720 Main St

Winchester, CT 06098

$395,000
Price
3
Beds
1,909 Sq. Ft.
$207 / Sq. Ft.
1,909
Sq. Ft.
$207
per Sq. Ft.
front view of a house with a street
a front view of a house
a view of a brick building with a outdoor space
a view of a house with deck
a view of a hall with a car park table and chair
a view of a living room
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a bathroom with a toilet a sink and shower
a kitchen with a sink a stove and cabinets
a view of storage and utility room
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a view of storage and utility room
a hallway with a large window and furniture
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a view of an empty room with wooden floor
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor
an empty room with wooden floor and windows
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a bathroom with a sink and a mirror
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Description

Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe, retail, or service business! The second floor offers a spacious 3-bedroom apartment with many recent updates,...Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe, retail, or service business! The second floor offers a spacious 3-bedroom apartment with many recent updates, a new roof, windows, a deck, a kitchen, and an on-demand hot water system. The unit was renovated down to the studs. Separate gas and electric meters make it ideal for owner-occupier or investment use. On-street parking only, but surrounded by other downtown businesses with strong walkability and visibility. Excellent location near Highland Lake, Route 44, and all downtown amenities. Great opportunity to live and work in the same building or generate dual rental income. Bring your vision and make this Main Street property shine again! Also listed as a commercial property- MLS# 24138743
  1. Listed by Ryan Marconi • The Washington Agency
    P: (860)-960-6946 C: (860)-960-6946 ryan@thewashingtonagency.com

Property Details for 720 Main Street

Basement Description
None
Direct Waterfront
No
Neighborhood
N/A
Style
Units on different Floors, Other
Garage Parking Info
None
Swimming Pool
No
LISTING UPDATED: 11/29/2025 06:12 PM

Property Details for 720 Main Street

StatusActive
MLS #24138050
Days on Market41
Taxes$1,395 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeMulti-Family / 2 Family
Year Built1900
Lot Size0.07 AC / 3,049 SF
CountyLitchfield County

Location

Listing Courtesy of The Washington Agency, Ryan Marconi
Add your commute

Building Information for 720 Main Street

Stories-Residences2Year Built1900Building Size-Lot Size0.07 AC / 3,049 SF

Payment Calculator

$2,068 per month

30 year fixed, 6.28% Interest

Principal and Interest

$1,952

Property Taxes

$116

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 720 Main Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.92504
  • Longitude: -73.076163
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $1,395
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Cooling System: None
  • Heat Type: Baseboard, Hot Air
  • Attic YN: No
  • Fireplaces Total: 0
  • Rooms Total: 7
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Slab
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Flat
  • Year Built: 1900
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1909
Lot Information
  • Lot Description: Level Lot
  • Parcel Number: 927576
  • Sq Ft Est Heated Above Grade: 1909.0
  • Sq Ft Total: 1909.0
  • Zoning: CB-3
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, Domestic, Tankless Hotwater
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Vacant
  • Total Number of Units: 2
  • Total Rooms Multi Family: 7
Unit 1
  • Unit Appliances: Gas Range,Range Hood,Refrigerator
  • Unit Average Sq Ft: 760
  • Unit Entry Order: 2
  • Unit Full Baths: 1
  • Unit Modified Date: 11-29-2025
  • Unit Num Bedrms: 3
  • Unit Num Rooms: 5
  • Unit Occupied By: Vacant
Unit 2
  • Unit Average Sq Ft: 1149
  • Unit Entry Order: 1
  • Unit Half Baths: 1
  • Unit Modified Date: 11-29-2025
  • Unit Num Bedrms: 0
  • Unit Num Rooms: 2
  • Unit Occupied By: Vacant

Property History for 720 Main Street

DateEvent & SourcePriceAppreciation
Jun 1, 2024

Closed (Public Record)

Public Record #1533849710

$115,000

+13.2% / yr

Oct 31, 2016

Closed (Public Record)

Public Record #582655194

$45,000—
DateEvent & SourcePrice
06/01/2024

Closed (Public Record)

Public Record #1533849710

$115,000

+13.2% / yr

10/31/2016

Closed (Public Record)

Public Record #582655194

$45,000

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

Public Records for 720 Main Street

Taxable ValueLand$21,000Additions$26,810Total$47,810
Tax Record2024$1,395 ($116 / month)
Home Facts
Total Finished SqFt1,909 SqFtAbove Grade Finished SqFt1,909 SqFtStories2Lot Size3,049 SqFtStyleMiscellaneous CommercialYear Built1900ZoningCB-3CountyLITCHFIELDAPNWSTR M:110 B:047 L:011

Schools near 720 Main Street

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Pearson Middle School
Public - 3 to 6
Bridges School 2
Public - 2 to 6
Mary P. Hinsdale School
Public - PK to 2
Batcheller Early Education Center
Public - PK to 2
Rating
School
Distance
Pearson Middle School
Public3 to 6

Bridges School 2
Public2 to 6

Mary P. Hinsdale School
PublicPK to 2

Batcheller Early Education Center
PublicPK to 2

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 720 Main Street, Winchester, CT 06098

720 Main Street is a multi-family home for sale in Winchester, CT 06098. This property was listed for sale on November 12, 2025 by The Washington Agency, it's currently listed at $395,000. It has been on the market for a total of 41 days and was last sold on June 1, 2024. This listing's school district is Winchester School District. Nearby schools include Pearson Middle School, Bridges School 2 and Mary P. Hinsdale School. 720 Main Street is a 3-bed, 2-bath, 1,909 sqft multi-family home built in 1900.

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 makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of The Washington Agency, Ryan Marconi

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.