Welcome to 11 Haggerty Hill Rd - a rare Hudson Valley equestrian estate set on over 26 private acres just 5 minutes from the Village of Rhinebeck and approximately 90 miles to the GW Bridge. One of Rhinebeck's earliest equestrian properties, this turnkey estate blends historic character with a complete modern transformation, offering refined country living in one of the Hudson Valley's most sought-after locations. The residence was fully rebuilt between 2017-2019 after being stripped to the studs. In 2025, the home was further enhanced with a dramatic 900 sq ft great room featuring 20-foot vaulted ceilings, exposed beams, two hunter ceiling fans, and a grand propane fireplace; along with a 220 sq ft artist studio addition with mini-split heating and cooling and a half bath off the great room, resulting in a thoughtfully redesigned 3-bedroom, 2.5-bath Colonial with 3,723 sq ft of finished living space. Natural light pours through 96 Andersen divided-light double-pane windows throughout the home. The chef's kitchen (2019) features custom cabinetry, cherry countertops, updated appliances, and flows seamlessly into the dining area with direct access to the rear deck for effortless indoor-outdoor living. Additional upgrades include central air, three-zone hydronic propane heating, drilled well & well pump (2015), concrete septic system (2019), bluestone walkways (2025), extensive landscaping (2025), and new covered front porch (2025). The equestrian facilities are fully equipped for immediate use and include a historic 50x120 steel-framed indoor riding arena with 22 plexiglass windows, observation room, limestone footing, lighting, ventilation fan, and 100-amp service. Additional improvements include a six-stall barn with tack room, feed room, hayloft, water, and electric, multiple paddocks, utility building, run-in sheds, and chicken coop. A rare offering combining luxury living, equestrian functionality, historic depth, and complete privacy in an exceptional Rhinebeck setting.