720 Main Street
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 2
- SqFt
- 1,909
- Acres
- 0.07
- Year Built
- 1900
- Property Type
- 2 Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level commercial space is ready for its next chapter. Previously operating as a successful cafe, it includes a commercial kitchen setup with hood ventilation, refrigerator, restroom, and a spacious open layout that can easily accommodate a restaurant, coffee shop, boutique, salon, professional office, or countless other business concepts. Upstairs, you'll find a beautifully renovated three-bedroom apartment designed for modern comfort. Completely rebuilt down to the studs, the residence showcases a stylish new kitchen, updated windows, a newer roof, a private deck perfect for relaxing, and an energy-efficient on-demand hot water system. Separate gas and electric meters provide flexibility and convenience for owner-occupants or tenants alike. Just moments from Highland Lake, Route 44, shopping, dining, and all of Winsted's downtown attractions, this property offers incredible versatility. Live where you work, lease one or both units, or expand your investment portfolio with a property that offers excellent income-producing potential in a highly desirable location.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 15 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,909 sq ft
- Lot Size
- 0.07 acres
- Property Taxes
- $1,395 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
6
7 under contract
Median List Price
$524,450
6 active listings
Median Closed Price
$305,000
17 sales
Median Days on Market
16
6 active listings
Median $ / Sq Ft
$191
6 active listings
Sale-to-List Ratio
100.0%
17 sales
How this home compares
List Price
$395,000
vs $524,450 median
24.7% below median
Price / Sq Ft
$207
vs $191 median
8.4% above median
Days on Market
15 days
vs 16 days median
1 day fresher than median
Based on 6 active and 17 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
720 Main Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,014
- Property Taxes$116
- Insurance$132
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 1,909 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- None
Exterior & Lot
- Lot Size
- 0.07 acres
- Zoning
- CB-3
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt ShingleFlat
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $1,395 / Annually
- Days on Market
- 15
- MLS #
- 24190347
- MLS Status
- Active
Similar Properties
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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 5:25 AM UTC.