$1,695,000
PENDING

93 & 90-94 Upton Rd Ashford, CT 06278

Estimated payment $10,466/month

Total Views 1,822
7 Beds
5 Baths
4,283 Sq Ft
$396 Price per Sq Ft

Highlights

  • Guest House
  • In Ground Pool
  • 291.6 Acre Lot
  • E.O. Smith High School Rated A-
  • Waterfront
  • Cape Cod Architecture

About This Home

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***

Listing Agent

Kiara Rusconi

William Raveis Real Estate Brokerage Phone: (860) 573-3382 License #RES.0813155 Listed on: 05/27/2026

William Raveis Real Estate

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $15,733

Year Built

  • Built in 1733

Lot Details

  • 291.6 Acre Lot
  • Waterfront
  • Stone Wall
  • Garden
  • Property is zoned RA

Parking

  • 2 Car Garage

Home Design

  • Cape Cod Architecture
  • Saltbox Architecture
  • Concrete Foundation
  • Stone Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Clap Board Siding

Interior Spaces

  • 4,283 Sq Ft Home
  • 7 Fireplaces
  • Entrance Foyer
  • Workshop
  • Concrete Flooring
  • Storm Windows
  • Laundry on lower level

Kitchen

  • Built-In Oven
  • Electric Cooktop
  • Dishwasher

Bedrooms and Bathrooms

  • 7 Bedrooms
  • 5 Full Bathrooms

Attic

  • Attic Floors
  • Storage In Attic
  • Walk-In Attic
  • Unfinished Attic

Unfinished Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry
  • Dirt Floor
  • Basement Storage

Pool

  • In Ground Pool
  • Fence Around Pool

Outdoor Features

  • Wrap Around Balcony
  • Patio
  • Rain Gutters

Schools

  • Ashford Elementary School
  • Smith High School

Utilities

  • Window Unit Cooling System
  • Floor Furnace
  • Baseboard Heating
  • Hot Water Heating System
  • Heating System Uses Oil
  • Power Generator
  • Private Company Owned Well
  • Hot Water Circulator
  • Electric Water Heater
  • Fuel Tank Located in Basement
  • Cable TV Available

Additional Features

  • Guest House
  • Property is near golf course

Listing and Financial Details

  • Assessor Parcel Number 1669803

Home Details

Home Type

Single Family

Est. Annual Taxes

$15,733

Year Built

Built in 1733

Lot Details

291.6 Acres

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Cape Cod, Saltbox
  • Sq Ft Est Heated Above Grade: 4283
  • Total Sq Ft: 4283
  • Year Built: 1733
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Park, Public Rec Facilities, Stables/Riding
  • In Law Access: DETCH,ENTRY
  • Remarks Public Addendum: 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.
  • Direct Waterfront: Yes
  • Home Warranty Offered: No
  • Directions: GPS Friendly. Route 44 to Upton Road - Some directions may reference Elliot Road.
  • In Law Apartment: Yes
  • Street Type: Road
  • Office Attribution Contact: (860) 633-0111
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 7
  • Total Bathrooms: 5
  • Full Bathrooms: 5
  • Fireplaces: 7
  • Attic Description: Unfinished, Storage Space, Floored, Walk-In
  • Basement Description: Full, Unfinished, Storage, Interior Access, Dirt Floor, Concrete Floor, Full With Walk-Out
  • Interior Amenities: Cable - Available
  • Appliances: Electric Cooktop, Wall Oven, Refrigerator, Dishwasher
  • Additional Rooms: Foyer, Workshop
  • Laundry Room Info: Lower Level
  • Attic: Yes

Exterior Features

  • Exterior Features: Wrap Around Deck, Gutters, Garden Area, Guest House, Stone Wall, Patio
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete, Stone
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Brook Walk to Water View Access
  • Swimming Pool: Yes
  • Pool: Safety Fence, In Ground Pool
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 2
  • Garage And Parking: Detached Garage

Utilities

  • Cooling System: Window Unit
  • Heat Type: Baseboard, Hot Water
  • Heat Fuel Type: Electric, Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Electric, Domestic, 50 Gallon Tank
  • Water Source: Private Well
  • Sewer: Septic

Schools

  • Intermediate School: Per Board of Ed

Green Features

  • Energy Features: Generator Ready, Storm Windows

Lot Info

  • Acres: 291.6
  • Lot Description: Some Wetlands Treed Cleared Professionally Landscaped Rolling Water View
  • Flood Zone: No
  • Zoning: RA
  • Parcel #: 1669803

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 15733

MLS Schools

  • Elementary School: Ashford
  • Middle Jr High School: Per Board of Ed
  • High School: Smith

Map

Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
06/08/2026 06/08/26 Pending -- -- --
06/03/2026 06/03/26 For Sale $1,695,000 -- $396 / Sq Ft
Source: SmartMLS

Source: SmartMLS

MLS Number: 24167939

SmartMLS
Connecticut Windham County Ashford 06278

93 & 90-94 Upton Rd, Ashford, CT

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

SmartMLS IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Nearby Homes
Kiara Rusconi
Listing Agent
Kiara Rusconi
Section Image
William Raveis Real Estate
(860) 329-4153
Your Personal Tour Guide

Ask me questions while you tour the home.