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720 Main Street

Winchester, Connecticut 06098

ACTIVE$395,000
Beds
3
Baths
2
SqFt
1,909
Acres
0.07
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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

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

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,262

per 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

Homes with a close match in area, property type, and price.

Listed By

Arlene Gonzalez

The Gonzalez Property Group

(718) 650-0292

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.