Canaan, NY Homes

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  /46

  $841,500

  • 3 Beds
  • 3.5 Baths
  • 3,204 Sq Ft

  2205 County Route 5, Canaan, NY 12029

  HIGHLY MOTIVATED SELLER! Set atop a gentle hill along a quiet, winding county road, this charming New England saltbox home offers a rare blend of timeless elegance and modern comfort. Built in 1995 by a skilled contractor as a spec project, the home was thoughtfully customized to suit a relaxed yet refined lifestyle. With two spacious bedrooms, a cozy den that doubles as a convenient ground-floor

  

  DeWayne A. Powell

  William Pitt Sotheby's Int'l

  (518) 919-3022

  2205 County Route 5, Canaan, NY 12029
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  /29

  $5,600 per month

  • 4 Beds
  • 2 Baths
  • 2,540 Sq Ft
  • House for Rent

  121 Queechy Lake Dr, Canaan, NY 12029

  This newly renovated lakefront home on Queechy Lake is an inviting Upstate New York escape for any season. Set in the foothills of the Berkshires, the post-and-beam 4-bedroom house offers direct lake access, a brand-new wraparound deck for grilling and sunset watching, and plenty of space to unwind. In the warmer months, enjoy the crystal-clear water with your own private dock just across the

  Kelcey Otten Compass Greater NY, LLC d/b/a

  121 Queechy Lake Dr, Canaan, NY 12029
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  /58

  $888,000 Sold Dec 15, 2025

  131 Mercer Mountain Rd, East Chatham, NY 12060

  • 4 Beds
  • 2.5 Baths
  • 2,681 Sq Ft
  • Built 1988

  Last Sold Summary

  • 13% Above List Price
  • $331/SF
  • 11 Days On Market

  Last Listing Agent Deborah Smith Coldwell Banker Prime

  131 Mercer Mountain Rd, East Chatham, NY 12060
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  /2

  Est $983,395 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  43 Shaker Ridge Dr, Canaan, NY 12029

  43 Shaker Ridge Dr, Canaan, NY 12029
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  /21

  $439,000

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  13149 New York 22, Canaan, NY 12029

  Welcome to 13149 NY 22, Canaan, NY 12029—a beautifully updated 3-bedroom, 1.5-bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient

  Jessie Bennett William Pitt Sothebys Intn'l

  13149 New York 22, Canaan, NY 12029
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  /11

  $4,850 per month

  • 3 Beds
  • 3.5 Baths
  • 2,344 Sq Ft
  • House for Rent

  208 Cunningham Hill Rd, Canaan, NY 12029

  Down a beautiful country road lies this fully furnished, completely renovated 3-bedroom, 3.5 bath home--the perfect blend of comfort and countryside charm. Conveniently located between Chatham, NY and The Berkshires, you'll enjoy easy access to fine restaurants, skiing and year-round cultural attractions. Home rental includes access to Queechy Lake.Features include:Central AC,

  Janet Kain The Kinderhook Group, Inc.

  208 Cunningham Hill Rd, Canaan, NY 12029
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  /2

  $1,050,000 Sold Oct 27, 2025

  54 Mercer Mountain Rd, East Chatham, NY 12060

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $417/SF
  • 135 Days On Market

  Last Listing Agent Peter Newman Beach & Bartolo Realtors

  54 Mercer Mountain Rd, East Chatham, NY 12060
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  /5

  Not Listed For Sale

  0 Barnegat Rd, East Chatham, NY 12060

  0 Barnegat Rd, East Chatham, NY 12060
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  /14

  $249,000

  • Land
  • 17.05 Acres
  • $14,604 per Acre

  13191 Route 22 Stop #80, Canaan, NY 12029

  17 private, secluded acres located on a quiet private road in Canaan, NY. The property features frontage on Flat Brook, multiple potential house sites with beautiful views, and mature woods throughout.Electric has already been pulled to the property, making it ready for building. The land is ideal for a primary residence, second home, or small retreat.Quiet, peaceful setting just

