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For Sale

32 Old Route 199

Red Hook, NY 12571

$849K
6 BD · 6 BA · 3,500 sf · 4 ac · Built 1976
The residence

Tucked away at the end of a long, private driveway, yet just a short stroll to the village, Shepard's Knoll offers a rare and compelling combination of seclusion, character, and versatility. Set on four picturesque acres framed by mature trees and vibrant gardens, this distinctive property invites you to enjoy both peaceful retreat and everyday convenience. Originally conceived as a single-family residence, the home has been thoughtfully converted into two spacious units, separated by just one wall, making it simple to return to a grand single-family estate if desired. This flexibility opens the door to a range of possibilities, from multi-generational living to a smart investment opportunity. Unit one features four bedrooms and three bathrooms, along with a finished basement that expands the living space, currently generating steady long-term rental income. Unit two offers two bedrooms and two bathrooms and has a proven track record as a successful Airbnb. Both residences are filled with warmth and charm, each enhanced by a wood-burning fireplace and an additional wood stove, creating an inviting atmosphere. Step outside and the appeal continues. Expansive decks and porches provide the perfect setting for relaxing, entertaining, or simply taking in the serene pastoral views. The grounds are equally impressive, offering a collection of outbuildings that add both function and charm: a quaint cottage ideal for an artist's studio or fitness space, a former sheep barn with abundant storage, chicken coops, and a dedicated area once used for organic vegetable gardening. Whether you envision a private country sanctuary, an income-producing investment, or a flexible living arrangement that evolves with your needs, Shepherd's Knoll delivers on every level. With its proven versatility, natural beauty, and prime location, this is more than a property; it's an opportunity to create the lifestyle you've been looking for.

At a glance
Property type
Status
Active
Year built
1976
Lot size
4 acres
Living area
3,500 sf
MLS#
11715926
Beds · Baths
6 · 6
Location

Red Hook, NY.

Red Hook sits within Hudson Valley, in New York, and keeps the character of that stretch of the map — its streets, shoreline and architecture read as of a piece with the towns around it. Our advisors know the market here street by street and can speak to how a particular address sits within it.

Estimated Monthly Payment+
$4K/mo
Approximate · principal & interest only
Display Currency
$849K

Indicative conversion — settlement always in USD.

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Listing courtesy of JFIVE HOMES REALTY LLC · NYSMLS

My State MLS / New York State MLS.Listing data is provided by My State MLS / New York State MLS for the personal, non-commercial use of consumers, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Information is deemed reliable but is not guaranteed accurate and should be independently verified.

Listings updated Aug 20, 2026

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