90-94 Upton Rd

Ashford, CT 06278

$1,700,000
Price
7
Beds
4,283 Sq. Ft.
$397 / Sq. Ft.
4,283
Sq. Ft.
$397
per Sq. Ft.
a view of a swimming pool
an aerial view of residential houses with yard
an aerial view of a house with swimming pool
a view of a houses and a yard
a house view with a garden space
a house view with swimming pool in front of it
front view of a house with a yard
a view of a house with a swimming pool
a house that has a big yard
a living room with furniture and a large window
a living room with furniture and a fireplace
a view of an entryway with workspace
a living room with furniture and a fireplace
a view of a dining room with furniture and wooden floor
a bedroom with a bed and a table in it
a spacious bedroom with a bed a couch and a couch
a bathroom with a granite countertop sink a mirror and a shower
a bedroom with a bed and a window
a living room with furniture and a window
a large white kitchen with cabinets
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a kitchen with granite countertop a sink a stove and cabinets
a view of room with window and wooden floor
a view of a door and chair
a view of a livingroom with furniture and a fireplace
a bathroom with a bathtub sink and mirror
a living room with furniture and a fireplace
a backyard of a house with plants and trees
an empty room with furniture and a fireplace
a view of an empty room with wooden floor and a window
a view of a house with backyard and sitting area
a view of an empty room
a view of a storage & utility room
a view of empty room with an empty room
a view of storage and utility room
a view of a house with backyard

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,...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.
  1. Listed by Nicole Gleason • CR Premier Properties
    P: (860)-792-1005 C: (860)-792-1005 nicole@crpremier.com
  2. Listed by Carol L Ryniewicz • CR Premier Properties
    P: (860)-315-9070 C: (860)-942-9293 carol@crpremier.com

Property Details for 90-94 Upton Road

Basement Description
Full, Interior Access, Dirt Floor, Concrete Floor, Full With Walk-Out
Direct Waterfront
Yes
Garages Number
2
Neighborhood
N/A
Style
Cape Cod, Saltbox
Garage Parking Info
Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 11/13/2025 09:00 AM

Property Details for 90-94 Upton Road

StatusActive
MLS #24119131
Days on Market145
Taxes$15,691 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1733
Lot Size291.60 AC / 12,702,096 SF
CountyWindham County

Location

Listing Courtesy of CR Premier Properties, Nicole Gleason; CR Premier Properties, Carol L Ryniewicz
Add your commute

Building Information for 90-94 Upton Road

Stories-Year Built1733Building Size-Lot Size291.60 AC / 12,702,096 SF

Payment Calculator

$9,593 per month

30 year fixed, 6.15% Interest

Principal and Interest

$8,286

Property Taxes

$1,308

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 90-94 Upton Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 44 to Upton Rd - Some directions say Elliot Rd
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.855714
  • Longitude: -72.200161
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $15,691
Interior and Exterior Features
Exterior Features
  • Exterior Features: Wrap Around Deck, Garden Area, Guest House, Stone Wall
  • Pool Description: Safety Fence, In Ground Pool
  • Waterfront Description: Brook, Access
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Refrigerator, Dishwasher
  • Attic Description: Crawl Space, Walk-In
  • Cooling System: Window Unit
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 7
  • Laundry Room Info: Lower Level
  • Rooms Total: 16
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Bedroom
Room 5
  • Listing Key: 3C41C68BB1E35669E0631A01100AE889
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 3C41C68BB1E35669E0631A01100AE889
  • Room Entry Order: 9
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete, Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1733
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: Combining 3 homes sq. ft. Main home 3036 sq. ft. 2nd house is 730 sq. ft. & 3rd home is 517 sq.ft.
  • Sq Ft Est Heated Below Grade: 0
Lot Information
  • Lot Description: Secluded, Treed, Cleared, Professionally Landscaped, Water View
  • Parcel Number: 999999999
  • Sq Ft Est Heated Above Grade: 4283.0
  • Sq Ft Total: 4283.0
  • Zoning: RA
Utilities
  • Heat Fuel Type: Electric, Oil
  • Hot Water Description: Electric, Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Public Records for 90-94 Upton Road

Taxable ValueLand$79,520Additions$57,680Total$137,200
Tax Record2024$4,714 ($393 / month)
Home Facts
Beds0Lot Size4,173,048 SqFtStyleMiscellaneous ResidentialZoningRACountyWINDHAMAPNASHF M:38 B:B L:1

Schools near 90-94 Upton Road

This home is within Regional School District 19.
Rating
School
Type
Grades
Distance
Ashford School
Public - PK to 8
E. O. Smith High School
Public - 9 to 12
Rating
School
Distance
Ashford School
PublicPK to 8

E. O. Smith High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 90-94 Upton Road, Ashford, CT 06278

90-94 Upton Road is a single family home for sale in Ashford, CT 06278. This property was listed for sale on August 14, 2025 by CR Premier Properties, it's currently listed at $1,700,000. This listing's school districts are Ashford School District, Regional School District 19. Nearby schools include Ashford School and E. O. Smith High School. 90-94 Upton Road is a 7-bed, 5-bath, 4,283 sqft single family home built in 1733.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of CR Premier Properties, Nicole Gleason; CR Premier Properties, Carol L Ryniewicz

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.