  Jessie Bennett William Pitt Sothebys Intn'l

  13191 Route 22 Stop #80, Canaan, NY 12029
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  /43

  $890,000 Sold Jul 15, 2025

  192 Old Queechy Rd, Canaan, NY 12029

  • 4 Beds
  • 2.5 Baths
  • 2,245 Sq Ft
  • Built 2001

  Last Sold Summary

  • 24% Below List Price
  • $396/SF
  • 239 Days On Market

  Last Listing Agent Jean Howard RE/MAX Solutions - Troy

  192 Old Queechy Rd, Canaan, NY 12029
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  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 5,537 Sq Ft

  104 Black Bridge Rd, East Chatham, NY 12060

  104 Black Bridge Rd, East Chatham, NY 12060
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  /40

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  1476 County Route 5, Canaan, NY 12029

  Set on three peaceful acres along a quiet country road, this 3-bedroom ranch home captures the very best of Upstate living. With long views of the Berkshire Hills as the backdrop from your in-ground pool, the 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also less than 30 minutes

  Chris Getman Houlihan Lawrence Inc.

  1476 County Route 5, Canaan, NY 12029
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  /27

  $530,000 Sold Apr 22, 2025

  116B Cunningham Hill Rd, Canaan, NY 12029

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Above List Price
  • $405/SF
  • 18 Days On Market

  Current Estimated Value $567,166

  Last Listing Agent Jessie Bennett William Pitt Sothebys Intn'l

  116B Cunningham Hill Rd, Canaan, NY 12029
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  /36

  Est $1,248,500 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,760 Sq Ft

  13191 State Route 22 Unit 27, Canaan, NY 12029

  13191 State Route 22 Unit 27, Canaan, NY 12029
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  /26

  $725,000

  • 2 Beds
  • 2 Baths
  • 2,366 Sq Ft

  156 Mercer Mountain Rd, East Chatham, NY 12060

  A magical spot 1500' above sea level and offering spectacular 75 mile long views of the Catskill Mountains! Modern home with floor to ceiling windows to soak in the views while enjoying the warmth of the fireplace. Clean lines and open floor plan. Two bedrooms plus a finished room w/closet in the walk-out basement. A one of a kind property located minutes to the Berkshires, Chatham, Hudson, or

  Terry Cozzolino Cozzolino Real Estate Inc

  156 Mercer Mountain Rd, East Chatham, NY 12060
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  /34

  $429,000 Sold Mar 28, 2025

  14 Cunningham Hill Rd, Canaan, NY 12029

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  Last Sold Summary

  • $298/SF
  • 6 Days On Market

  Current Estimated Value $453,445

  Last Listing Agent Cole Cioffi Weichert Realtors-Reliable Properties

  14 Cunningham Hill Rd, Canaan, NY 12029
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  /34

  Est $588,802 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft

  365 County Route 24, East Chatham, NY 12060

  365 County Route 24, East Chatham, NY 12060
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  /10

  $1,880,000

  • 4 Beds
  • 1 Bath
  • 1,443 Sq Ft

  105 Norton Rd, Unknown Ny City, NY 12029

  Incredible opportunity to own 367 acres of privacy with your own 6-acre lake, trails, streams, and direct access to Beebe Hill State Forest and its 30 miles of hiking trails. The property includes a classic single-family home (ready for a full renovation), a 40' x 50' Morton shed, and a heated garden shed.An approved second homesite with septic, underground electric/data lines, and a transformer

  Nikki Carchedi STONE HOUSE PROPERTIES, LLC

  105 Norton Rd, Unknown Ny City, NY 12029
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  /7

  $290,000 Sold Aug 01, 2025

  L50.1 New York 295, Canaan, NY 12029

  • Land
  • 32.27 Acres
  • $8,987 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 293 Days On Market

  Last Listing Agent Natalia de Amorim Preferred Country Properties

  L50.1 New York 295, Canaan, NY 12029
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  /29

