Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
11 Beds
6 Baths
5,233 sqft

$549,000

150 Oak Street, Winchester CT, 06098

Price per sqft$104.91
Built in1924
Property size5,233 sqft
Property typeMulti-family

Overview

Active

Listed Apr 20, 2026

Updated Aug 26

*PRICE REDUCTION* 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 3-4 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!

$3,653/mo

Est. mortgage payment based on a $549,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
24166332

Interior Features

Bedrooms
11
Bathrooms
6
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.19 Acres

Other Property Details

Taxes
$6,896
Tax Frequency
Annually
Garage
Yes
MLS provider logo

Listed by Pamela Silvestri with Turning Point Realty, LLC (959) 799-1696

The IDX display contains information sourced from SmartMLS, Inc. as of 8/26/2026. This information is for personal, non-commercial use only and may not be used for any purpose other than identifying properties the viewer may be interested in purchasing. MLS data is generally considered reliable but is not guaranteed accurate by the MLS. Buyers are responsible for verifying all information and should conduct their own investigation or consult a professional. Some MLS data may have been provided by sources other than the listing agent. Unless stated in writing, the Broker/Agent has not verified information obtained from outside sources. The Broker/Agent may or may not have been the listing and/or selling agent, and cannot guarantee the accuracy of any property location shown on a map. Any offer of compensation is made only to participants of the MLS where the listing is filed.

©2026 SmartMLS, Inc. All rights reserved.

Data last updated on 8/26/2026 at 2:48 AM UTC.

Powered by Luxury Presence