This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds, two storage sheds for garden tools and recreational items, and ample off-street parking. The main house offers 4 spacious bedrooms and 3 full baths, a large sunlit living room, a formal dining room, original hardwood floors, a grand staircase with the original banister, and a finished attic—perfect for a playroom, studio, or home office. The renovated kitchen features granite countertops, stainless steel appliances, an oversized island, tile flooring, and an electric fireplace, with a separate laundry room and an additional full bath located on the main level. The private second unit (or guest wing) is a legal 3 BR/2 Bth apartment and includes a first-floor primary bedroom with a walk-in shower, an open-concept living and dining area with beautiful views, two more bedrooms and a full bath upstairs, plus convenient second-floor laundry. Both units share a heated enclosed porch/mudroom for entry, while the main house also enjoys a formal front entrance with vintage appeal. Currently tenant-occupied on month to month contracts. Please contact the broker for rent roll, expenses, and additional details. A new 2000 gallon septic system was installed in 2021. Heating is provided by oil with central air in Unit 1, and mini-split systems were added to Unit 2 in 2023 for efficient year-round climate control. This is a truly unique Hudson Valley opportunity, perfectly positioned on the Ancram border and just two hours to Manhattan by car, or 20 minutes to Hudson for Amtrak access. There's so much to love! Come see for yourself!