Winsted Multifamily Investment Opportunity

150 Oak St, Winchester, CT 06098

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For Sale

$579,000

Charming 5-unit apartment building in residential neighborhood. Fully rented.

Type:Multi Family

HighLights

Fully rented 5‑family apartment home in a desirable residential neighborhood.
Recent major upgrades including new roof, 4 hot water heaters, and 3 furnaces (2021‑2023).
Features original 1920's charm with original woodwork, high ceilings, and some hardwood floors.
Includes a 4‑bay detached garage, with rental income potential.
Convenient location: walking distance to Northwestern CT Community College and Downtown Winsted.
Easy access to Rte 8 and Western MA, including the Berkshires and MassPike.

We can help!

Listing Contact

Pamela Silvestri

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For Sale

$579,000

Charming 5-unit apartment building in residential neighborhood. Fully rented.

Type:Multi Family

Added:: Apr 21, 2026
Days on Market:: 53
Last Refresh:: Apr 21 at 1:01 am

Property Features for 150 Oak St

General Information

Standard status: Active
Property subtype: Multi Family

Building Details

Year Built: 1924

We can help!

Listing Contact

Pamela Silvestri

Listing agent Pamela Silvestri License #REB.0790888

Listing office Turning Point Realty, LLC

Listing date Apr 21, 2026

Source Elliman

Displayed information is deemed reliable but is not guaranteed and should be independently verified.

All listing content including descriptions, pricing, images are the copyrighted material of Turning Point Realty, LLC

HighLights

Fully rented 5‑family apartment home in a desirable residential neighborhood.
Recent major upgrades including new roof, 4 hot water heaters, and 3 furnaces (2021‑2023).
Features original 1920's charm with original woodwork, high ceilings, and some hardwood floors.
Includes a 4‑bay detached garage, with rental income potential.
Convenient location: walking distance to Northwestern CT Community College and Downtown Winsted.
Easy access to Rte 8 and Western MA, including the Berkshires and MassPike.

Overview

Located in a residential neighborhood of Winsted/Winchester, CT, 150 Oak St. is a fully rented, 5-family apartment building constructed in the 1920s. The property retains original woodwork, high ceilings, and some hardwood floors. Four of the units feature two bedrooms and a dining room with hallways connecting the spacious rooms. The fifth unit includes three bedrooms and one and a half baths with electric hot water. A detached four-bay garage is on the premises, with some bays rented separately, including one bay rented to a non-tenant. Recent updates between 2021 and 2023 include a new roof, four hot water heaters, and three furnaces. The property is located within walking distance of Northwestern CT Community College and Downtown Winsted, with nearby shopping and indoor and outdoor activities. Commuting is facilitated by proximity to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. The property is approximately 25 miles to Rte 20 and Becket, MA.

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Local Demand

City: Winchester
County: Litchfield
State: Connecticut
Longitude: -73.06285
Latitude: 41.926556

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What type of property is this?

Apartment building - Charming 5-unit apartment building in residential neighborhood. Fully rented.

Where is this apartment building located?

The property is located at 150 Oak St Winchester, CT.

What is the asking price?

The asking price for this property is $579,000.

What are key features of this property?

This property features: Fully rented 5‑family apartment home in a desirable residential neighborhood.; Recent major upgrades including new roof, 4 hot water heaters, and 3 furnaces (2021‑2023).; Features original 1920's charm with original woodwork, high ceilings, and some hardwood floors.