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39 South Main Street, Winchester, CT 06098

Multi-Family For Sale · Other

$749,900
$215/sqft

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7
Bedrooms
3
Bathrooms
3,486
Sq Ft
4.36
Acres
1900
Year Built

About This Home

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.

Listed by Ryan Horvay (860) 480-0357 with Smith & DeGroat Real Estate (516) 248-6905

Listing Snapshot

Price $749,900 Days on Market 358 days
Property Tax $4,899/yr Style Units on different Floors
Year Built 1900 Total Sq Ft 3,486
Lot Size 4.36 acres HOA Fees N/A
Bedrooms 7 Full Bathrooms 3
Total Rooms 13 Half Baths 0

Key Features

Outdoor
  • Porch-Wrap Around
  • Porch
  • Covered Deck

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Detached Garage

Systems & Utilities

Heat Hot Water
Fuel Natural Gas
Cooling None
Hot Water Domestic, Tankless Hotwater
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
Middle Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $408/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Mar 26, 2025 Listed $749,900

Frequently Asked Questions

How much does 39 South Main Street in Winchester, CT cost?
This property is listed at $749,900, which works out to $215 per square foot.
How many bedrooms does 39 South Main Street have?
This home has 7 bedrooms and 3 bathrooms.
What is the square footage of 39 South Main Street?
The home is 3,486 square feet, situated on 4.36 acres.
When was 39 South Main Street in Winchester built?
This property was built in 1900.
Is 39 South Main Street, Winchester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 39 South Main Street, Winchester in?
This home is served by the Winchester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 39 South Main Street, Winchester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Ryan Horvay · (860) 480-0357

Smith & DeGroat Real Estate · (516) 248-6905

MLS# 24083565 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Mar 2, 2026 7:48 PM UTC