$1,849,000
3 Bed • 3 Bath • 3,681 Sq. Ft.
215 Smith Road
Poughkeepsie, NY 12603
Listed with KW MidHudson
$2,300,000
Est. $13,111/moAmenia, NY 12501 · Dutchess County
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Step into a turn key investment with 9 years of profitable short term rental history and a business backed by a long standing, proven financing track record! This exceptional 1790 Georgian style estate comes with three standalone cottages, all fully renovated and operating as highly sought after vacation rentals. With commercial zoning already in place, this property blends historic charm, modern luxury, and serious income potential, while also offering a rare opportunity for future conversion into a boutique hotel or resort. Guests flock to this private country escape for its elegant main residence featuring wide plank hardwood floors, high ceilings, a library, music room, billiard room, and wine cellar, and return for the tranquility of the manicured grounds complete with a heated pool, putting green, walking trails, and a serene pond. Currently fully booked, this estate generates significant revenue even after accounting for full service cleaning and lawn maintenance. Whether you choose to live in the main home and rent out the three cottages, lease all four residences, or explore a larger scale hospitality concept, this is a rare chance to own a high performing asset with built in lifestyle benefits. Minutes from local hiking, dining, and the Berkshires, this is your chance to own a legacy property and a cash flowing business in one.
As reported by the listing office; verify enrollment with the district.
Listed with Keller Williams Realty Partner · Dominick DiFilippo · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 6:08 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
5
Sep 2026
Average Price
Active listings
$1,768,461
Sep 2026
Average Days on Market
Active listings
270 days
Sep 2026
Computed from 28 active OneKey MLS listings in Amenia, NY.
$1,849,000
3 Bed • 3 Bath • 3,681 Sq. Ft.
215 Smith Road
Poughkeepsie, NY 12603
Listed with KW MidHudson
$2,800,000
3 Bed • 3.5 Bath • 3,280 Sq. Ft.
15 Ferris
Red Hook, NY 12571
Listed with Rouse + Co Real Estate LLC
$1,895,000
4 Bed • 3.5 Bath • 3,200 Sq. Ft.
8 Sarah Court
Rhinebeck, NY 12572
Listed with Upstate Down