126 Shaker Ridge Drive, Canaan, NY 12029 (MLS # 20255629)

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor pools. Outdoor highlights include a hot tub, pool house with bathroom, pavilion, garden, and a fully enclosed treehouse for summer overnights, along with deeded Queechy Lake rights for swimming and kayaking. The main wing of the home features a dramatic triple-height great room with a fieldstone fireplace, flanked by a wraparound deck. The stunning southeast-facing views of the Taconic and Berkshire Hills turn every sunrise and sunset into a cherished ritual. A large kitchen is designed for the serious home cook, with Sub-Zero refrigerator, professional hood, and dual pantries. The breakfast bar opens directly to a cozy living space with its own fireplace, dining area, and mountain views. Custom built-ins for books and LPs encourage everyone to slow down and savor life's quiet moments. On the second level are three bedrooms, including a primary suite with fireplace, walk-in closet, and private balcony, plus a solarium and office nook. A breezeway connects to the north wing, where an indoor lap pool provides a year-round spa-like retreat. This section offers four additional bedrooms, three bathrooms, a kitchenette, loft-like studio, workshop, and attached three-car garage. Recent upgrades include a new geothermal heating system, refinished decks, new flooring throughout the main wing of the house, fresh exterior paint, and a new roof on all structures. The property sits on one of the largest lots in the sought-after community of Shaker Ridge, whose residents enjoy private tennis courts and a peaceful, well-maintained community setting. Minutes from Chatham, PS21 Arts Center, the Berkshires, and within easy reach of Hudson, Albany, western Massachusetts, and five ski resorts, this is a rare opportunity to own a one-of-a-kind Hudson Valley estate with total privacy, inspiring architecture, and unmatched versatility for entertaining or multigenerational living.

Last Updated	11/12/2025	Year Built	1986
Community	Canaan	Garage Spaces	3.0
County	Columbia

Additional Details

AIR	CENTRAL AIR, GEOTHERMAL, HEAT PUMP
AIR CONDITIONING	Yes
AMENITIES	Trash
APPLIANCES	DISHWASHER, DISPOSAL, DRYER, FREEZER, MICROWAVE, Oven, RANGE, RANGE HOOD, REFRIGERATOR, TRASH COMPACTOR, WASHER, Washer/Dryer, WATER SOFTENER
AREA	Canaan
BASEMENT	Crawl Space, PARTIAL, Yes
CONSTRUCTION	Frame, Wood Siding
EXTERIOR	Garden, Lighting, Outdoor Grill, Private Yard
FIREPLACE	Yes
GARAGE	Attached Garage, Yes
HEAT	BASEBOARD, GEOTHERMAL, Oil, Radiant Floor
HOA DUES	388
INTERIOR	Beamed Ceilings, Breakfast Bar, High Speed Internet, Open Floorplan, Pantry, Storage, Vaulted Ceiling(s), Walk-In Closet(s)
LOT	20.3 acre(s)
LOT DESCRIPTION	Gentle Sloping, LANDSCAPED, PRIVATE, SECLUDED, Sloped, Views, WOODED
LOT DIMENSIONS	20.3
PARKING	Driveway, Garage Faces Front, Off Street, Private, Attached, Garage
POOL DESCRIPTION	Heated, Indoor, In Ground
SEWER	Septic Tank
STYLE	Contemporary
TAXES	19021
UTILITIES	Electricity Connected
VIEW	Yes
VIEW DESCRIPTION	Forest, Hills, Mountain(s), Rural, Trees/Woods
WATER	Private, Well

Location

 

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