*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! 48 HOURS Notice needed for all showings. Please do not disturb tenants or enter the property without showing agent present. Property being sold "As Is". Conventional Financing or cash. Not all units have been photographed. Each apartment has separate utilities.
For sale
Price cut: $30K (6/23)
$549,000
150 Oak Street, Winchester, CT 06098
11beds
5,233sqft
Multi Family
Built in 1924
-- sqft lot
$-- Zestimate®
$105/sqft
$-- HOA
What's special
High ceilingsSpacious roomsMostly hardwood floors
- 71 days |
- 296 |
- 8 |
Zillow last checked:
Listing updated:
Listed by:
Pamela Silvestri (959)799-1696,
Turning Point Realty, LLC 860-909-1162,
Suzie Larson 860-601-3730,
Turning Point Realty, LLC
Source: Smart MLS,MLS#: 24166332
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 11
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Heating
- Hot Water, Electric, Natural Gas
Cooling
- None
Appliances
- Included: Gas Water Heater, Electric Water Heater, Water Heater
- Laundry: In Basement, In Unit
Features
- Basement: Full,Unfinished,Storage Space,Concrete
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 5,233
- Total interior livable area: 5,233 sqft
- Finished area above ground: 5,233
Property
Parking
- Total spaces: 8
- Parking features: Detached, On Street, Off Street, Unassigned
- Garage spaces: 4
- Has uncovered spaces: Yes
Features
- Patio & porch: Porch
Lot
- Size: 8,276 Square Feet
- Features: Sloped
Details
- Parcel number: 926977
- Zoning: R-3
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Units are Side-by-Side,Other
- Property subtype: Multi Family
- Attached to another structure: Yes
Materials
- Stucco
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1924
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Library, Medical Facilities, Park, Playground, Public Rec Facilities, Shopping/Mall, Tennis Court(s), Near Public Transport
- Subdivision: Winsted
HOA
- Has HOA: No
Location
- Region: Winsted
Financial & listing details
- Price per square foot: $105/sqft
- Tax assessed value: $229,880
- Annual tax amount: $6,706
- Date on market: 4/20/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/23/2026 | Price change | $549,000-5.2%$105/sqft |
Source:  Smart MLS #24166332 Report a problem | ||
| 5/1/2026 | Listed for sale | $579,000+69.8%$111/sqft |
Source: Smart MLS #24166332 Report a problem | ||
| 8/13/2021 | Sold | $341,000-14.5%$65/sqft |
Source: Smart MLS #170383932 Report a problem | ||
| 6/1/2021 | Contingent | $399,000$76/sqft |
Source: Smart MLS #170383932 Report a problem | ||
| 3/26/2021 | Listed for sale | $399,000+4887.5%$76/sqft |
Source: Smart MLS #170383932 Report a problem | ||
| 7/30/2020 | Sold | $8,000-96.5%$2/sqft |
Source: Smart MLS #170265834 Report a problem | ||
| 6/28/2007 | Sold | $230,000$44/sqft |
Source: Smart MLS #A980233 Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 06098
Nearby schools
GreatSchools rating
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 0.2 mi
- NAPearson AcademyGrades: Distance: 0.3 mi
- NABatcheller Early Education CenterGrades: PK-2Distance: 1 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Connecticut
- Litchfield County
- Winsted
- 06098
- 150 Oak Street
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