93 Upton Rd

Ashford, CT 06278

$1,695,000
Price
7
Beds
4,283 Sq. Ft.
$396 / Sq. Ft.
4,283
Sq. Ft.
$396
per Sq. Ft.
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UNRIVALED LEGACY ESTATE ON 291.6 ACRES!
Private sanctuary w/remodeled primary residence & 2 accessory dwellings.
Set along quiet, town maintained road unfolding as a singular offering of scale & substance.
Well-suited for legacy ownership, multigenerational living, or a private compound of distinction.
93 UPTON ROAD - Beautifully preserved, updated, & turnkey c.1733 principle Cape Cod home.
Front-to-back family room offers casual versatility w/direct connection to deck & additional door entry.
Authentic character is exuded through multiple fireplaces, rich timber flooring, & period detailing.
Expansive formal dining room w/elegant paneled walls & fireplace.
Natural light illuminates rooms through several sliding glass doors creating a natural flow for indoor/outdoor living & entertaining.
Front facing living room anchored by a classic fireplace & hardwood flooring.
Freshly painted neutral interiors throughout.
2024 renovated kitchen is a carefully curated blend of form & function.
Custom wood cabinetry, luxury vinyl plank flooring, tile backsplash, & solid surface countertops.
Full suite of newly installed appliances, double wall ovens, electric cooktop, refrigerator/freezer, vent hood, dishwasher, & sink.
Generous eat-in dining area & pantry compliment the highly functional culinary space.
Richly paneled front facing secondary entry & mudroom.
Dedicated office w/built-in bookcases, new flooring, full bathroom, & its own side entry door.
Ensuite full bathroom off office with vanity, loo, & shower.
Primary house enjoys 5 total bedrooms w/3 on main level. First floor Bedroom #1 (1st of 5 bedrooms in main house).
First floor Bedroom #2 (2nd of 5 bedrooms in main house). All bedrooms comfortably outfitted w/hardwood floors & closets.
Second main level full bathroom w/vanity, loo, & tub/shower.
Spacious main level primary bedroom w/hardwood floors, double closets, and lovely sitting area. First floor Bedroom #3 (3rd of 5 bedrooms in main house).
Primary bedroom serenely gazes out upon the vast back landscape with easy access to back deck through its own sliding glass door.
Incredible back deck w/access points from several first floor primary rooms. Virtually staged to show space for multiple seating areas.
The upper level is dedicated to slumber w/2 well-scaled bedrooms. Second floor Bedroom #1 (4th of 5 bedrooms in main house).
Upper level bedrooms are enhanced by wide-plank flooring, fireplaces, & ample storage. Second floor Bedroom #2 (5th of 5 bedrooms in main house).
Well appointed second floor Jack & Jill full bathroom servicing both upper bedrooms.
Substantial walk-in attic presents outstanding potential for expansion if preferred.
Many significant upgrades to utility including boiler, hot water heater, oil tank, & 200-amp electrical service - all replaced in 2016.
Recreational amenities include an athletic court & in-ground pool. Virtual pool rendering shows example for potential for existing pool & surrounding hardscape remodel.
Detached 2-car garage just steps from main house & sited on 93 Upton Road parcel.
Estate inclusive of 2 character-rich accessory dwellings nestled on separate 95.8 acre parcel (part of 291.6 total acres). Endless opportunity for family living, guest accommodations, workplace, gym, studio, rental income, or long-term investment.
90 UPTON ROAD - Former corn crib converted into charming residence.
90 Upton Road - Showcasing exposed beams, hardwood floors, built-in bookcases, fireplace, open living/dining layout, & main level kitchen.
90 Upton Road - Upper level reveals a vaulted bedroom w/charming architectural detail & a full bathroom.
94 UPTON ROAD - Historic blacksmith shop converted into accessory dwelling.
94 UPTON ROAD - Open main level offers a compelling canvas for restoration or customization, featuring soaring vaulted ceilings, exposed beams, gas stove fireplace, & roughed kitchen & bath.
94 UPTON ROAD - Spiral staircase leads to loft space.
The land is pure magic w/well-maintained trails, open meadows, rolling clearings, antique stone walls, untouched mature forest, natural waterfalls, gently babbling Knowlton & Moritz Brooks & direct access to Nipmuck Trail.
Quintessential New England setting presents a truly rare opportunity for a private country estate, equestrian haven, family compound, or retreat rooted in nature & history.

Description

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...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
  1. Listed by Kiara C Rusconi • William Raveis Real Estate
    P: (860)-573-3382 C: (860)-573-3382 kiararusconi@aol.com

Property Details for 93 Upton Road

Basement Description
Full, Unfinished, Storage, Interior Access, Dirt Floor, Concrete Floor, Full With Walk-Out
Direct Waterfront
Yes
Expected Active Date
06-03-2026
Garages Number
2
Neighborhood
N/A
Style
Cape Cod, Saltbox
Garage Parking Info
Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 06/03/2026 04:05 AM

Property Details for 93 Upton Road

StatusActive
MLS #24167939
Days on Market1
Taxes$15,733 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1733
Lot Size291.60 AC / 12,702,096 SF
CountyWindham County
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Location

Listing Courtesy of William Raveis Real Estate, Kiara C Rusconi
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Building Information for 93 Upton Road

