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Photo 1 of 19 — 150 Oak Street, Winchester, CT 06098
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150 Oak Street, Winchester, CT 06098

Litchfield County

Key Facts

11Beds
6Baths
5,233Sq Ft
1924Year Built
0.19Lot (acres)
4Garage

Description

*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!

Property Information

Property Type

Residential Income

Sub-Type

Multi Family

Style

Units are Side-by-Side / Other

Year Built

1924

Living Area

5,233 sq ft

Lot Size

0.19 acres

Garage Spaces

4

Parking Spaces

8

Zoning

R-3

Days on Market

73

MLS® Listing#

24166332

Property Features

Appliances

Electric Water HeaterGas Water Heater

Cooling

None

Heating

ElectricNatural GasHot Water

Basement

FullStorage SpaceUnfinishedConcrete

Parking

Off StreetOn StreetUnassigned

Patio

Porch

Lot Features

Sloped

Construction

Stucco

Foundation

Stone

Roof

Asphalt

Community

Tennis Court(s)

Sewer

Public Sewer

Water Source

Public

Schools

Elementary:
Per Board of Ed
Middle:
Per Board of Ed
High:
Per Board of Ed

Financial Details

HOA

None

Annual Taxes

$6,896

Parcel Number

926977

Directions

GPS friendly

Affordability Calculator

$109,800

Estimated monthly payment

$2,922/mo

Principal $439,200 · Est. interest $612,723 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Winchester, CT

$460,000
Median Listing Price
33
Median Days on Market
1,781
Median Sq Ft
$221
Median Price / Sq Ft
21
Active Listings
  • This home’s price is 19% above the area median.
  • Its price per sq ft is 52% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Winchester, CT.

Location

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Points of Interest in Winchester, CT

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Listing Courtesy: Turning Point Realty, LLC - (959) 799-1696

Presented by: Pamela Silvestri

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The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by SmartMLS. MLS® Listing#24166332. © 2026EXIT Realty®. All rights reserved.