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150 Oak Street, 
Winchester, CT 06098

$579,000

11

Beds

6

Baths

5,233

Sq Ft

Multi-Family

Active

Listed by

Pamela Silvestri, (959) 799-1696

, 

Suzie Larson

Turning Point Realty, LLC., (860) 909-1162

(860) 909-1162

Last updated:

May 23, 2026, 11:31 AM

MLS#

24166332

Source:

CT

About This Home

150 Oak Street

150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

Home Facts

Multi-Family

6 Baths

11 Bedrooms

Built in 1924

Price Summary

579,000

$110 per Sq. Ft.

MLS #:

24166332

Last Updated:

May 23, 2026, 11:31 AM

Added:

a month ago

Rooms & Interior

Bedrooms

Total Bedrooms:

11

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

5

Interior

Living Area:

5,233 Sq. Ft.

Structure

Structure

Architectural Style:

Units are Side-by-Side

Building Area:

5,233 Sq. Ft.

Year Built:

1924

Lot

Lot Size (Sq. Ft):

8,276

Finances & Disclosures

Finances

Price:

$579,000

Price per Sq. Ft:

$110 per Sq. Ft.

Source:CT
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.