$625,000
4 Bed • 3.5 Bath • 3,349 Sq. Ft.
6 Fair Oaks Drive
Poughkeepsie, NY 12603
Listed with Absolute Real Estate of NY Inc
$639,000
Est. $4,285/moPawling, NY 12564 · Dutchess County
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Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.
As reported by the listing office; verify enrollment with the district.
Listed with Ellis Sotheby's Intl Realty · Leigh Tripathi · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 3:09 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
11
Sep 2026
Average Price
Active listings
$1,418,953
Sep 2026
Average Days on Market
Active listings
192 days
Sep 2026
Computed from 52 active OneKey MLS listings in Pawling, NY.
$625,000
4 Bed • 3.5 Bath • 3,349 Sq. Ft.
6 Fair Oaks Drive
Poughkeepsie, NY 12603
Listed with Absolute Real Estate of NY Inc
$550,000
3 Bed • 3 Bath • 2,014 Sq. Ft.
27 Bobolink Lane
Salt Point, NY 12578
Listed with eXp Realty
$475,000
3 Bed • 2 Bath • 1,220 Sq. Ft.
158 Stagecoach Pass
Stormville, NY 12582
Listed with Keller Williams Realty Partner