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Canaan, NY Homes for Sale with Acreage

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  • /66

    $1,300,000

    • 3 Beds
    • 3.5 Baths
    • 2,935 Sq Ft

    21 Stone House Rd, Canaan, NY 12029

    Welcome to this thoughtfully designed home with south facing views on 3 serene acres. The home was constructed by a local builder and offers a perfect blend of luxury and privacy. Situated on the Canaan/New Lebanon line, it boasts breathtaking views and an in-ground pool ideal for relaxation and entertainment on the blue stone patio. The spacious first-floor primary suite provides a peaceful

    Melissa Dimassimo Stone House Properties, LLC

    21 Stone House Rd, Canaan, NY 12029
  • /32

    $949,000

    • 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 forguests. Once a home to artists, the 15 x 38 studio room is perfect to create & display or convert into a yoga

    Philip Feiner Country Life Real Estate

    1977 State Route 295, Canaan, NY 12029
  • /69

    $1,590,000

    • 7 Beds
    • 5.5 Baths
    • 7,316 Sq Ft

    126 Shaker Ridge Dr, Canaan, NY 12029

    Berkshire/New York Contemporary Estate CHECK OUT VIRTUAL TOURS #2, & #3. 4616 sf Main Home (3100 + 1516 +storage) + 2700sf Guest Residence on 20 private acres (3 lots) in Shaker Ridge. Soaring spaces and beautiful stone fireplaces, master suite w. fireplace, plus junior suite and third BR or studio with sink. Large kitchen with informal dining area & lounge with fireplace, plus, great room with

    David Birch Barns & Farms Realty, LLC

    126 Shaker Ridge Dr, Canaan, NY 12029
  • /46

    $955,000

    • 4 Beds
    • 2.5 Baths
    • 1,689 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
  • /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
  • /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
  • /33

    $595,000

    • 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
  • /23

    $1,725,000

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    388 Maple Dr, East Chatham, NY 12060

    If you love to drive long gravel roads through maplewood forests dotted with antique farmhouses and barns, we have this offering located in the corner of Columbia County that serves mountaintop views across the Hudson Valley. The impressive drive into the property through the gate is uphill past three meadows ablaze in native wildflowers across three seasons and through its own maple stock. The

    Parker Meyer Four Seasons Sotheby's Int.

    388 Maple Dr, East Chatham, NY 12060
  • /51

    $2,400,000

    • 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
  • /3

    $250,000

    • Land
    • 6.02 Acres
    • $41,528 per Acre

    590 County Route 24, Canaan, NY 12060

    Six Acres of open and wooded land located in the desirable Red Rock area of Canaan. This raw land offers an excellent opportunity for buyers ready to bring their vision to life. A deeded right of way along the Narrows Road is available for this property. The Indian Creek runs through the rear of the parcel. A right of first refusal for this property is being given to the buyers of the

    Barbara Conkling Houlihan Lawrence, Inc.

    590 County Route 24, Canaan, NY 12060
  • /36

    $725,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /45

    $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. 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,

    DeWayne A. Powell WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    2205 County Route 5, Canaan, NY 12029
  • /17

    $782,000

    • 2 Beds
    • 2 Baths
    • 1,616 Sq Ft

    156 Mercer Mountain Rd, East Chatham, NY 12060

    A magical spot 1500' above sea level and offering 75 mile long views of the Catskill Mountains! Modern home with floor to ceiling windows to soak in the views while toasting toes in front 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 Albany

    Terry Cozzolino Cozzolino Real Estate Inc

    156 Mercer Mountain Rd, East Chatham, NY 12060
  • /46

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,907 Sq Ft

    18 Old Queechy Rd, Canaan, NY 12029

    RENOVATED ANTIQUE COLONIAL situated on expansive rolling bucolic property with mountain views. The house is located on a tree-lined country road, and is conveniently located between the towns of West Stockbridge and Chatham and within close proximity to Lenox and Tanglewood. The first floor of the house has an airy foyer with a wood-stove, formal dining room, fully modernized open-layout kitchen

    Tom Lynch COMPASS MASSACHUSETTS , LLC GB

    18 Old Queechy Rd, Canaan, NY 12029
  • /17

    $4,700,000

    • Land
    • 412 Acres
    • $11,408 per Acre

    69 County Rte 24, Chatham, NY 12037

    412 acre rare and enchanting paradise. A long gated driveway framed by mature maples & ancient stonewalls lead you over a bridge gently ascending through the woods and breaking open to rolling fields and stunning Catskill Mountain views. A perfect quiet spot to watch the firey evening sunsets while reflecting on the days end. Follow the path a bit further - winding through the Birch grove and

    Anne Harrison Country Life Real Estate, LLC

    69 County Rte 24, Chatham, NY 12037
  • /18

    $335,000

    • 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
  • /12

    $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 in one of the Hudson Valley’s most sought-after

    Callan Bergmann Compass Greater NY, LLC

    400 Mercer Mountain Rd, East Chatham, NY 12060
  • /27

    $419,000

    • 3 Beds
    • 3 Baths
    • 1,460 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
  • /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
  • /53

    $1,275,000

    • 7 Beds
    • 7 Baths
    • 3,896 Sq Ft

    91 & 95 Miller Rd, Canaan, NY 12029

    Last Chance to own a Storybook Historic Estate on 10+ Bucolic Acres in Canaan, NY Offered for the first time in over 40 years, this timeless 10.7-acre estate is the ultimate countryside escape—just 2.5 hours from NYC and 2 hours from Boston. Nestled between the Berkshires and Hudson Valley, the property features two fully restored historic homes that blend 18th- and 19th-century charm

