22

Canaan, NY Houses for Sale

Section Image
  • /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
  • /65

    $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 reputable 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

    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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /51

    $2,400,000 Open Sun 12PM - 2PM

    • 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
  • /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
  • /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
  • /29

    $279,000

    • 2 Beds
    • 1 Bath
    • 1,099 Sq Ft

    28 Upper Queechy Rd, Canaan, NY 12029

    The home you've been looking for! This charming cottage with Queechy Lake rights offers comfortable living with modern amenities! The spacious chef's kitchen is the heart of the home, complemented by a separate living room, dining area, sunroom and bathroom on the first floor. Upstairs, you'll find a primary bedroom with ample space (including a cedar-lined walk-in closet,) a second bedroom, and

    Brian Wagner Beach & Bartolo Realtors

    28 Upper Queechy Rd, Canaan, NY 12029
  • /20

    $479,000

    • 2 Beds
    • 1 Bath
    • 770 Sq Ft

    13 Tremper Property Assn Rd, Canaan, NY 12029

    Vintage 1920 Queechy Lake cottage with deeded right of way to the lake shore. Enjoy complete privacy here at your 4-season getaway. Magical tree-house setting on one full acre with cozy front porch. Turn-key property with hardwood floors, great room with cathedral ceiling, kitchen with dishwasher and washer & dryer, two bedrooms, one bath. Room to expand. A sweet shed for your kayak and bike. A

    Nancy Cuddihy STONE HOUSE PROPERTIES, LLC

    13 Tremper Property Assn Rd, Canaan, NY 12029
  • /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
  • /45

    $650,000

    • 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

    $840,000

    • 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
  • /47

    $699,999

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

    263 Old Hudson Turnpike, Canaan, NY 12029

    PRICE REDUCTION TO SELL!! 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. New hot water heater tank with heat pump, water purification system. New Radon

    Sharon McArdle Berkshire Hathaway Home Services Blake

    263 Old Hudson Turnpike, Canaan, NY 12029
  • /52

    $575,000

    • 5 Beds
    • 3 Baths
    • 3,200 Sq Ft

    105 McNamee Rd, Canaan, NY 12029

    2024 Renovation of Queechy Lake Year Round Private Recreational Retreat on 3 Levels with own private boat launch & beach and minutes to Ski Jiminy. Currently operating as successful Air BNB with separate owner living space. Estimate income with both units rent: 25,000. Brand new furnishings included: ready to go!! Be Sure to Check Out Virtual Media Tour. 3rd floor recently finished . Other floors

    David Birch Barns & Farms Realty, LLC

    105 McNamee Rd, 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
How to Buy a Home How to Finance a Home How to Sell a Home