Canaan, NY Homes

/40
Est $1,349,642 Not Listed For Sale
- 5 Beds
- 2 Baths
- 3,721 Sq Ft
240 Colane Rd, East Chatham, NY 12060

240 Colane Rd, East Chatham, NY 12060

/33
$869,000
- 3 Beds
- 3 Baths
- 4,377 Sq Ft
1977 State Route 295, Canaan, NY 12029

Live, work & play! Impressive post and best beam conversion offers the character of an earlier era while incorporating contemporary amenities. The exposed hand hewn beams exude a warm, rustic charm. There is an en suite primary plus 2 to 3 additional bedrooms and plenty of room for guests. Once a home to artists, the 15 x 38 studio room is perfect to create & display or convert into a yoga

Linnea VanTassel Country Life Real Estate, LLC

1977 State Route 295, Canaan, NY 12029
/7
$290,000 Sold Aug 01, 2025

0 Route 295, Canaan, NY 12060
- Land
- 32.27 Acres
- $8,987 per Acre
Last Sold Summary
- 15% Below List Price
- 349 Days On Market
Last Listing Agent Natalia de Amorim Preferred Country Properties

0 Route 295, Canaan, NY 12060

/68
Est $733,215 Not Listed For Sale
- 2 Beds
- 3 Baths
- 2,056 Sq Ft
3264 County Route 9, East Chatham, NY 12060

3264 County Route 9, East Chatham, NY 12060

/59
$689,000 Pending
- 3 Beds
- 2 Baths
- 1,914 Sq Ft
1907 County Route 5, Canaan, NY 12029

Discover a hidden oasis in Canaan. This magical, meticulously maintained home is set on 2.8 acres of mature landscape, with European-inspired outdoor spaces designed for tranquility and enjoyment. This quality-built, mid-century cape is move-in ready. The many luxury features includes a complete suite on the upper floor. The updated, eat-in kitchen is a cook's delight, and the grand living room,

Peter Newman Beach & Bartolo Realtors

1907 County Route 5, Canaan, NY 12029
/4
$60,000 Sold May 09, 2025

0 Old Queechy Rd, Canaan, NY 12029
- Land
- 3.12 Acres
- $19,231 per Acre
Last Sold Summary
- 20% Below List Price
- 90 Days On Market
Last Listing Agent Tracy Tassinari Gabel Real Estate

0 Old Queechy Rd, Canaan, NY 12029

/35
Est $737,802 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,134 Sq Ft
319 Shaker Ridge Dr, Canaan, NY 12029

319 Shaker Ridge Dr, Canaan, NY 12029

/3
$214,000
- Land
- 12.5 Acres
- $17,120 per Acre
O Mercer Mountain Rd, Canaan, NY 12029

Perched atop Mercer Mountain in Columbia County's coveted Hudson Valley, this 12.5-acre offering combines privacy, prestige, and possibility. The property includes a 6.5-acre primary homesite along with an additional 6-acre parcel across the road—ideal for a guest house, pool, or barn. From its elevated setting, enjoy western views of the Catskill Mountains, capturing sunsets and seasonal

Nikki Carchedi Stone House Properties, LLC

O Mercer Mountain Rd, Canaan, NY 12029
/19
Sold Feb 07, 2025

156 Upper Queechy Rd, Canaan, NY 12029
- 3 Beds
- 2 Baths
- 1,510 Sq Ft
- Built 1900
Last Sold Summary
- 151 Days On Market
Current Estimated Value $430,481

Last Listing Agent Tracy Tassinari Gabel Real Estate

156 Upper Queechy Rd, Canaan, NY 12029

/16
Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,040 Sq Ft
1091 County Route 5, East Chatham, NY 12060

1091 County Route 5, East Chatham, NY 12060

/16
$465,000
- Land
- 60.13 Acres
- $7,733 per Acre
0 County Rte 5 & I90 Unit 20251524, Canaan, NY 12029

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

0 County Rte 5 & I90 Unit 20251524, Canaan, NY 12029
/7
$229,000 Sold Oct 28, 2025

394 Peaceful Valley Rd, Canaan, NY 12029
- 2 Beds
- 2 Baths
- 1,432 Sq Ft
- Built 1981
Last Sold Summary
- 17% Below List Price
- $160/SF
- 27 Days On Market
Last Listing Agent Kelly Harrison Taconic Valley Real Estate

394 Peaceful Valley Rd, Canaan, NY 12029

/22
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,877 Sq Ft
58 Queechy Shores Rd, Canaan, NY 12029

58 Queechy Shores Rd, Canaan, NY 12029

/64
$12,500,000
- 4 Beds
- 6 Baths
- 6,829 Sq Ft
241 Cunningham Hill Rd, Canaan, NY 12029

