$1,625,000
4 Bed • 4 Bath • 3,200 Sq. Ft.
25 Willow Glen Road
Red Hook, NY 12571
Listed with Upstate Down
$1,695,000
Est. $9,865/moPine Plains, NY 12567 · Dutchess County
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Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and Millerton, and 20 minutes to Millbrook.
As reported by the listing office; verify enrollment with the district.
Listed with Compass Greater NY, LLC · Byron W. Anderson · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 18, 2026, 8:07 AM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
2
Sep 2026
Average Price
Active listings
$2,152,552
Sep 2026
Average Days on Market
Active listings
165 days
Sep 2026
Computed from 30 active OneKey MLS listings in Pine Plains, NY.
$1,625,000
4 Bed • 4 Bath • 3,200 Sq. Ft.
25 Willow Glen Road
Red Hook, NY 12571
Listed with Upstate Down
$1,500,000
4 Bed • 3.5 Bath • 3,034 Sq. Ft.
3244 Sharon Turnpike
Millbrook, NY 12545
Listed with Houlihan Lawrence Inc.
$1,575,000
5 Bed • 5 Bath • 5,698 Sq. Ft.
162 Crum Elbow Road
Hyde Park, NY 12538
Listed with Serhant LLC