From the outside, 159/161 Chappaqua Road presents as a charming farmhouse—but it offers far more than its picturesque post-and-rail fence suggests. Set on 1.29 acres, with a newly renovated guest house Cottage, this 19th-century compound seamlessly blends historic character with modern luxury, featuring a four-bedroom, 3.1-bath Colonial-style Main House. A bluestone walkway leads to the stately entry hall of the main home, where approximately 3,000 square feet of living space highlights original antique flooring, exposed brick and beams, sawn wood paneling, marble fireplace, multiple porches and balconies, French doors, and classic built-ins. These timeless details are thoughtfully complemented by contemporary upgrades, including granite countertops, stainless steel appliances, marble baths, two-zone central air, a security system, hot tub and generator. The main residence includes a spacious primary suite, three additional bedrooms, a home office, and a fully renovated kitchen with a butler's pantry and mudroom. Recent enhancements feature an oversized sliding French door opening to a two-tiered stone porch complete with a luxury hot tub and firepit. The guest house Cottage offers exceptional versatility, with a living and dining area, full kitchen, powder room, a primary bedroom with a spa-like bath, and an additional ensuite bedroom with a separate sitting area—ideal for guests, extended family, or rental potential. Additional amenities include a detached garage and an oversized shed.