A Home like no other. You will simply not find a Property like PIERCE PEAK, anywhere. AIA Award Winning Architectural Design by Burr & Mc Callum, crested upon the summit of Cunningham Hill (site cleared for HELIPAD). Open plan living with Indoor and Outdoor Living Rooms. Gourmet Kitchen, 2 Primary and 2 connnected Loft spaces. 2 Bedroom Guest Quarters (that can sleep 8), and Infinity Pool with

Steven Weisz William Pitt Sothebys Intn'l

241 Cunningham Hill Rd, Canaan, NY 12029
/50
$1,265,000 Sold Aug 04, 2025

169 Cunningham Hill Rd, Canaan, NY 12029
- 3 Beds
- 2 Baths
- 2,142 Sq Ft
- Built 1987
Last Sold Summary
- 3% Below List Price
- $591/SF
- 44 Days On Market
Current Estimated Value $1,154,228

Last Listing Agent Anne Harrison Country Life Real Estate, LLC

169 Cunningham Hill Rd, Canaan, NY 12029

/10
Not Listed For Sale
- 1 Bed
- 0.5 Baths
- 1,050 Sq Ft
215 County 24, Canaan, NY 12029

215 County 24, Canaan, NY 12029

/46
$1,590,000
- 7 Beds
- 5.5 Baths
- 6,005 Sq Ft
126 Shaker Ridge Dr, Canaan, NY 12029

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor

Anthony D'Argenzio Houlihan Lawrence, Inc

126 Shaker Ridge Dr, Canaan, NY 12029
/20
$449,900 Sold May 02, 2025

27 N Valley Rd, Canaan, NY 12029
- 3 Beds
- 3 Baths
- 2,000 Sq Ft
- Built 1998
Last Sold Summary
- 9% Below List Price
- $225/SF
- 42 Days On Market
Current Estimated Value $479,732

Last Listing Agent Carrie Dandridge Find Advisors

27 N Valley Rd, Canaan, NY 12029

/48
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,120 Sq Ft
134 Top of Dean Hill Rd, Canaan, NY 12029

134 Top of Dean Hill Rd, Canaan, NY 12029

/2
$89,000
- Land
- 20 Acres
- $4,450 per Acre
0 Flints Crossing Rd, Canaan, NY 12029

Canaan NY Flints Crossing Rd. This is a 20-50 Acre large parcel (exact acrage to be verified), borders on Massachusetts State Line and beyond. Wooded and open areas. Access to town road must be verified.

David Birch Barns & Farms Realty, LLC

0 Flints Crossing Rd, Canaan, NY 12029
/41
$463,000 Sold May 16, 2025

42 Frisbee St, East Chatham, NY 12060
- 4 Beds
- 2 Baths
- 2,152 Sq Ft
- Built 1925
Last Sold Summary
- 7% Below List Price
- $215/SF
- 145 Days On Market
Current Estimated Value $472,932

Last Listing Agent Rebecca Sullivan KW Platform

42 Frisbee St, East Chatham, NY 12060

/15
Est $1,358,448 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,942 Sq Ft
42 Fern Hill Rd, Canaan, NY 12029

42 Fern Hill Rd, Canaan, NY 12029

/31
$695,000 Pending
- 5 Beds
- 4 Baths
- 3,165 Sq Ft
53 Whitings Pond Rd, Canaan, NY 12029

Whitings Pond Farmhouse is a c.1790 farmhouse set in the heart of Columbia County. Located by Queechy Lake, the home is situated on 75 acres of conserved land and exudes classic farmhouse charm. Arrive at a generous front porch that frames the home's façade. Enter through a half-lite door into a center hall. Wide-plank wood floors run the length of the entry and lead to another half-lite door,

MATTHEW CAREY Rouse + Co Real Estate, LLC

53 Whitings Pond Rd, Canaan, NY 12029
/40
$987,000 Sold Jun 16, 2025

44 Old Queechy Rd, Canaan, NY 12029
- 5 Beds
- 2 Baths
- 3,270 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $302/SF
- 41 Days On Market
Last Listing Agent Anne Harrison Country Life Real Estate, LLC

44 Old Queechy Rd, Canaan, NY 12029

/2
Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,800 Sq Ft
2050 County Route 5, Canaan, NY 12029

2050 County Route 5, Canaan, NY 12029

/27
$416,690
- 3 Beds
- 3 Baths
- 2,260 Sq Ft
33 Dermody Rd, Canaan, NY 12029

How about some privacy! This three bedroom, three bath home has lots of privacy and elbow room to play and relax. There is a cathedral ceiling flooding light into the kitchen. A country setting tucked away yet close the Berkshires, Tanglewood, skiing and all the culture this area has to offer. A Finished lower level adds great space for movie watching or quiet contemplation as well as a 12ft by

Ryan Lane Gilcrest Properties

33 Dermody Rd, Canaan, NY 12029
$895,000 Sold Jul 23, 2025

598 County Route 24, Canaan, NY 12060
- 3 Beds
- 3 Baths
- 2,048 Sq Ft
- Built 1975
Last Sold Summary
- 6% Below List Price
- $437/SF
- 51 Days On Market
Last Listing Agent Simone Consor Corcoran Country Living

