39 S Main St

Winchester, CT 06098

$749,900
Price
7
Beds
3,486 Sq. Ft.
$215 / Sq. Ft.
3,486
Sq. Ft.
$215
per Sq. Ft.
a front view of a house with a yard and garage
a view of a house with a yard
a view of yard with tree
a front view of a house with garden
a front view of a house with a yard
a view of a street with trees on both side of it
a view of yard covered with snow
a view of a backyard with trees
a view of an empty room with a fireplace
a view of a hallway with wooden floors and a fireplace
a view of a bedroom with wooden floor and a window
a view of a living room
a view of entryway with a front door
a utility room with window washer and dryer
a living room with furniture and wooden floor
a view of walk in closet
a view of walk in closet with clothes and shoes
a living room with furniture and a flat screen tv
a bathroom with a sink toilet and shower
a bed sitting in a bedroom next to a window
a view of staircase with three beds in wooden floor
a view of walk in closet
a kitchen with stainless steel appliances a table chairs and a refrigerator
a room with a wooden cabinet and shelf
a living room with furniture and a chandelier
a bathroom with a sink toilet and vanity
a living room with furniture and a flat screen tv
a view of entryway with wooden floor
a view of a hallway with windows and chandelier
an empty room with windows and closet
a view of a house with a yard covered in snow

Description

Three properties one price! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas heating system! 1.08 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with...Three properties one price! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas heating system! 1.08 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Tax & Square footage is total for all three properties.
  1. Listed by Ryan Horvay • Smith & DeGroat Real Estate
    P: (860)-480-0357 C: (860)-480-0357 rhorvay@sdnyrealty.com

Property Details for 39 South Main Street

Basement Description
Full, Unfinished
Direct Waterfront
No
Garages Number
2
Neighborhood
Winsted
Style
Units on different Floors
Garage Parking Info
Detached Garage
Swimming Pool
No
LISTING UPDATED: 10/07/2025 08:38 PM

Property Details for 39 South Main Street

StatusActive
MLS #24083565
Days on Market280
Taxes$4,899 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeMulti-Family / Other
Year Built1900
Lot Size4.36 AC / 189,921 SF
CountyLitchfield County

Location

Listing Courtesy of Smith & DeGroat Real Estate, Ryan Horvay
Add your commute

Building Information for 39 South Main Street

Stories-Residences2Year Built1900Building Size-Lot Size4.36 AC / 189,921 SF

Payment Calculator

$4,114 per month

30 year fixed, 6.28% Interest

Principal and Interest

$3,706

Property Taxes

$408

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 39 South Main Street

Summary
Property and Location
  • Acres Source: Owner
  • Directions: South Main to Strong Terrace. Drive off Strong.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.918255
  • Longitude: -73.05624
  • Middle Jr High School: Per Board of Ed
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $4,899
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Wrap Around, Porch, Covered Deck
Interior Features
  • Attic Description: Finished, Walk-up
  • Cooling System: None
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Rooms Total: 13
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Shake
  • Foundation Type: Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1900
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 3486
Lot Information
  • Lot Description: Secluded, Corner Lot, City Views, Lightly Wooded, Level Lot
  • Parcel Number: 929066
  • Sq Ft Est Heated Above Grade: 3486.0
  • Sq Ft Total: 3486.0
  • Zoning: TSF
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Domestic, Tankless Hotwater
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Tenant
  • Total Number of Units: 2
  • Total Rooms Multi Family: 13
Unit 1
  • Unit Entry Order: 1
  • Unit Full Baths: 3
  • Unit Modified Date: 03-26-2025
  • Unit Num Bedrms: 7
  • Unit Num Rooms: 13

Public Records for 39 South Main Street

Taxable ValueLand$26,950Additions$140,980Total$167,930
Tax Record2024$4,899 ($408 / month)
Home Facts
Baths3.5Total Finished SqFt3,486 SqFtAbove Grade Finished SqFt3,486 SqFtStories2Lot Size47,045 SqFtStyleDuplexYear Built1900ZoningR-3CountyLITCHFIELDAPNWSTR M:116 B:079 L:008Fireplace TypeHas Fireplace

Schools near 39 South Main Street

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Pearson Middle School
Public - 3 to 6
Mary P. Hinsdale School
Public - PK to 2
Batcheller Early Education Center
Public - PK to 2
Able School
Public - 1 to 4
Rating
School
Distance
Pearson Middle School
Public3 to 6

Mary P. Hinsdale School
PublicPK to 2

Batcheller Early Education Center
PublicPK to 2

Able School
Public1 to 4

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 39 South Main Street, Winchester, CT 06098

39 South Main Street is a multi-family home for sale in Winchester, CT 06098. This property was listed for sale on March 26, 2025 by Smith & DeGroat Real Estate, it's currently listed at $749,900. This listing's school district is Winchester School District. Nearby schools include Pearson Middle School, Mary P. Hinsdale School and Batcheller Early Education Center. 39 South Main Street is a 7-bed, 3-bath, 3,486 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.

Listing Courtesy of Smith & DeGroat Real Estate, Ryan Horvay

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.