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43 Homes For Sale in Canaan, NY

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$69,000Est. Payment
20.6 Acres
27 Queechy Lake Drive, Canaan, NY 12029
Lots Land For Sale

Large parcel with deeded shared access to 275' frontage on Queechy Lake and common driveway. Build your beautiful dream house or vacation home here!

$589,000Est. Payment
4 Beds | 3 Baths | -- Sqft
268 Vanderberg Rd, Canaan, NY 12029
House For Sale

You truly have to see it to believe it. Outstanding, picturesque views of the Catskill Mountains and beyond.There is nothing quite like the sun setting over the gentle hills in the valley and the trees on the peaks when on an outdoor deck facing west. This rustic, yet spotless, beautiful 3000 square foot A-Frame has 4 bedrooms and 3 bathrooms. Whether it's skiing nearby at one of the local resorts in the wintertime, lounging by the nearby beach in summertime, or seeing the breathtaking foliage in autumn, this house provides you with all. On 7 Acres of land, rejoice in total privacy and be able to live in luxury fit to unwind. If you do need to work, high speed internet of up to 1,000 MBPS is available along with satellite television. This house is unlike any other. Whether it's you,

$195,000Est. Payment
10 Acres
4 Madison Avenue, East Chatham, NY 12029
Lots Land For Sale

One of the most dramatically sited pieces of land available in Columbia County with 270 degree views sitting on top of a mountain in an enclave surrounded by large gorgeous properties and still completely private. Next to Mercer mountain. Views include the Catskills, Albany city skyline and the Berkshires. 10 min. to Chatham, 25 min. to Hudson, Great Barrington, Lenox and less than 2.5 hrs to NYC and Boston.

$440,000Est. Payment
3 Beds | 2 Baths | 680,843 Sqft
306 Tunnel Hill Rd, Canaan, NY 12029
House For Sale

Beautiful 200+ year-old eyebrow colonial farmhouse with rocking chair porch on 15+ acres with large pond. This home boasts lots of distinguishing character throughout such as exposed beams, wood floors and baths (2) renovated to today's fine standards. Two well-sized bedrooms upstairs and a den on the first floor that could easily be used for guests or as an office. Generous living, dining and kitchen areas make this an easy-living charmer. A large barn with a huge bonus studio/workspace offer many options for your imagination. Just under 20 minutes to Lenox in the heart of the Berkshires, under 20 minutes to adorable Chatham Village, within 30 minutes of four popular ski areas, and 15 minutes to the TSP. Access to Queechy Lake with swimming beach. Country living at its best.

$1,400,000Est. Payment
3 Beds | 4 Baths | 4,000 Sqft
121 Top Of Dean Hill Rd, Canaan, NY 12029
House For Sale

This sophisticated Modernist retreat was created by two prominent colleagues of Frank Lloyd Wright: they combined stonework techniques pioneered at Taliesin West with Usonian design and a soaring peaked roof, which Wright used in church architecture: in this spectacular setting, that roof-line is a paean to nature. Expansive windows, honed granite flooring with radiant heat, and polished wood finishes combine with rugged concrete and stone and a seamless flow of indoor/outdoor space to create a setting that is both dramatic and comfortable. Seller improvements include a new chef's kitchen, central AC, and custom details. Set on 17 acres with perennial gardens, woodland paths, stylish separate guest house, and a 3.5-car garage, convenient to the Berkshires and Hudson Valley. A truly exceptional example of mid-century modern.

$199,000Est. Payment
3 Beds | 1 Bath | 1,815 Sqft
13336 New York State Route 22, Canaan, NY 12029
House For Sale

Coveted Canaan! Three bedroom One bath home with lots of elbow room. Over 1800 square feet of living space plus a generous two car garage, workshop, utility room and out buildings scaled for any project. With frame and block construction, this home is solid! New high efficiency propane boiler and auxiliary outdoor wood boiler that can not only heat the house but the pool too! Enjoy watching nature out the windows onto a private back yard. There is a family room to view a 180 degree vantage that just needs some finishing touches. Best of all... Right next to everything the Berkshires have to offer, 30 Minutes from Albany and Historic Hudson. If you are viewing this on a national RE website plz contact listing agent directly.

