$899,000

32 Old Route 199, Red Hook, NY 12571

  • 6 beds |
  • 5 baths |
  • 3,500 sqft
  • Property Icon Duplex
  • Property Year Built Icon Built in 1976
  • Property Lot Size Icon4acre lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $257/sqft
  • Property List Date Icon Listed 21 days ago

Property Description

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, Shepard'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.

Listing Status:
Active
Date Added:
April 22, 2026
Data Last Updated:
May 11, 2026 at 7:39PM
Listing Office:
JFive Homes Realty,LLC : 845-758-6842
Listing Agent:
Jennifer Fivelsdal : 845-594-9947
MLS ID:
20261774
  • Appliances: Built-In Electric RangeDryerDishwasherElectric OvenWasher
  • Flooring: Combination
  • A/C: Window Unit(s)
  • Heating: ElectricForced AirOil
  • Fireplace: Fire PitLiving RoomFireplaceFireplaces: 2
  • Style: Ranch
  • General: Block1
  • Originating MLS: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS®)
  • School District: Red Hook Central School District
  • County: Dutchess
  • Zoning: RD3134889-6172-00-625810-000
  • Utilities: Cable AvailableElectricity Connected
  • Water: Well
  • Source: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS®)

This listing courtesy of Jennifer Fivelsdal , JFive Homes Realty,LLC

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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