358 Shelley Hill Road

Welcome to a rare and remarkable retreat on 129 acres comprised of meadows, woods, and miles of groomed walking trails. This breathtaking property features two large private ponds - one complete with dock - and a meticulously renovated 1940s stone carriage house offering nearly 3,000 square feet of refined modern living. The lower level of this 2-story home boasts a living room with sleeper sofa, wet bar, and wood-burning fireplace, a primary bedroom with office area, and a full bathroom. An open staircase leads to the upper level, where railroad rail beamed ceilings and a loft-style layout create a warm, inviting atmosphere. The second floor features a TV lounge with a large leather sectional and a second full bathroom, along with an additional living area showcasing another wood-burning fireplace and sleeper sofa. At the back of the open space lies a fully equipped chef’s kitchen, outfitted with a premium Wolf 6-burner stove, custom Sub-Zero refrigerator, and large windows offering views of the tranquil ponds. Step outdoors to enjoy a professionally landscaped Italian marble patio, complete with a wood-burning stone fireplace, dual propane torches, and ample space for alfresco dining and entertaining. For recreation and hosting, the 2022-built Sports Barn delivers an additional 3,200 square feet of space. It includes a basketball court, convertible pool/ping pong table, wireless sound system, 85-inch Smart TV, and expansive room for indoor entertaining year-round. Situated less than 20 minutes from Millbrook and Rhinebeck villages and the Taconic State Parkway. Two hours from New York City. This unique property has played host to numerous memorable events, including weddings (up to 200 guests maximum allowed), and was the backdrop for a film featured at the Woodstock Film Festival. Its charm and capacity make it an ideal setting for weddings, private events, and creative productions. Owner will provide portable bathrooms and dumpster for event rentals. Photos/videos from past events available upon request. Available for rent starting October 1, 2025 at $15,000 / month (one month minimum) or for events. Event fee is $20,000. Rentals require a $5,000 refundable security deposit and a $500 post-rental cleaning fee.