21

Canaan, NY Houses for Sale

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  • /54

    $1,699,000

    • 4 Beds
    • 3.5 Baths
    • 4,604 Sq Ft

    74 Oak Ridge, Canaan, NY 12029

    74 Oak Ridge, Canaan, NYJust over two hours from both New York City and Boston, this architecturally refined 4-bedroom contemporary sits on 5 private acres along a quiet country road in Columbia County. With panoramic views, elegant design, and effortless indoor-outdoor flow, this modern retreat offers the peace of rural living with the sophistication you've been looking for.The main

    Jessie Bennett William Pitt Sothebys Intn'l

    74 Oak Ridge, Canaan, NY 12029
  • /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    2073 County Route 5, Canaan, NY 12029

    Welcome to Tilden Crossing House, a distinctive country home with old-world charm. Privately sited down a long, gravel, wildflower-lined drive on over seven acres of pastoral Columbia County landscape, the property offers a unique approach to architectural storytelling through its carefully selected vintage elements.The 3,350-square-foot center-hall residence captures the essence of

    Anthony D'Argenzio Houlihan Lawrence, Inc

    2073 County Route 5, 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
  • /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
  • /46

    $975,000

    • 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 Greater NY LLC

    18 Old Queechy Rd, Canaan, NY 12029
  • /53

    $1,300,000

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

    91 & 95 Miller Rd, Canaan, NY 12029

    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 with modern luxury. The

    Jessie Bennett William Pitt Sothebys Intn'l

    91 & 95 Miller Rd, Canaan, NY 12029
  • /42

    $855,000

    • 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
  • /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
  • /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
  • /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, 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

    $290,000

    • 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
  • /25

    $765,000

    • 5 Beds
    • 4 Baths
    • 3,165 Sq Ft

    53 Whitings Pond Rd, Canaan, NY 12029

    Step back in time in this sprawling, light filled, spacious gem. Huge front porch to sit in the shade of mature trees and perennials. Center hall branches off into large mostly original rooms with wide plank flooring, high ceilings, original period moldings and built in's. Large main bedroom on the first floor with walk in closet and bath. Country kitchen looking out over the special sun

    Leonard Brown Berkshire Hathaway HomeService

    53 Whitings Pond 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
  • /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
  • /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
  • /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

    $745,000

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

    263 Old Hudson Turnpike, Canaan, NY 12029

    PRICE CUT! All new eyebrow colonial transformed in to a modern efficient home with 3 bedrooms and 2 full baths. New Anderson windows, doors, roof, 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 system.New wrap around deck to enjoy your

    Sharon McArdle Berkshire Hathaway Home Services Blake

    263 Old Hudson Turnpike, Canaan, NY 12029
  • /55

    $589,000

    • 5 Beds
    • 3 Baths
    • 3,180 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. Brand new furnishings included: ready to go!! Be Sure to Check Out Virtual Media Tour. 3rd floor recently finished with new bath. Other floors recently renovated. Organized to

    David Birch Barns & Farms Realty

    105 McNamee Rd, Canaan, NY 12029
  • /46

    $824,999

    • 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
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