$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 2 months ago

Property Description

Shepherd's Knoll offers rare privacy and flexibility, which is less than two miles from the village. Set on four beautiful acres that include lawns, pastures, and lightly wooded areas, this distinctive property sits at the end of a long private drive. It includes two spacious living units that could easily be converted back to a single-family home. Unit One features four bedrooms, three bathrooms, and a finished lower level. Unit Two offers two bedrooms and two bathrooms with a strong history as a short term rental. Both spaces include wood burning fireplaces and a wood stove, creating a warm, inviting atmosphere. Outdoor living shines here. expansive decks and porches overlook pastoral views, while the grounds include a charming studio cottage, a former sheep barn with storage, chicken coops, and established garden areas, ideal for creative use, light homesteading, or quiet retreat. Located just minutes from Bard College, a campus that includes the Fisher Center, and Montgomery Place. The property blends country seclusion with access to Hudson Valley cultural life. Whether you need multi-generational flexibility, a home plus a guest setup, or a private sanctuary close to town, Shepherd's Knoll offers a lifestyle that's increasingly hard to find.

Listing Status:
Active
Date Added:
April 22, 2026
Data Last Updated:
June 26, 2026 at 9:38PM
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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