1. Connecticut
  2. Ashford
  3. 90-94 & 93 Upton Road
$1,700,000

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

  • 7 beds |
  • 5 baths |
  • 4,283 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in ——
  • Property Lot Size Icon291.6acre lot
  • Property Parking Icon 2 car garage
  • Property Price Per Square Feet Icon $397/sqft
  • Property List Date Icon Listed 5 days ago

Property 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 Status:
Active
Date Added:
August 4, 2025 at 11:41PM
Listing Office:
CR Premier Properties : (860) 315-9070
Listing Agent:
Nicole Gleason : (860) 792-1005
MLS ID:
24115774
  • Appliances: Electric CooktopWall OvenRefrigeratorDishwasher
  • Laundry: Lower Level
  • Basement: FullInterior AccessDirt FloorConcrete FloorFull With Walk-Out
  • A/C: Window Unit
  • Heating: BaseboardElectricOil
  • Fireplace: Fireplaces: 7

This listing courtesy of Nicole Gleason, CR Premier Properties

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Get Prequalified »
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location

Schools Nearby

E

E. O. Smith High School

1235 Storrs Rd, Storrs Mansfield, CT, 06268

Grades 9-12

7.19 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.