Spend the summer surrounded by sweeping views of the Berkshires and Stissing Mountain at this custom-built retreat, privately set on three beautifully landscaped acres in Milan. Designed for relaxed indoor-outdoor living, the home's spacious open floor plan features soaring double-height ceilings, a dramatic two-story stone fireplace, a beautiful kitchen, and multiple dining and gathering areas. Walls of windows frame the mountain views, while an expansive deck provides the perfect spot for morning coffee, outdoor meals, or long summer evenings. The main level includes a private primary suite with ensuite bath, along with a powder room and laundry room. Upstairs are two additional bedrooms and a full bath. The fully finished lower level offers wonderful flexibility for guests or extended stays, with high ceilings, radiant-heated concrete floors, two additional rooms, a full bath, efficiency kitchen, and family room opening directly onto a bluestone patio. Outside is where summer really shines: enjoy the heated in-ground pool, expansive lawns, mountain views, and plenty of room to relax and entertain. The sunsets are something else! An approximately 800-square-foot finished outbuilding offers even more space on two levels, including a recreation room, gym, and second-floor deck. A detached two-car garage completes the property. Tucked away on a private road yet within easy reach of Rhinebeck and the best of the Hudson Valley, this is an idyllic home base for a summer in the country.

Property Details of 21 Contentment Lane

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of November 10, 2026 11:36 AM EST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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