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150 Oak Street, Winchester, CT 06098

Multi-Family For Sale · 5 Family+

$579,000
$111/sqft

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11
Bedrooms
6
Bathrooms
5,233
Sq Ft
0.19
Acres
1924
Year Built

About This Home

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, some 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!

Listed by Pamela Silvestri (959) 799-1696 with Turning Point Realty, LLC (860) 909-1162

Listing Snapshot

Price $579,000 Days on Market —
Property Tax $6,706/yr Style Units are Side-by-Side,Other
Year Built 1924 Total Sq Ft 5,233
Lot Size 0.19 acres HOA Fees N/A
Bedrooms 11 Full Bathrooms 5
Total Rooms 26 Half Baths 1

Key Features

Outdoor
  • Porch
Nearby
  • Library
  • Medical Facilities
  • Park
  • Playground/Tot Lot
  • Public Rec Facilities
  • Shopping/Mall
  • Tennis Courts
  • Walk to Bus Lines

Structure & Parking

Construction Stucco
Roof Asphalt Shingle
Garage Spaces 4
Garage Type Detached Garage, On Street Parking, Off Street Parking, Unassigned Parking

Systems & Utilities

Heat Hot Water
Fuel Electric, Natural Gas
Cooling None
Hot Water Natural Gas, Electric, 40 Gallon Tank
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
Middle Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $559/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Apr 20, 2026 Listed $579,000

Frequently Asked Questions

How much does 150 Oak Street in Winchester, CT cost?
This property is listed at $579,000, which works out to $111 per square foot.
How many bedrooms does 150 Oak Street have?
This home has 11 bedrooms and 6 bathrooms.
What is the square footage of 150 Oak Street?
The home is 5,233 square feet, situated on 0.19 acres.
When was 150 Oak Street in Winchester built?
This property was built in 1924.
Is 150 Oak Street, Winchester, CT still available?
The current MLS status of this property is "Coming Soon". Contact RYZE Realty Group for the latest availability.
What school district is 150 Oak Street, Winchester in?
This home is served by the Winchester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 150 Oak Street, Winchester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Pamela Silvestri · (959) 799-1696

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

MLS# 24166332 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Apr 20, 2026 12:02 PM UTC