$2,200,000Est. Payment
367 Acres
105 Norton Road, Canaan, NY 12017
Lots Land For Sale

Rare opportunity to own ~367 stunning acres at the confluence of 2 major crossroads (Route 22 and Route 90). The main entrance leads to an idyllic 8 acre stream fed pond complete with small island, while the western side of the property offers a high elevation building site with spectacular Catskill and Berkshire Taconic Mountain views. (Small older building and 40' x 50' Morton Shed overlooks the pond, with septic and water). Privacy and protection are afforded by both deciduous trees and mature conifers as well as New York State Forest land. Ideally positioned near the border of New York State and Massachusetts, this location allows for 2+/- hour easy access to and from Boston, Albany, New York City and Vermont either from the main entrance or separate service road off of Route 90. Ideal for the sports enthusiast, a weekend retreat or possible commercial use (i.e. - wind farm). This unique location is close to area attractions including Tanglewood, local ski mountains, fine restaurants, inns, antiquing and only 10 minutes to West Stockbridge.

$26,000
$399,000Est. Payment
1 Bed | 4 Baths | 2,999 Sqft
1267 Route 295, Canaan, NY 12060
House For Sale

Property has a one bedroom apartment. Lots of parking. Potential for outdoor deck. Think outside the box for further residential potential perhaps? Successful and well established restaurant & bar on one acre. Completely turn key! Liquor license. Seats approximately 66. ADA compliant. Being sold with all furniture, equipment & inventory. Adjacent to the Klingler Farm. Located on a well traveled main route from Chatham to Canaan. Quick access to Jiminy Peak and the Berkshires. Great investment. A great stop off for the hungry traveler or destination dining for the local resident!

$795,000Est. Payment
4 Beds | 2 Baths | 4,153 Sqft
1977 State Route 295, Canaan, NY 12029
House For Sale

This truly unique building complex, originally constructed in the 1880s,consists of residential and commercial converted barns. The main house is a modern rustic, post and beam home, with one bedroom downstairs, three loft bedrooms upstairs, two new full baths, living room, dining room, kitchen, office, two foyers, a garage, and a workshop. The commercial gallery, currently used as an artist's studio, boasts soaring ceilings and natural light, with separate parking, a separate entrance and it's own heat source. Perfect for the buyer who has a business and is looking for a live/work situation with a high visibility location, close to major highways and has easy access for shipments and deliveries. The third building is a 2-story large garage warehouse space, waiting to be converted into an income apartment, airbnb or guest house. The private back yard has plenty of space for parties and gatherings. The 6 acres of land ascend into a wooded area with potential for construction.

$9,000
$590,000Est. Payment
4 Beds | 4 Baths | 2,478 Sqft
34 Fern Hill, Canaan, NY 12029
House For Sale

Find your Seclusion! This Contemporary home sits quietly on the NY/MA border amidst its 15.8 A of land & offers a wall of glass that will be your window onto your own private world! Drama, fireplace, decks, nature & more all combine for exciting multi-level living with soaring ceiling heights, a living room that is warmed by HW floors & the fireplace with woodstove insert. Fabulous kitchen with plenty of workspace, granite countertops & open flow to the dining room will be your place to visit & entertain, & the office area in-between has plenty of inspiration with views onto the yard. The master bedroom with private bath & balcony is located on this uppermost level plus 2 add'l bedrooms & bath. The lower level boasts a family room area for relaxation, with 4th bedroom, bath & walk-out access to the yard. Summertime will mean relaxing on the covered side porch, BBQ's on the deck, hikes to the top of the mtn for views & outdoor fire pit fun. Garages, Lake rights, close to skiing & more!

