155 Paine Road Set on a breathtaking stretch of rolling countryside in historic Woodstock, this extraordinary Federal Colonial reproduction blends timeless New England craftsmanship with modern luxury across a remarkable multi-parcel estate. Approached by a long winding driveway, the home is perfectly positioned to capture sweeping pastoral views, overlooking fenced fields, hay meadows, and distant farmsteads. Designed with exceptional attention to detail, the residence features a handcrafted artisan kitchen with Wolf and Sub-Zero appliances, soapstone and marble countertops, cooling drawers, wine chillers, and sun-filled gathering spaces framed by French doors and endless views. The home offers five Rumford fireplaces, luxurious bedroom suites each with private baths, a stunning primary suite with reading nook, spa-inspired bath, custom wardrobes, and private deck overlooking the heated gunite pool, pool house, stone patio, and outdoor fireplace. A dramatic central staircase leads through all three finished levels, including a third-floor bonus retreat with full bath, while an elegant private in-law suite offers its own entrance, living area, fireplace, and full bath and the home is geothermal. Complementing the property is a remarkable reconstructed 1800s post-and-beam barn featuring eight stalls, lofts, hay and equipment storage, paddocks, turnouts, hydrants, and 200-amp electrical service-ideal for equestrian use, entertaining, events, hobby farming, endless country living at its finest Energy efficiency meets luxury living with a geothermal heating and cooling system, dedicated geothermal well, separate house and barn well, whole-house generator setup, and propane service supporting key systems throughout the property. Included in the offering are four parcels totaling over 21 acres, including two additional approved buildable lots, open space acreage, gardens, a skating pond. Additional Features Include: * Heated gunite in-ground pool with pool house * Two upper-level south-facing balconies with panoramic views * French doors throughout allowing abundant natural light * Open-concept design thoughtfully positioned for sunrise exposure * Extensive fenced pasture and turnout areas * Large garden space and private skating pond * Separate dedicated well for geothermal system efficiency * Generator-ready propane infrastructure * Finished third-floor bonus suite with private bath * Reconstructed antique post-and-beam barn relocated from a historic Woodstock farm * Potential for multigenerational living, equestrian use, hobby farm, or private retreat A rare opportunity to own an iconic Connecticut country estate where historic inspiration, luxury craftsmanship, and modern efficiency come together in one unforgettable setting.