Canaan, New York listings for sale

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$1,700,000 - Canaan, NY
126 Shaker Ridge Drive Canaan, NY - 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 stone fireplace, library and formal dining room, hardwood floors throughout, new roof, and geothermal heat + oil backup. Possibility of 1st floor Master. Guest Residence has workshop, 3 garage garage, endless pool and 2700sf 4BR3B living space. Also separate outdoor pool, indoor swim spa, outdoor jacuzzi, hot tub, zipline,& treehouse & access to community tennis & waste dropoff. Ideal for family compound, entertaining, work/residence. Ideal multigenerational family compound in the Berkshires.
1986 | 7 | 6 | 7,316 sqft.
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$1,600,000 - Canaan, NY
126 Shaker Ridge Canaan, NY - Berkshire/New York Contemporary Estate CHECK OUT VIRTUAL TOURS # 1, & #2. 6005 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 stone fireplace, library and formal dining room, hardwood floors throughout, new roof, and geothermal heat + oil backup. Possibility of 1st floor Master. Guest Residence has workshop, 3 garage garage, endless pool and 2700sf 4BR3B living space. Also separate outdoor pool, indoor swim spa, outdoor jacuzzi, hot tub, zipline,& treehouse & access to community tennis & waste dropoff.
1986 | 7 | 6 | 7,316 sqft.
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$1,299,000 - Canaan, NY
169 Cunningham Hill Road Canaan, NY - Experience the enchantment of this idyllic retreat! Nestled on a sprawling 36.95 acres, this stunning three-bedroom, two-bath contemporary farmhouse offers a serene escape from the hustle and bustle of everyday life. Accessed via a picturesque stone wall-lined driveway, off a quiet country dirt road, this property is a nature lover's paradise.Immerse yourself in the beauty of spectacular gardens, expansive open meadows, and lush mature woods with winding trails. Enjoy the tranquility of a gentle stream and three ponds that enhance the landscape. The impressive amenities include an oversized two-car garage with a loft, a three-stall horse barn, and a charming chicken coop. Plus, a large, heated studio equipped with electricity awaits your creativity- it's ideal for a workspace or a perfect conversion into a guest house.Two tax map parcels ( 28.95 acres with house & all outbuildings and 8 acres with underground electric & a gorgeous view ). Build on smaller parcel in future or sell/ gift to a family member/ friend. Don't miss your opportunity to make this extraordinary property your own! A fantastic location nestled next to the Berkshire border, just 15 minutes to Chatham, Pittsfield & Lenox, 30 minutes to Hudson & Gt. Barrington and 2 hours & 25 minutes from NYC & 2 hours from Boston.Open Houses on Saturday May 10th & Sunday May 11th 2025 from 12 noon to 2:00 pm both days !!!
1987 | 3 | 2 | 2,142 sqft.
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$995,500 - Canaan, NY
192 Old Queechy Road Canaan, NY - Nestled on 8.6 private acres, surrounded by nature conservancy and historic preservation land, this architect-designed compound offers the perfect blend of understated elegance and contemporary comfort. Located just minutes from Tanglewood, Jacob's Pillow, Kripalu, and world-class skiing in NY, MA, and Vermont, this serene escape is also within walking distance of one of the cleanest lakes in New York, with lake rights included.The main house, reminiscent of a European country house, in symphony with the surrounding landscape, is designed for both relaxation and entertaining, and features a double-height living room with a wood-burning stove, a formal dining room, an office/den, and a modern eat-in kitchen. Upstairs, three charming bedrooms and two full baths showcase architectural details, while a walkout basement offers additional potential living space.Adding to the appeal, the property includes a guest house with a full kitchen, wood-burning stove, bathroom with shower, and a spacious loft sleeping area - ideal for visitors or as an Airbnb rental. A separate studio provides the perfect space for a music room, yoga studio, workshop, or creative retreat.A paved circular driveway winds through wildlife-rich woodlands, open fields, and stunning rock outcroppings, with a babbling brook completing this peaceful setting. Everything has been done - just move in and enjoy!For the discerning buyer seeking a truly magical retreat in the heart of the Berkshires, this rare offering is an opportunity not to be missed.
