$1,695,000
COMING SOON

93 & 90-94 Upton Rd Ashford, CT 06278

Estimated payment $10,484/month

7 Beds
5 Baths
4,283 Sq Ft
291.6 Acres Lot

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: ComingSoon
  • 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

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Source: SmartMLS

MLS Number: 24167939

SmartMLS
Connecticut Windham County Ashford 06278

93 & 90-94 Upton Rd, Ashford, CT

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Kiara Rusconi
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Kiara Rusconi
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William Raveis Real Estate
(860) 329-4153
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