$579,000

150 Oak Street, Winchester, CT 06098

  • 11 beds |
  • 6 baths |
  • 5,233 sqft
  • Property Icon Multi-Family Home
  • Property Year Built Icon Built in 1924
  • Property Lot Size Icon8,276sqft lot
  • Property Parking Icon 4 car garage
  • Property Price Per Square Feet Icon $111/sqft
  • Property List Date Icon Listed 22 days ago

Property Description

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!

Listing Status:
Active
Date Added:
April 20, 2026
Data Last Updated:
May 13, 2026 at 12:52AM
Listing Office:
Turning Point Realty, LLC : (860) 909-1162
Listing Agent:
Pamela Silvestri : (959) 799-1696
MLS ID:
24166332
  • Laundry: Basement Hook-Up(s)Washer/Dryer Some Units
  • Basement: FullUnfinishedStorageConcrete Floor
  • A/C: None
  • Heating: Hot WaterElectricNatural Gas
  • Fireplace: Fireplaces: 0
  • General: Porch
  • Style: Units are Side-by-SideOther
  • Parking: Parking spaces: 8
  • Roofing: Asphalt Shingle
  • County: Litchfield
  • Zoning: R-3926977
  • Water: Public Water Connected
  • Sewer: Public Sewer Connected

This listing courtesy of Pamela Silvestri , Turning Point Realty, LLC

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location