598 County Route 24, Canaan, NY 12060

/28
Est $869,276 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,659 Sq Ft
98 Goetz Rd, East Chatham, NY 12060

98 Goetz Rd, East Chatham, NY 12060

/30
$425,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
92 Cunningham Hill Rd, Canaan, NY 12029

Shangri La. Perfect country cottage tucked on a private 4.69 acre piece of usable land off a quiet dirt road. Open floor plan with kitchen and eating area moving into the great room with cathedral ceilings. Wood fireplace at the center perfect for apres ski or cozy fall and winter nights. Doors to an oversized deck overlooking the firepit and private grounds and view. Large primary suite with

Tracy Tassinari Gabel Real Estate

92 Cunningham Hill Rd, Canaan, NY 12029
/17
$90,000 Sold Oct 23, 2025

2320 Route 295, Canaan, NY 12060
- Land
- 7.9 Acres
- $11,392 per Acre
Last Sold Summary
- 9% Below List Price
Last Listing Agent Ryan Lane Gilcrest Properties

2320 Route 295, Canaan, NY 12060

/16
Not Listed For Sale
L15 New York 295, Canaan, NY 12029

L15 New York 295, Canaan, NY 12029

/46
$955,000
- 4 Beds
- 2.5 Baths
- 2,100 Sq Ft
308 Shaker Ridge Dr, Canaan, NY 12029

MAJOR PRICE IMPROVEMENT TO SELL!! Discover your own private sanctuary! Nestled in the woods, enjoy breathtaking Queechy Lake views from every level. Relax or entertain on spacious decks. Perfect retreat or full-time living with lake rights. The open floorplan floods the main living area with light and views. 3 bedrooms, a full bath on the bottom floor. The main bedroom ensuite on the top floor

Leonard Brown Berkshire Hathaway HomeService

308 Shaker Ridge Dr, Canaan, NY 12029
/31
$715,000 Sold Aug 25, 2025

70 Reardon York Estates, Canaan, NY 12029
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
- Built 2005
Last Sold Summary
- $378/SF
- 44 Days On Market
Current Estimated Value $713,214

Last Listing Agent Shaina Marron Houlihan Lawrence Inc.

70 Reardon York Estates, Canaan, NY 12029

/8
Not Listed For Sale
L38.1 Beebe Pond Rd, Canaan, NY 12029

L38.1 Beebe Pond Rd, Canaan, NY 12029

/8
$149,900
- 3 Beds
- 1.5 Baths
- 1,372 Sq Ft
1169 New York 295, East Chatham, NY 12060

Opportunity awaits. This 3 bedroom, 1.1 bath Dutch Colonial home offers 1372sf of living space and is ready for it's next chapter. Home needs fair amount of renovation and will be cash only, sold ''as-is.'' Good sized living room with separate dining space, kitchen with good space , first floor bathroom is a full bath. Enclosed rear porch, and nice front porch. 2nd floor has 3 bedrooms, with

Brian Brosen eXp Realty

1169 New York 295, East Chatham, NY 12060
/36
$960,000 Sold Apr 22, 2025

41 Warner Crossing Rd, Canaan, NY 12029
- 4 Beds
- 2.5 Baths
- 3,415 Sq Ft
- Built 1814
Last Sold Summary
- 29% Below List Price
- $281/SF
- 314 Days On Market
Current Estimated Value $1,245,632

Last Listing Agent Natalia de Amorim Preferred Country Properties

41 Warner Crossing Rd, Canaan, NY 12029

Est $880,125 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
134 Cunningham Hill Rd, Canaan, NY 12029

134 Cunningham Hill Rd, Canaan, NY 12029

/5
$89,000
- Land
- 5 Acres
- $17,800 per Acre
155 Shaver, Canaan, NY 12029

Ideal location for commercial or residential construction or combination of both. Site is close to junction of Routes 22 and 295 and Queechy Lake. Access to the Berkshires (Richmond & Tanglewood) and New Lebanon and Rensselaer County & Jiminy Peak. Lots of gravel on property. Zoned commercial (C-2) Close to Massachusetts & Berkshires.

David Birch Barns & Farms Realty, LLC

155 Shaver, Canaan, NY 12029
/46
$750,000 Sold Aug 22, 2025

344 Peaceful Valley Rd, Canaan, NY 12029
- 4 Beds
- 2 Baths
- 2,910 Sq Ft
- Built 1790
Last Sold Summary
- 5% Below List Price
- $258/SF
- 47 Days On Market
Current Estimated Value $758,174

Last Listing Agent Nancy Cuddihy STONE HOUSE PROPERTIES, LLC

344 Peaceful Valley Rd, Canaan, NY 12029

/9
Not Listed For Sale
Unlisted Address

Unlisted Address

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New York Columbia County Canaan

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