32 Old Route 199
Red Hook, NY 12571
For Sale
Shepherd’s Knoll represents a rare opportunity to own a versatile multi-family estate at 32 Old Route 199, positioned perfectly between the seclusion of a 4-acre country retreat and the vibrant culture of the Village of Red Hook. This property is reached via a long private driveway that opens to reveal a meticulously maintained 3,500 square foot home framed by mature trees and vibrant gardens.
The residence is currently configured as a two-unit dwelling, providing an excellent foundation for an income-producing investment or multi-generational living. Unit One is the larger of the two, offering four spacious bedrooms and three bathrooms. It features a finished basement for additional recreational space and is currently a reliable source of long-term rental income. Unit Two consists of two bedrooms and two bathrooms and has established a successful track record as a high-demand short-term rental.
Both units exude warmth and character, highlighted by wood-burning fireplaces and additional wood stoves that create a cozy Hudson Valley atmosphere. The layout is thoughtfully designed so that the units are separated by only one wall, allowing for an effortless transition back into a 6-bedroom single-family residence if desired. Natural light floods the interiors through strategically placed skylights and large windows.
The exterior of the property is equally compelling, offering expansive decks and porches designed for taking in the serene pastoral views. The 4-acre lot is a gardener’s paradise, featuring a dedicated area for organic vegetable gardening and lush landscaping. Several outbuildings add immense value and functional potential, including a quaint cottage ideal for a fitness studio or creative workspace, and a large former sheep barn providing ample storage or workshop space.
Located in the heart of Dutchess County, this property offers the ultimate Red Hook lifestyle. Whether you are looking for a sustainable homestead with chicken coops and acreage or a savvy real estate investment with proven cash flow, Shepherd’s Knoll delivers on every level. Its proximity to local amenities while maintaining privacy makes it a standout offering in today’s market.
Red Hook is a historic and vibrant community in Northern Dutchess County, known for its rich agricultural heritage and cultural center. The area surrounding 32 Old Route 199 offers a unique blend of rural charm and modern convenience. Residents enjoy easy access to local farm stands, boutique shops, and a variety of dining options located within the Village of Red Hook.
Commuters and travelers benefit from the property’s central location. The Rhinecliff Amtrak station is just a short drive away, providing a scenic rail connection to New York City. Major roadways like the Taconic State Parkway and Route 9 are easily accessible, linking the area to the broader Hudson Valley and the Catskills. You can learn more about local infrastructure at the Town of Red Hook official website.
Outdoor enthusiasts will appreciate the proximity to several state parks and conservation areas. The nearby Poets’ Walk Park and Ferncliff Forest offer miles of hiking trails and breathtaking views of the Hudson River and Catskill Mountains. For those interested in local history and culture, the Vanderbilt Mansion National Historic Site is located just south in Hyde Park.
The neighborhood is also close to Bard College, which serves as a cultural hub for the region, offering world-class performances at the Fisher Center for the Performing Arts and a variety of public lectures and galleries. This proximity adds a unique intellectual and artistic energy to the local community.
Daily life in Red Hook is supported by excellent local amenities, including the Red Hook Public Library and numerous community-supported agriculture (CSA) programs. The area is renowned for its apple orchards and vineyards, which provide seasonal activities and fresh local produce year-round. Detailed information on local recreation can be found through the Dutchess County Parks Department.
This property is located at 32 Old Route 199, Red Hook, NY 12571