2001 | 4 | 2 | 2,245 sqft.
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$935,000 - Canaan, NY
2205 County Route 5 Canaan, NY - 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, the home was thoughtfully customized to suit a relaxed yet refined lifestyle. With two spacious bedrooms, a cozy den that doubles as a convenient ground-floor guest bedroom, and three full bathrooms, the home strikes the perfect balance between form and function.From the moment you step inside, you'll be welcomed by a warm and inviting ambiance. The traditional dining room flows seamlessly into the living room, creating a cohesive space for intimate dinners or casual gatherings. An expansive great room offers the ideal setting for entertaining or enjoying quiet evenings by the fire, while abundant storage throughout ensures everything has its place.In 2005, a beautifully integrated addition elevated the home's livability with a bright, airy family room, a versatile bonus space perfect for a home gym or reading nook, and an inspiring artist's or craft studio that invites creativity to flourish. This thoughtfully designed expansion brings in even more light and dimension, making the home feel open and connected to its stunning natural surroundings.Step outside onto the mahogany deck and take in the tranquil views of your private pondan ideal backdrop for morning coffee, alfresco dinners, or stargazing from the comfort of your hot tub. The landscape is a peaceful blend of open meadows and lush woods, where deer, birds, and other wildlife are regular visitors.Throughout the home, large double-hung windows invite in natural light, creating an uplifting environment year-round. Whether you're curling up with a book, hosting friends, or simply soaking in the serenity, every space feels like a retreat.Enjoy the best of both worldstotal privacy with easy access to the charm and culture of the Berkshires. Just minutes from New Lebanon, West Stockbridge, Chatham, Williamstown, Pittsfield, and Lenox, and an easy drive to Albany (40 mins.), NYC (2.5 hrs.), and Boston (3 hrs.), this is country living without compromise.This is more than a homeit's a lifestyle, where peace, creativity, and convenience come together in perfect harmony.
1995 | 3 | 2 | 3,204 sqft.
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$749,900 - Canaan, NY
263 Old Hudson Turnpike Canaan, NY - Step into this brand 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 backyard. Spray foam sealed insulated full basement for warmth and dryness. Bright and airy rooms with windows galore. Lots of yard and a view of the mountains. Beautiful paved driveway and access to Queechy Lake, top 5 cleanest lakes in the state. Move in and live maintenance free for years. All new. Surrounded by a land conservatory on three sides. Close to TSP, I 90, Hudson, Chatham, Albany.
1984 | 3 | 2 | 1,404 sqft.
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$749,900 - Canaan, NY
263 Old Hudson Turnpike Turnpike Canaan, NY - Step into this brand 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 backyard. Spray foam sealed insulated full basement for warmth and dryness. Bright and airy rooms with windows galore. Lots of yard and a view of the mountains. Beautiful paved driveway and access to Queechy Lake, Top 5 cleanest lakes in the state. Move in and live maintenance free for years. All new. Surrounded by a land conservatory on three sides. Close to TSP, NYS thruway, Hudson, Chatham.
1984 | 3 | 2 | 1,404 sqft.
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$649,000 - Canaan, NY
105 Mcnamee Canaan, NY - 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 allow for private access to 2nd & 3rd floors. Massive Stone Fireplace from 1st floor through 2nd & 3rd floors.
1998 | 5 | 3 | 3,180 sqft.
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$599,000 - Canaan, NY
105 Mcnamee Canaan, NY - 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 allow for private access to 2nd & 3rd floors. Massive Stone Fireplace from 1st floor through 2nd & 3rd floors.
1998 | 5 | 3 | 3,180 sqft.
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$300,000 - Canaan, NY
28 Upper Queechy Road Canaan, NY - 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 a cozy office.The finished basement adds even more living space with a laundry center, tool shop, and bonus room. Enjoy the outdoors on one of two decks, surrounded by mature perennial gardens, a soothing waterfall, and a fire pit. This home is move-in ready and just waiting for you!10 minutes from Chatham Village and New Lebanon, 25 minutes from Pittsfield and all that the Berkshires offer!
1900 | 2 | 1 | 1,100 sqft.