A Rare Multi-Residence Opportunity on 11.75 Acres in Bloomingburg! Welcome to 853 Winterton Road — a truly exceptional 11.75-acre estate in the Pine Bush School District that offers both space and potential, tucked away in a serene farm-like setting yet convenient to all that the Hudson Valley has to offer. Drive up the long, paved circular driveway and take in the peaceful, private landscape lined with mature trees, open lawn, and a beautiful pond — the perfect blend of tranquility and usability. Main Residence: This spacious 3-bedroom, 2-bath Ranch-style home boasts over 2,100 square feet of classic charm and functionality. Inside, you'll find original hardwood floors, vintage touches, and a warm, welcoming living room with a cozy pellet stove. The bright eat-in kitchen and separate dining room are ideal for gatherings. Downstairs, the full, partially finished basement includes a second wood-burning stove, large windows, and a versatile workshop/laundry area with walk-out access. Second Dwelling – The Guest House: Nestled nearby is a charming 880 sq ft, 2-bedroom, 1-bath bungalow. While it’s ready for some TLC, it offers great character and potential — perfect as a guest house, rental opportunity, or extended family retreat. The Property: Enjoy nearly 12 acres of open and wooded land with a mix of level lawn, towering trees, and scenic pond views. Outbuildings and sheds offer space for storage or hobby use. Whether you’re dreaming of a mini-homestead, family compound, or income-generating property, this one checks every box. Location Perks: Situated just on the border of Orange County, this property gives you the best of both worlds — peace and privacy with quick access to major highways for an easy commute to NYC. Plus, you're in the heart of the Hudson Valley's most desirable offerings: wineries, trails, farmer’s markets, and charming towns. Don’t miss your chance to own this one-of-a-kind estate — full of history, opportunity, and natural beauty.