Back to search
39 South Main Street Winchester, CT $ 749,900
Share Save
$ 749,900 Get more info
39 South Main Street
$ 749,900
Back to search
Share Save

39 South Main Street

Winchester, CT, 06098
$ 749,900
Bedrooms7 Baths3.0 Sq 3,486

Monthly Estimate*

$ 4,617

39 South Main Street, Winchester, CT 06098 - Image 1
39 South Main Street, Winchester, CT 06098 - Image 2
39 South Main Street, Winchester, CT 06098 - Image 3
39 South Main Street, Winchester, CT 06098 - Image 4
39 South Main Street, Winchester, CT 06098 - Image 5
39 South Main Street, Winchester, CT 06098 - Image 6
39 South Main Street, Winchester, CT 06098 - Image 7
39 South Main Street, Winchester, CT 06098 - Image 8
39 South Main Street, Winchester, CT 06098 - Image 9
39 South Main Street, Winchester, CT 06098 - Image 10
39 South Main Street, Winchester, CT 06098 - Image 11
39 South Main Street, Winchester, CT 06098 - Image 12
39 South Main Street, Winchester, CT 06098 - Image 13
39 South Main Street, Winchester, CT 06098 - Image 14
39 South Main Street, Winchester, CT 06098 - Image 15
39 South Main Street, Winchester, CT 06098 - Image 16
39 South Main Street, Winchester, CT 06098 - Image 17
39 South Main Street, Winchester, CT 06098 - Image 18
39 South Main Street, Winchester, CT 06098 - Image 19
39 South Main Street, Winchester, CT 06098 - Image 20
39 South Main Street, Winchester, CT 06098 - Image 21
39 South Main Street, Winchester, CT 06098 - Image 22
39 South Main Street, Winchester, CT 06098 - Image 23
39 South Main Street, Winchester, CT 06098 - Image 24
39 South Main Street, Winchester, CT 06098 - Image 25
39 South Main Street, Winchester, CT 06098 - Image 26
39 South Main Street, Winchester, CT 06098 - Image 27
39 South Main Street, Winchester, CT 06098 - Image 28
39 South Main Street, Winchester, CT 06098 - Image 29
39 South Main Street, Winchester, CT 06098 - Image 30
39 South Main Street, Winchester, CT 06098 - Image 31
39 South Main Street, Winchester, CT 06098 - Image 32
39 South Main Street, Winchester, CT 06098 - Image 33
39 South Main Street, Winchester, CT 06098 - Image 34

Multi-Family Home for sale in Winchester, CT

for $749,900 with 7 bedrooms and 3 full baths. This 3,486 square foot home was built in 1900 on a lot size of 4.36.

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. High probability properties will be changed from TSF to Town Gateway zoning. This offers endless opportunity for residential and business growth. Potential access to rear property from Colony Dr. or Kittredge Lane. Property Addresses are: 39 South Main Street, South Main Street, & 18 Strong Terrace.

See more
Multi-Family Active

Price

$ 749,900

Bedrooms

7

Full Bath

3

Property Type

Multi-Family

Taxes

$ 4,899

Style

Lot Size

4.36

Year Built

1900

Town/City

Winchester

MLS | Web ID

24083565
Features
General
Zoning TSF
Neighborhood Winsted
County Litchfield
Tax Year July 2025-June 2026
Property Type Multi-Family For Sale
Status Active
Acres 4.36
Directions South Main to Strong Terrace. Drive off Strong.
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 3486
DOM 195
Year Built 1900
Style Units on different Floors
Year Built Source Public Records
See more
Interior
Cooling System None
Total Number of Units 2
Total Rooms 13
Basement Description Full Unfinished
See more
Exterior
Water Source Public Water Connected
Lot Description Secluded Corner Lot City Views Lightly Wooded Level Lot
See more
* Excluded Features
List By
Ryan Horvay

Listing Agent

Smith & Degroat Real Estate

Broker

rhorvay@sdnyrealty.com

Email

Affordability Calculator

$5,026
Per Month
92%
8%
0%
Monthly Principal & Interest
$4,617
Monthly Property Taxes
$408
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
6/26/2025$749,900 Listed Price

Map

More homes like this one

homes for you

See all
See all

39 South Main Street, Winchester, CT, 06098 is a Multi-Family Home for sale at $749,900 with 3,486 sqft and a lot size of 4.36. 39 South Main Street has 7 bedrooms, 3.0 baths, and was built in 1900. The property's zip code is 06098 which is in Winchester, CT

Get more info