90-94 & 93 Upton Road, Ashford, CT 06278

Welcome to one of the most extraordinary and locally adored estates in Eastern Connecticut-nearly 300 acres of rolling fields, woodlands, and historic charm offered as a single, unmatched property. Privately set along a quiet, town-maintained dirt road, this expansive estate combines 93 and 90-94 Upton Road into a rare opportunity for legacy ownership. The centerpiece is a breathtaking 18th-century Cape, beautifully preserved and thoughtfully updated with modern systems and appliances, five fireplaces, a high-functioning, well-kept basement, and a detached two-car garage. From the stone walls, and the historic foundations to the vibrant gardens, the mature trees to the beautiful Knowlton and Moritz Brooks, every inch of this property exudes timeless New England charm. An athletic court and in-ground pool only add to the experience. Surrounded by vast, nearly untouched forest and with access to the Nipmuck Trail at the rear, this property also features miles of private, well-maintained trails-perfect for equestrians, nature lovers, and outdoor enthusiasts alike. Two additional saltbox-style homes offer potential for restoration or auxiliary use. Ideal for horseback riding, farming, a private vineyard or brewery, or simply your own secluded haven-this is a once-in-a-generation opportunity. This unique property includes three residences: a main home located at 93 Upton Rd. and two smaller homes situated at 90-94 Upton Rd. The main residence, built in 1733, offers 5 bedrooms and 3 full bathrooms. Each of the smaller homes, both built in 1900, features 1 bedroom and 1 bathroom. The parcel at 90-94 Upton Rd. covers approximately 95.8 acres, while the main parcel at 93 Upton Rd. spans about 195.8 acres. The below-grade square footage is approximately 1,766 sq. ft. for 93 Upton Rd. and 230 sq. ft. for 90 Upton Rd.