Real Estate Agent in Connecticut and Western Massachusetts

90-94 & 93 Upton Road
Ashford, Connecticut

Single Family For Sale

7

Bedrooms

5 (full) / 0 (half)

Bathrooms

4,283

Sq Ft

$ 1,700,000

Price

90-94 & 93 Upton Road
Ashford, Connecticut

Ashford, Connecticut

Description:

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

Meet Our Team

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:

Alison Malkin
Alison Malkin

Broker/Owner

860-214-8008

Email
Alison Malkin
Nicole Malkin James

Broker/Owner

843-614-7222

Email
Alison Malkin
Luis Torres

Associate Broker

860-383-5211

Email
Alison Malkin
Debra Pliego

Realtor®

860-919-7376

Email
Alison Malkin
Madison Wells

Realtor®

860-538-7567

Email
Alison Malkin
Lori Sierpinski

Realtor®

860-222-4692

Email
Alison Malkin
Jim Murkette

Realtor®

860-539-5009

Email
Alison Malkin
Leah Pliego

Realtor®

860-681-7373

Email
Alison Malkin
Shaissa Acosta

Realtor®

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


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