Where historic charm meets retro-chic flair. This extraordinary 8,000+ SF estate seamlessly blends a meticulously preserved 1810 Federal manor with a whimsical 70s-style wing, creating an entertainer's paradise. Whether envisioned as a family compound, luxury inn, or serene retreat, the possibilities are endless, all set on a breathtaking 10-acre gentleman's farm with open lawn, mature trees, pond, indoor and outdoor pools, wonderful pool house and greenhouse/sunroom breakfast area, plus multiple potential building sites on an additional 147 acres available! Host unforgettable gatherings in the Modern wing's sunken living room, featuring a striking gold fireplace, before stepping up to the indoor pool and lounge, then onto the conservatory deck for cocktails. A free-standing Corning glass-block staircase leads to the sprawling 1,500 SF primary suite with a spa-like bath, dual sinks, and two dressing rooms. On the main level, the vibrant open kitchen boasting exposed beams, frosted glass counters, and sycamore cabinetry flows into the dining area and wet bar. A stunning rear breezeway, lined with exposed beams and floor-to-ceiling windows, connects to the cozy media room and the historic Federal wing, where four ensuite bedrooms offer inviting guest accommodations. Outside, a blue stone terrace leads to the pool and pool house with a wood-burning fireplace ready to transform into an apartment, office, or party barn. A 5-bay garage awaits car enthusiasts. Additional parcels of land, 96 acres and 48 acres, offers agricultural potential, currently hosting Black Angus pastures and a thriving black currant crop. Nearby, the world-renowned Omega Institute in Rhinebeck provides meditation retreats and farm-to-table dining, while Bard College's Frank Gehry-designed Fisher Center offers world-class culture all just two hours from Manhattan. Additional land available! See MLS Land Listings on Rowe Rd (96 acres) and Route 199 (48 acres). Bring your architect and transform Red Hook Farmstead into your dream estate!