$5,000
$279,000Est. Payment
3 Beds | 1 Bath | 1,165 Sqft
1170 State Route 295, Canaan, NY 12060
House For Sale

A house becomes a home, when its owner cares for it and loves everything about it, and continues to improve it. This lovely home is going on the market for first time after current owner purchased it over forty five years ago. Since that time, there have a number of significant upgrades, like the addition a 24x36 three car garage, with a large space above it that could easily be utilized for additional living space. Additional features, include, black top driveway, a screen porch, central air conditioning, a metal roof, large walk-in closet, a generator, and a large shed. Come pay a visit and you may choose to become the new steward to this wonderful home.

$20,000
$245,000Est. Payment
2 Beds | 1 Bath | 1,087 Sqft
13249 State Route 22, Canaan, NY 12029
House For Sale

Canaan Cottage 2 Plus Acres Large Barn. This 2BR cottage has been completely renovated with stone foundation along with a 25 x 40 2 story barn. On 2.6 acres of land all systems are new and it is convenient to the Berkshires and Tanglewood.

$20,000
$245,000Est. Payment
2 Beds | 1 Bath | 1,087 Sqft
13249 State Route 22, Canaan, NY 12029
House For Sale

Canaan Cottage 2 Plus Acres Large Barn. This 2BR cottage with original stone foundation has been completely renovated. Additional 25 x 40 2 story barn. On 2.6 acres of land all systems are new and it is convenient to the Berkshires and Tanglewood.

$5,000
$143,000Est. Payment
14.36 Acres
0 State Route 295, Canaan, NY 12029
Lots Land For Sale

Build your dream house and enjoy the views. Road already in place leading to private driveway with approximately an acre clearing that already has the services pulled to the property. About two and a half hours from NYC and Boston and a half hour from Albany with quick access to the highway. The time is now to star tplanning your private home in the woods.

$25,000
$400,000Est. Payment
4 Beds | 3 Baths | 20,473 Sqft
1641 County Route 5, Canaan, NY 12029
House For Sale

A totally refurbished Center Hall Colonial which still retains some of the character of the 19th century. A list of the amenities includes a large cook's kitchen with top stainless steel appliances, adjoining dining area, pull down projector screen and projector, first floor master suite, 4 bedrooms, 3 full baths, new siding, whirlpool tub, open shower, a number of raised flower beds and glass enclosed patio. One of the 2 car garages currently houses a person-cave (24 x 21) but could just as easily be used as a garage again. Another 2 car garage is located on the lower part of the property with a workshop/studio/artist's office overhead (21 x 31). Located just across the road from the Canaan park. Close to Queechy, your choice of ski resorts, the Berkshires.

$279,000Est. Payment
30.9 Acres
0 New Concord Road, Canaan, NY 12060
Lots Land For Sale

Canaan Land 30 Acres Million Dollar Views. These beautiful rolling, conserved 30 acres is perfect for a family estate with great views. Only minutes from the Village of Chatham the long driveway insures great privacy.

$425,000Est. Payment
12.33 Acres
16 Mercer Mountain Road, Canaan, NY 12029
Lots Land For Sale

Views-Views-Views! You can see 3 states without ever leaving your living room! Spectacular 40 +/- mile Views of the Catskill Mountains, Hudson River Valley, Albany skyline, Green Mountains of Vermont and Berkshire Mountain range from this 200-220 degree view, 12.3 acre vacant prime land parcel on Mercer Mountain, Canaan - one of the highest elevations in Columbia County, New York. Bordering the Massachusetts-NY line in the Berkshires, this parcel has been selectively cleared for house site; mature trees retained & cabled; perc test completed and septic system designed; shale driveway installed; land graded and ready to build. This is a unique parcel of land with fantastic views in three directions in an area of fine homes. Come visit and bring your lunch to take in the views. Close to all Berkshire activities; 15 minutes Tanglewood, Lenox, Stockbridge and Great Barrington; 2.5 hrs NYC & Boston; Hudson & Amtrak 25 minutes. Bring your binoculars too!

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