LLC
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  $595,000 Under Contract

  • 5 Beds
  • 3 Baths
  • 2,750 Sq Ft

  26 Granite Ave, Canaan, CT 06018

  This North Canaan home in town boasts a spacious Main Home along with a Guest House situated on a 1.32-acre lot. The 5-Bedroom Main House is bathed in sunlight and features a lovely flow on the main floor that seamlessly connects a formal Living Room with a fireplace, a Media Room, an Office, the Dining Room, and a Kitchen with a Breakfast Bar that overlooks the backyard. The generous ceiling

  Holly Leibrock Elyse Harney Real Estate

  26 Granite Ave, Canaan, CT 06018
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  $630,000 Sold Aug 25, 2025

  27 Tobey Hill Rd, Canaan, CT 06018

  • 5 Beds
  • 3 Baths
  • 3,436 Sq Ft
  • Built 1790

  Last Sold Summary

  • 3% Below List Price
  • $183/SF
  • 73 Days On Market

  Current Estimated Value $652,226

  Last Listing Agent Tommy Connors Redfin Corporation

  27 Tobey Hill Rd, Canaan, CT 06018
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  Est $191,681 Not Listed For Sale

  70 Church St Unit A2, Canaan, CT 06018

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Built 1990

  70 Church St Unit A2, Canaan, CT 06018

  Last Sold Summary

  • 32% Above List Price
  • $134/SF
  • 48 Days On Market

  Last Sold Price $145,000

  Last Listing Agent Bob Giumarro Giumarro Real Estate
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  /39

  $274,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,616 Sq Ft

  65 E Main St, Canaan, CT 06018

  Beautifully remodeled 2-bedroom Colonial in North Canaan! This 1,616 sq ft single-family home blends classic charm with modern updates. Set on a spacious 0.33-acre lot with a fenced yard and sloping landscape, the property offers 5 total rooms, 1 full bath, and an updated, bright interior featuring a cozy fireplace, fresh finishes, and contemporary touches throughout. Classic wood siding and a

  Alex King Lock and Key Realty, Inc

  65 E Main St, Canaan, CT 06018
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  $68,000 Sold May 23, 2025

  305 Ashley Falls Rd, Canaan, CT 06018

  • Land
  • 1.2 Acres
  • $56,667 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 326 Days On Market

  Current Estimated Value $67,754

  Last Listing Agent Susan Belmonte Coldwell Banker Realty

  305 Ashley Falls Rd, Canaan, CT 06018
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  Est $481,382 Not Listed For Sale

  15 Marilyn Dr, Canaan, CT 06018

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft
  • Built 1986

  15 Marilyn Dr, Canaan, CT 06018

  Last Sold Summary

  • 1% Above List Price
  • $220/SF
  • 195 Days On Market

  Last Sold Price $475,000

  Last Listing Agent John Harney William Pitt
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  /17

  $359,900

  • 2 Beds
  • 2 Baths
  • 2,127 Sq Ft

  277 Ashley Falls Rd, Canaan, CT 06018

  A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef , a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the

  John Harney William Pitt Sotheby's Int'l

  277 Ashley Falls Rd, Canaan, CT 06018
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  $310,000 Sold Oct 22, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 1,799 Sq Ft
  • Built 1907

  Last Sold Summary

  • 10% Below List Price
  • $172/SF
  • 52 Days On Market

  Current Estimated Value $327,688

  Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC

  Unlisted Address
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  Est $467,262 Not Listed For Sale

  20 Clayton Rd, Canaan, CT 06018

  • 3 Beds
  • 1.5 Baths
  • 1,988 Sq Ft
  • Built 1944

  20 Clayton Rd, Canaan, CT 06018

  Last Sold Summary

  • 20% Above List Price
  • $196/SF
  • 189 Days On Market

  Last Sold Price $390,000

  Last Listing Agent David Mallison William Pitt
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  $235,000 Sold Mar 19, 2026

  24 E Main St, Canaan, CT 06018

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1955

  Last Sold Summary

  • 6% Below List Price
  • $196/SF
  • 59 Days On Market

  Current Estimated Value $241,609

  Last Listing Agent Victor Santana Santana Realty Group LLC

  24 E Main St, Canaan, CT 06018
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  Est $279,449 Not Listed For Sale

  145 Lower Rd, East Canaan, CT 06024

  • 3 Beds
  • 1 Bath
  • 1,447 Sq Ft
  • Built 1850

  145 Lower Rd, East Canaan, CT 06024

  Last Sold Summary

  • 4% Above List Price
  • $186/SF
  • 61 Days On Market

  Last Sold Price $269,500

  Last Listing Agent Karen Grimaldi William Pitt
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  $385,000 Sold Dec 29, 2025

  123 Lower Rd, East Canaan, CT 06024

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 1850

  Last Sold Summary

  • 8% Below List Price
  • $203/SF
  • 115 Days On Market

  Current Estimated Value $383,686

  Last Listing Agent Lauren Freedman Coldwell Banker Realty

  123 Lower Rd, East Canaan, CT 06024

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