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

GRAND LEGACY ESTATE ON 291.6 ACRES w/REMODELED HISTORIC PRIMARY RESIDENCE & 2 ACCESSORY DWELLINGS! Gracefully spanning 2 contiguous parcels, this exceptional Eastern CT sanctuary embodies a rare convergence of early American heritage, refined country living, & remarkable land stewardship. Discreetly set along a quiet, town-maintained road, 93 & 90-94 Upton Road unfolds as a singular offering of scale & substance - well-suited for legacy ownership, multigenerational living, or the creation of a private rural compound of distinction. The centerpiece of the property is a 3,036sqft Cape residence dating to 1733, set on an expansive 198.8-acre parcel. Rich in history yet thoughtfully updated, the home showcases original wide-plank floors, 5 fireplaces, & preserved period details, complemented by seamless additions & modern systems for today's comfort. The welcoming foyer leads to a front-facing living room w/fireplace & a formal dining room featuring paneled walls, fireplace, & direct access to a wraparound deck-ideal for entertaining. A warm & inviting family room includes a traditional Dutch oven fireplace, custom built-ins, & multiple access points to the outdoors, creating effortless indoor-outdoor flow. The fully renovated 2024 kitchen offers solid surface countertops, custom wood cabinetry, LVP flooring, & all new appliances along w/a pantry & spacious eat-in dining area. ***CONTINUED*** The main level includes a private office with built-ins, separate entrance, and adjacent full bath-ideal for remote work or flexible use. A first floor primary bedroom features hardwood floors, double closets, & direct deck access w/scenic views. 2 additional bedrooms & a full bath complete the main level. Upstairs, 2 generously sized bedrooms w/fireplaces & wide-plank floors share an ensuite bath & enjoy ample storage. A large walk-in attic offers endless expansion potential. The lower level is pristine & functional w/updated mechanicals (2016), 200-amp electrical service, laundry area, & walkout access. The detached 2-car garage provides security & convenience for vehicles & recreational transportation & equipment accessories. A separate 95.8-acre parcel includes 2 unique accessory structures: a converted corn crib residence w/exposed beams, fireplace, kitchen, full bath, & vaulted bedroom; & a historic blacksmith shop w/vaulted ceilings, gas stove fireplace, loft, & roughed-in kitchen & bath-a compelling canvas for restoration or customization. The land itself is a defining feature - an expansive tapestry of open meadows, rolling clearings, antique stonework, & mature forest. The gentle presence of the Knowlton and Moritz Brooks, accompanied by natural waterfalls, lends both beauty & tranquility to the landscape. It is believed that native brook trout can still be found quietly finning throughout these aquatic networks. Recreational amenities include an athletic court & in-ground pool, while miles of private, well-maintained trails weave throughout the property. The surrounding woodlands remain largely untouched & provide direct access to the Nipmuck Trail, offering an immersive outdoor experience for equestrians, hikers, & nature enthusiasts alike. Whether envisioned as a private country estate, equestrian haven, family compound, or retreat rooted in nature & history, this quintessential New England property presents a truly rare opportunity.