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

Payment Calculator

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$9,757 per month

30 year fixed, 6.36% Interest

Principal and Interest

$8,446

Property Taxes

$1,311

HOA Dues

$0

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Property Information for 93 Upton Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly. Route 44 to Upton Road - Some directions may reference Elliot Road.
  • Elementary School: Ashford
  • Flood Zone: No
  • High School: Smith
  • Intermediate School: Per Board of Ed
  • Latitude: 41.855717
  • Longitude: -72.19994
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Park, Public Rec Facilities, Stables/Riding
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $15,733
Interior and Exterior Features
Exterior Features
  • Exterior Features: Wrap Around Deck, Gutters, Garden Area, Guest House, Stone Wall, Patio
  • Pool Description: Safety Fence, In Ground Pool
  • Waterfront Description: Brook, Walk to Water, View, Access
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Refrigerator, Dishwasher
  • Attic Description: Unfinished, Storage Space, Floored, Walk-In
  • Cooling System: Window Unit
  • Heat Type: Baseboard, Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 7
  • Interior Features: Cable - Available
  • Laundry Room Info: Lower Level
  • Rooms Additional: Foyer, Workshop
  • Rooms Total: 16
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Fireplace,Jack & Jill Bath,Wide Board Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: Fireplace,Jack & Jill Bath,Walk-In Closet,Wide Board Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 12
  • Room Features: Galley
  • Room Level: Other
  • Room Type: Kitchen
Room 5
  • Listing Key: 4F9F9A84D2366DA2E0631A01100AC419
  • Room Entry Order: 13
  • Room Features: Beams,Book Shelves,Built-Ins,Dining Area,Fireplace,Wide Board Floor
  • Room Level: Other
  • Room Type: Living Room
Room 6
  • Room Entry Order: 14
  • Room Features: 9 ft+ Ceilings,Vaulted Ceiling,Beams,Wide Board Floor
  • Room Level: Other
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 15
  • Room Level: Other
  • Room Type: Full Bath
Room 8
  • Room Entry Order: 16
  • Room Features: 9 ft+ Ceilings,Dining Area,Wood Stove,Full Bath
  • Room Level: Other
  • Room Type: Studio Apt
Room 9
  • Listing Key: 4F9F9A84D2366DA2E0631A01100AC419
  • Room Entry Order: 17
  • Room Features: 9 ft+ Ceilings,Vaulted Ceiling,Beams,Hardwood Floor
  • Room Level: Other
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 2
  • Room Features: Balcony/Deck,Built-Ins,Fireplace,Sliders,Wide Board Floor
  • Room Level: Main
  • Room Type: Family Room
Room 11
  • Room Entry Order: 3
  • Room Features: Balcony/Deck,Fireplace,Sliders,Wide Board Floor
  • Room Level: Main
  • Room Type: Formal Dining Room
Room 12
  • Room Entry Order: 4
  • Room Features: Remodeled,Built-Ins,Corian Counters,Dining Area,Pantry,Vinyl Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 13
  • Room Entry Order: 5
  • Room Features: Book Shelves,Built-Ins,Full Bath
  • Room Level: Main
  • Room Type: Office
Room 14
  • Room Entry Order: 6
  • Room Features: Balcony/Deck,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 15
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 16
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 17
  • Room Entry Order: 9
  • Room Features: Tile Floor
  • Room Level: Main
  • Room Type: Full Bath
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
  • In Law Access: Detached, Separate Entry
  • In Law Apartment: Yes
  • Sq Ft Description: 93 Upton Rd: 3,036sf; 90 Upton Rd: 730sf; 94 Upton Rd: 517sf
  • Living Area SQFT Per Public Records: 3036
Lot Information
  • Lot Description: Some Wetlands, Treed, Cleared, Professionally Landscaped, Rolling, Water View
  • Parcel Number: 1669803
  • Sq Ft Est Heated Above Grade: 4283.0
  • Sq Ft Total: 4283.0
  • Zoning: RA
Utilities
  • Energy Features: Generator Ready, Storm Windows
  • Heat Fuel Type: Electric, Oil
  • Hot Water Description: Electric, Domestic, 50 Gallon Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 93 Upton Road

DateEvent & SourcePriceAppreciation
Jun 3, 2026

Listed (Active)

SMARTMLS #24172504

$1,295,000—
Jun 3, 2026

Listed (Active)

SMARTMLS #24167939

$1,695,000—
DateEvent & SourcePrice
06/03/2026

Listed (Active)

SMARTMLS #24172504

$1,295,000
06/03/2026

Listed (Active)

SMARTMLS #24167939

$1,695,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 93 Upton Road

Taxable ValueLand$109,690Additions$185,570Total$295,260
Tax Record2024$10,742 ($895 / month)
Home Facts
Beds5Baths2Total Finished SqFt3,036 SqFtAbove Grade Finished SqFt3,036 SqFtUnfinished Basement SqFt1,766 SqFtStories1Lot Size8,529,048 SqFtStyleMiscellaneous ResidentialYear Built1733ZoningRACountyNORTHEASTERN CONNECTICUTAPNAFRD M:38 B:A L:3Fireplace TypeHas Fireplace

Schools near 93 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 93 Upton Road, Ashford, CT 06278

93 Upton Road is a single family home for sale in Ashford, CT 06278. This listing's school districts are Ashford School District, Regional School District 19. Nearby schools include Ashford School and E. O. Smith High School. 93 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, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Kiara C Rusconi

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.