  Est $806,762 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,336 Sq Ft

  2142 County Route 5, Canaan, NY 12029

  2142 County Route 5, Canaan, NY 12029
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  /18

  $335,000 Pending

  • Land
  • 7.07 Acres
  • $47,383 per Acre

  13191 Route 22 Stop #20, Canaan, NY 12029

  7 Acres of Prime Farmland with Barns in Canaan, NYLooking to start or grow your farm? This 7-acre parcel right on State Route 22 in Canaan has everything you need to hit the ground running. The fields have a high pH level--great for growing crops--and there's a reliable well on site producing 8 gallons per minute.You'll also find two solid barns with newer roofs (just 5 years old), perfect for

  Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  13191 Route 22 Stop #20, Canaan, NY 12029
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  /23

  $539,900 Sold Jul 09, 2025

  22 Paige Rd, Canaan, NY 12029

  • 4 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1910

  Last Sold Summary

  • $568/SF
  • 52 Days On Market

  Last Listing Agent Elisha Poirier STONE HOUSE PROPERTIES, LLC

  22 Paige Rd, Canaan, NY 12029
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  /45

  Est $787,756 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  129 Barnegat Rd, East Chatham, NY 12060

  129 Barnegat Rd, East Chatham, NY 12060
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  /17

  $465,000

  • Land
  • 60.13 Acres
  • $7,733 per Acre

  L21.3 County Route 5 & I90, Canaan, NY 12060

  Nestled in the coveted Taconic Mountains, known for their rugged beauty, rich wildlife, clear streams, and hidden ponds, this double parcel boasts over 60 acres in Canaan, NY offering both accessibility and seclusion. The Taconics create a tranquil, less-traveled alternative to the busier Berkshires, offering privacy, natural beauty, and easy access to state forests and rural charm. The front 15+

  Jessica Coutsonikas KW Platform

  L21.3 County Route 5 & I90, Canaan, NY 12060
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  /32

  $375,000 Sold Aug 20, 2025

  70 Miller Rd, Canaan, NY 12029

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1947

  Last Sold Summary

  • 7% Above List Price
  • $375/SF
  • 14 Days On Market

  Current Estimated Value $370,120

  Last Listing Agent Thomas Pawlowski Four Seasons Sotheby's Int.

  70 Miller Rd, Canaan, NY 12029
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  /36

  Est $1,211,368 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,261 Sq Ft

  104 Ridge Rd, East Chatham, NY 12060

  104 Ridge Rd, East Chatham, NY 12060
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  /45

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,920 Sq Ft

  3124 County Route 9, East Chatham, NY 12060

  Modern Country FarmhouseBuilt to pamper its proud owner by offering a quiet, peaceful and very private get away w/ cathedral ceiling living room semi open to wonderfully equipped kitchen and breakfast area. Primary ensuite is spacious and bright -- offers all amenities you would ever wish for from a walk in closet, to bath with double vanity, Jacuzzi soaking tub, separate shower, separate toilet

  Natalia de Amorim PREFERRED COUNTRY PROPERTIES

  3124 County Route 9, East Chatham, NY 12060
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  /49

  $585,000 Sold May 30, 2025

  627 County Road 24, East Chatham, NY 12060

  • 4 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • Built 1790

  Last Sold Summary

  • 16% Below List Price
  • $352/SF
  • 284 Days On Market

  Current Estimated Value $607,373

  Last Listing Agent Rochelle Bartolo Beach & Bartolo Realtors

  627 County Road 24, East Chatham, NY 12060
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  /36

  Est $336,399 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  13249 State Route 22, Canaan, NY 12029

  13249 State Route 22, Canaan, NY 12029
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  /36

  $725,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft

  605 County Route 24, East Chatham, NY 12060

  This historic home was constructed by Thomas Bishop, a veteran of the War of 1812 in the early 1800's and was once known as Bishop's Tavern. It began as an inn and tavern on what was once, the Stockbridge and Hudson stagecoach line. Since then it has been lovingly tended and updated with an eye to preservation.Located on a quiet country road in Red Rock and surrounded by mature gardens and

  Barbara Conkling Houlihan Lawrence, Inc.

