150 Oak Street
Winchester, Connecticut 06098
Reduced from $579,000
- Beds
- 11
- Baths
- 5 | 1
- SqFt
- 5,233
- Acres
- 0.19
- Year Built
- 1924
- Neighborhood
- Winsted
- Property Type
- 5+ Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
*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!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Multi-Family · Units are Side-by-Side,Other
- Year Built
- 1924
- Days on Market
- 100 days
- Beds
- 11
- Baths
- 5 full · 1 half
- Living Area
- 5,233 sq ft
- Lot Size
- 0.19 acres
- Garage / Parking
- 4 garage · 8 total
- Property Taxes
- $6,896 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
6
7 under contract
Median List Price
$524,450
6 active listings
Median Closed Price
$305,000
17 sales
Median Days on Market
17
6 active listings
Median $ / Sq Ft
$191
6 active listings
Sale-to-List Ratio
100.0%
17 sales
How this home compares
List Price
$549,000
vs $524,450 median
In line with median
Price / Sq Ft
$105
vs $191 median
45.0% below median
Days on Market
100 days
vs 17 days median
83 days longer than median
Based on 6 active and 17 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of July 29, 2026.
Location
150 Oak Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,799
- Property Taxes$575
- Insurance$183
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Winsted
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- 5 Family+
- Style
- Units are Side-by-Side,Other
- Year Built
- 1924
- New Construction
- No/Resale
- Living Area
- 5,233 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- ElectricNatural Gas
- Cooling
- None
- Laundry
- Basement Hook-Up(s)Washer/Dryer Some Units
- Basement
- FullUnfinishedStorageConcrete Floor
Exterior & Lot
- Lot Size
- 0.19 acres
- Zoning
- R-3
- Garage / Parking
- 4 garage spaces8 total parking spacesDetached GarageOn Street ParkingOff Street ParkingUnassigned Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Stucco
- Color
- grey
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Porch
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $6,896 / Annually
- Days on Market
- 100
- MLS #
- 24166332
- MLS Status
- Active
Similar Properties
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Co-Listed By
Suzie Larson
Turning Point Realty, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/29/2026 at 12:40 PM UTC.