Bedrooms
Bathrooms
Sq Ft
Price
Ashford, Connecticut
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.
Listing Courtesy of CR Premier Properties
Our team consists of dedicated real estate professionals passionate about helping our clients achieve their goals. Every client receives personalized attention, expert guidance, and unparalleled service. Meet our team:
Broker/Owner
860-214-8008
EmailBroker/Owner
843-614-7222
EmailAssociate Broker
860-383-5211
EmailRealtor®
860-919-7376
EmailRealtor®
860-538-7567
EmailRealtor®
860-222-4692
EmailRealtor®
860-539-5009
EmailRealtor®
860-681-7373
EmailRealtor®
860-249-1641
Email
Acres : 291.6
Appliances Included : Electric Cooktop, Wall Oven, Refrigerator, Dishwasher
Attic : Crawl Space, Walk-In
Basement : Full, Interior Access, Dirt Floor, Concrete Floor, Full With Walk-Out
Full Baths : 5
Baths Total : 5
Beds Total : 7
City : Ashford
Cooling : Window Unit
County : Windham
Elementary School : Per Board of Ed
Fireplaces : 7
Foundation : Concrete, Stone
Fuel Tank Location : In Basement
Garage Parking : Detached Garage
Garage Slots : 2
Description : Secluded, Treed, Cleared, Professionally Landscaped, Water View
Neighborhood : N/A
Parcel : 999999999
Pool Description : Safety Fence, In Ground Pool
Postal Code : 06278
Roof : Asphalt Shingle
Sewage System : Septic
SgFt Description : Combining 3 homes sq. ft. Main home 3036 sq. ft. 2nd house is 730 sq. ft. & 3rd home is 517 sq.ft.
Total SqFt : 4283
Tax Year : July 2025-June 2026
Total Rooms : 16
Watersource : Private Well
weeb : RPR, IDX Sites, Realtor.com
Phone
860-384-7624
Address
20 Hopmeadow St, Unit 821, Weatogue, CT 06089