    Jessie Bennett William Pitt Sothebys Intn'l

    91 & 95 Miller Rd, Canaan, NY 12029
  • /48

    $599,000

    • 3 Beds
    • 3 Baths
    • 1,450 Sq Ft

    95 Miller Rd, Canaan, NY 12029

    This fully renovated 1890 farmhouse on 7.9 acres offers the perfect blend of historic charm and modern convenience. Located on a quiet country road in Canaan, NY, the home features original exposed beams, wide plank floors, and a thoughtfully updated kitchen and dining area (2023). The layout includes 3 bedrooms and 2 full baths--two bedrooms and a bath on the main floor, including a primary with

    Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    95 Miller Rd, Canaan, NY 12029
  • /39

    $799,000

    • 4 Beds
    • 4 Baths
    • 2,500 Sq Ft

    91 Miller Rd, Canaan, NY 12029

    Knoll Rock - Restored 1700s Farmhouse in Canaan, NY Knoll Rock is a beautifully restored post-and-beam farmhouse dating back to the 1700s, set on 2.79 serene acres in Canaan, New York. This distinctive property seamlessly blends historic charm with modern comforts, offering a rare opportunity to own a piece of early American architecture in a location convenient to both the Berkshires and Hudson

    Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    91 Miller Rd, Canaan, NY 12029
  • /42

    $835,000

    • 3 Beds
    • 2.5 Baths
    • 2,623 Sq Ft

    25 Ridge Rd, East Chatham, NY 12060

    Exceptional Views & Elevated ComfortPerched high above Mercer Road at the top of Ridge, this stunning 2,600+ sq ft contemporary home offers panoramic views that stretch across the valley to the Catskills—some of the best in the region. Set on 10 private acres, the home pairs modern ease with total tranquility.The vaulted great room, anchored by a floor-to-ceiling wood-burning

    Baris Demirel Serhant LLC

    25 Ridge Rd, East Chatham, NY 12060
  • /19

    $465,000

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

    0 County Route 5 & I90 Unit 202517807, 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

    0 County Route 5 & I90 Unit 202517807, Canaan, 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
  • /33

    $1,900,000

    • 9 Beds
    • 8 Baths
    • 6,967 Sq Ft

    Tbd Ny-22, Canaan, NY 12029

    We are proud to offer this extraordinary historical property comprised of two Shaker built homes dating to 1854, situated on 344 acres. In addition to the two residences are two barns and a screened gazebo. Both houses face a 40 acre + or - open field and one of the most notable hillsides that identify the region as Shaker Valley. The land continues up and over the top of the mountain with a peak

    Fred Waring Corcoran Country Living

    Tbd Ny-22, Canaan, NY 12029
  • /47

    $599,999

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    263 Old Hudson Turnpike, Canaan, NY 12029

    NEW PRICE!! Top area builder. All brand new eyebrow colonial transformed in to a modern energy efficient home with 3 bedrooms and 2 full baths. New Anderson windows, doors, roof, insulation, Smart siding. All new lighting throughout the house, new floors. All brand new appliances. Literally Brand new everything. Conservancy across the road to further protect against development.New hot water

    Sharon McArdle Berkshire Hathaway Home Services Blake

    263 Old Hudson Turnpike, Canaan, NY 12029
  • /24

    $1,880,000

    • Land
    • 367 Acres
    • $5,123 per Acre

    105 Norton Rd, Canaan, NY 12037

    Discover 367 acres of serene privacy, complete with your own 6-acre lake, meandering trails, and gentle streams. Imagine building your dream home or a family retreat, all nestled in and embraced by nature. For even more adventure and hiking opportunities, this land is bordered by the expansive 2,000-acre Beebe Hill State Forest. Come experience the perfect blend of tranquility and recreation.

    Nikki Carchedi Stone House Properties, LLC

    105 Norton Rd, Canaan, NY 12037
  • /15

    $169,000

    • Land
    • 26.5 Acres
    • $6,377 per Acre

    0 County Route 9 Unit 20255066, New Lebanon, NY 12060

    26.5 acres of land to farm or build on . Fabulous views over surrounding farmland, valley and mountains.Great mix of open land & woods . Pond for fishing or irrigation for crops. Beautiful stream & rock walls. Perfect land to put in an agricultural program for lower taxes.Just 2.5 hours from NYC, 35 minutes to Hudson, 30 minutes to Albany, 15 minutes to Pittsfield & Jiminy Peak.

    Anne Harrison Country Life Real Estate, LLC

    0 County Route 9 Unit 20255066, New Lebanon, NY 12060
  • /12

    $212,900

    • Land
    • 4 Acres
    • $53,225 per Acre

    0 Cross Rd, West Stockbridge, MA 01266

    Spectacular 4+/- acre parcel in a peaceful setting. It is backed up to a state conservatory so your privacy will remain in tact! This beautiful parcel is ready for your new home with a recent survey and perc test. Nestled in a tranquil area, that’s close to Card Pond and downtown Lenox. Come develop your dream home on this private parcel, but yet still be near all of the local attractions and

    Kimber Bradley Robin Delaney Real Estate

    0 Cross Rd, West Stockbridge, MA 01266
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