  605 County Route 24, East Chatham, NY 12060
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  $900,000 Sold Jan 17, 2025

  585 County Route 5, East Chatham, NY 12060

  • 3 Beds
  • 1.5 Baths
  • 1,795 Sq Ft
  • Built 1904

  Last Sold Summary

  • 8% Below List Price
  • $501/SF
  • 76 Days On Market

  Last Listing Agent Deborah Cuiffo Coldwell Banker Realty

  585 County Route 5, East Chatham, NY 12060
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  Est $396,653 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,482 Sq Ft

  187 Tunnel Hill Rd, Canaan, NY 12029

  187 Tunnel Hill Rd, Canaan, NY 12029
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  /28

  $795,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 9,405 Sq Ft

  165 Queechy Lake Dr, Canaan, NY 12029

  Fall in love with this Queechy Lake opportunity - where the lake itself is considered one of the most pristine lakes in New York state! An amazing lakefront property where the views continue far beyond the distant shores. With a combined total land area of just over 9 acres; spanning two parcels and with over 100' of private shoreline, the possibilities seem endless. The original motel and use

  Michael Stasi Corcoran Country Living

  165 Queechy Lake Dr, Canaan, NY 12029
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  /32

  $880,000 Sold Aug 21, 2025

  72 Old Queechy Rd, Canaan, NY 12029

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Above List Price
  • $367/SF
  • 99 Days On Market

  Current Estimated Value $875,850

  Last Listing Agent Raj Kumar Four Seasons Sotheby's International Realty

  72 Old Queechy Rd, Canaan, NY 12029
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  /31

  Est $636,742 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,111 Sq Ft

  70 Lillie Rd, Canaan, NY 12029

  70 Lillie Rd, Canaan, NY 12029
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  /14

  $160,000

  • Land
  • 7.68 Acres
  • $20,833 per Acre

  400 Mercer Mountain Rd, East Chatham, NY 12060

  Welcome to Mercer Mountain—an exclusive enclave of million-dollar-plus homes nestled in the rolling Taconic Mountains of Columbia County. Perfectly situated between the world-class cultural offerings of the Berkshires and the awe-inspiring Catskill Mountains, this remarkable 7.68-acre parcel offers a rare opportunity to build your dream estate toward the very end of the road in one of the Hudson

  Callan Bergmann Compass Greater NY, LLC

  400 Mercer Mountain Rd, East Chatham, NY 12060
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  /49

  $650,000 Sold Jul 22, 2025

  116 Cunningham Hill Rd, Canaan, NY 12029

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1960

  Last Sold Summary

  • $203/SF
  • 47 Days On Market

  Current Estimated Value $1,047,513

  Last Listing Agent Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  116 Cunningham Hill Rd, Canaan, NY 12029
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  /50

  Est $1,140,102 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,400 Sq Ft

  3 Twin Brook Rd, East Chatham, NY 12060

  3 Twin Brook Rd, East Chatham, NY 12060
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  /51

  $2,000,000

  • 3 Beds
  • 3 Baths
  • 3,030 Sq Ft

  3243 County Route 9, East Chatham, NY 12060

  Welcome to Bear Paw Creek. Explore this captivating 24.68-acre retreat in East Chatham, New York, where a private drive leads to an idyllic blend of historic charm and contemporary elegance in an 1825 farmhouse. Featured in Domino Magazine this designer home is nestled amid rolling pastoral valleys, dense woods, and a gently flowing stream, the property unfolds with sublime gardens, a unique

  Patrick Heffernan Compass Greater NY, LLC

  3243 County Route 9, East Chatham, NY 12060
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  /7

  $290,000 Sold Aug 01, 2025

  0 New York 295, Canaan, NY 12029

  • Land
  • 32.27 Acres
  • $8,987 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 364 Days On Market

  Last Listing Agent Natalia de Amorim PREFERRED COUNTRY PROPERTIES

  0 New York 295, Canaan, NY 12029

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