00 Main Street
Winchester, Connecticut 06098
- Beds
- 0
- Baths
- 0
- SqFt
- —
- Acres
- 1.91
- Property Type
- Land

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial, industrial, mixed-use, and residential uses, subject to local approvals. Rich in local history, the property was once part of the site of the famed American Knife Company, a cornerstone of Winsted's manufacturing heritage. Today, it presents a unique opportunity to transform a historic location into a new destination for manufacturing, business, housing, or investment. All public utilities, including water, sewer, natural gas, and electric, are available, providing a significant advantage for future development. The extensive road frontage offers excellent visibility, accessibility, and site design potential. Winsted is open for business and eager to work with developers, investors, and entrepreneurs to bring new projects to life. Whether your vision is commercial, residential, industrial, or a combination thereof, this property provides the location, infrastructure, and zoning flexibility to make it a reality. A rare offering with exceptional frontage, utility access, development potential, and historical significance.
Key Facts
- City/Town
- Winchester
- Property Type
- Land
- Days on Market
- 47 days
- Beds
- 0
- Baths
- 0 baths
- Lot Size
- 1.91 acres
- Property Taxes
- $3,882 / Annually
Market Snapshot
The Winchester Market
Land · trailing 12 months
Active Listings
13
8 under contract
Median List Price
$250,000
13 active listings
Median Closed Price
$36,750
8 sales
Median Days on Market
88
13 active listings
Median $ / Sq Ft
--
13 active listings
Sale-to-List Ratio
85.9%
8 sales
How this home compares
List Price
$386,000
vs $250,000 median
54.4% above median
Price / Sq Ft
--
Median unavailable
Limited comparable data
Days on Market
47 days
vs 88 days median
41 days fresher than median
Based on 13 active and 8 closed sales (trailing 12 mo) of land in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
00 Main Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,968
- Property Taxes$324
- Insurance$129
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- County
- Litchfield
Residence
- Property Type
- Land
- Subtype
- Industrial
Exterior & Lot
- Lot Size
- 1.91 acres
- Zoning
- Town Gateway
- Waterfront
- Direct waterfront
- Waterfront Details
- River
- Water Source
- Public Water In Street
- Sewer
- Public Sewer In Street
- Lot Description
- Level LotCleared
Listing & Financials
- Property Taxes
- $3,882 / Annually
- Days on Market
- 47
- MLS #
- 24182990
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 6:50 AM UTC.