436 Main St

Winchester, CT 06098

$750,000
Price
4
Beds
5,389 Sq. Ft.
$139 / Sq. Ft.
5,389
Sq. Ft.
$139
per Sq. Ft.
a front view of a brick building with large windows
a view of a building with a window
a view of a building with a outdoor space
a close view of stove top oven
a kitchen with lots of counter space and stainless steel appliances
a kitchen with lots of counter top space
a view of water heater room
a close view of water heater room
a room with stainless steel appliances kitchen island granite countertop a stove and a sink
a kitchen with a stove and a refrigerator

Description

One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications...One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs) Price includes thriving restaurant with 10 year track record with all equipment included. See attachment for equipment list
  1. Listed by Anthony Gioia • The Washington Agency
    P: (860)-459-8911 C: (860)-459-8911 tony@thewashingtonagency.com

Property Details for 436 Main Street

Basement Description
Crawl Space
Direct Waterfront
No
Neighborhood
N/A
Style
Units on different Floors
Garage Parking Info
None
Swimming Pool
No
LISTING UPDATED: 10/28/2025 01:50 PM

Property Details for 436 Main Street

StatusActive
MLS #24135030
Days on Market70
Taxes$4,690 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeMulti-Family / 2 Family
Year Built1910
Lot Size0.10 AC / 4,356 SF
CountyLitchfield County

Location

Listing Courtesy of The Washington Agency, Anthony Gioia
Add your commute

Building Information for 436 Main Street

Stories-Residences5Year Built1910Building Size-Lot Size0.10 AC / 4,356 SF

Payment Calculator

$4,046 per month

30 year fixed, 6.15% Interest

Principal and Interest

$3,655

Property Taxes

$391

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 436 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: 41.921101
  • Longitude: -73.071752
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $4,690
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Cooling System: Ductless
  • Heat Type: Heat Pump, Hot Air
  • Attic YN: No
  • Fireplaces Total: 0
  • Laundry Room Info: None
  • Rooms Total: 14
Room 5
  • Listing Key: 41AE91930951C4E3E0631A01100A4E30
Property
Property and Assessments
  • Construction Description: Brick
  • Exterior Siding: Brick
  • Foundation Type: Brick
  • New Construction Type: No/Resale
  • Roof: Flat
  • Year Built: 1910
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 5389
Lot Information
  • Lot Description: Level Lot
  • Parcel Number: 927702
  • Sq Ft Est Heated Above Grade: 5389.0
  • Sq Ft Total: 5389.0
  • Zoning: CB-3
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: 40 Gallon Tank
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Tenant
  • Total Number of Units: 5
  • Total Rooms Multi Family: 14
Unit 1
  • Unit Entry Order: 1
  • Unit Modified Date: 10-28-2025
  • Unit Monthly Rent: $675
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 3
  • Unit Occupied By: Tenant
Unit 2
  • Unit Entry Order: 3
  • Unit Modified Date: 10-28-2025
  • Unit Monthly Rent: $550
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 3
  • Unit Occupied By: Tenant
Unit 3
  • Unit Entry Order: 5
  • Unit Half Baths: 2
  • Unit Modified Date: 10-28-2025
  • Unit Monthly Rent: $2,800
  • Unit Num Bedrms: 0
  • Unit Num Rooms: 4
  • Unit Occupied By: Owner
Unit 4
  • Unit Entry Order: 4
  • Unit Modified Date: 10-28-2025
  • Unit Monthly Rent: $475
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 1
  • Unit Occupied By: Tenant
Unit 5
  • Unit Entry Order: 2
  • Unit Modified Date: 10-28-2025
  • Unit Monthly Rent: $1,275
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 3
  • Unit Occupied By: Tenant

Property History for 436 Main Street

DateEvent & SourcePriceAppreciation
Oct 29, 2021

Closed (Public Record)

Public Record #1476247908

$225,000—
DateEvent & SourcePrice
10/29/2021

Closed (Public Record)

Public Record #1476247908

$225,000

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

Public Records for 436 Main Street

Taxable ValueLand$22,540Additions$92,890Total$115,430
Tax Record2021$3,872 ($323 / month)
Home Facts
Total Finished SqFt5,389 SqFtAbove Grade Finished SqFt5,389 SqFtStories3Lot Size4,356 SqFtStyleMiscellaneous CommercialYear Built1910ZoningCB-3CountyLITCHFIELDAPNWINC M:110 B:052 L:021

Schools near 436 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 436 Main Street, Winchester, CT 06098

436 Main Street is a multi-family home for sale in Winchester, CT 06098. This property was listed for sale on October 27, 2025 by The Washington Agency, it's currently listed at $750,000. It has been on the market for a total of 70 days and was last sold on October 29, 2021. This listing's school district is Winchester School District. Nearby schools include Pearson Middle School, Bridges School 2 and Mary P. Hinsdale School. 436 Main Street is a 4-bed, 2-bath, 5,389 sqft multi-family home built in 1910.

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, Anthony Gioia

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.