150 Oak Street Winchester, CT $ 579,000
150 Oak Street
$ 579,000
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150 Oak Street

Winchester, CT, 06098
$ 579,000
Bedrooms11 Baths5.1 Sq 5,233

Monthly Estimate*

$ 3,565

150 Oak Street, Winchester, CT 06098 - Image 1
150 Oak Street, Winchester, CT 06098 - Image 2
150 Oak Street, Winchester, CT 06098 - Image 3
150 Oak Street, Winchester, CT 06098 - Image 4
150 Oak Street, Winchester, CT 06098 - Image 5
150 Oak Street, Winchester, CT 06098 - Image 6
150 Oak Street, Winchester, CT 06098 - Image 7
150 Oak Street, Winchester, CT 06098 - Image 8

Multi-Family Home for sale in Winchester, CT

for $579,000 with 11 bedrooms and 5 full baths, 1 half bath. This 5,233 square foot home was built in 1924 on a lot size of 0.19.

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! 48 HOURS Notice needed for all showings. Please do not disturb tenants. Property being sold "As Is". Conventional Financing or cash. Not all units have been photographed.

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Multi-Family Coming Soon

Price

$ 579,000

Bedrooms

11

Full Bath

5

Half Bath

1

Property Type

Multi-Family

Taxes

$ 6,706

Style

Lot Size

0.19

Year Built

1924

Town/City

Winchester

MLS | Web ID

24166332

Features
General
Zoning R-3
Neighborhood Winsted
County Litchfield
Tax Year July 2025-June 2026
Property Type Multi-Family For Sale
Status Coming Soon
Acres 0.19
Directions GPS friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 5233
Year Built 1924
Style Units are Side-by-Side Other
Year Built Source Public Records
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Interior
Cooling System None
Total Number of Units 5
Total Rooms 26
Basement Description Full Unfinished Storage Concrete Floor
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Exterior
Water Source Public Water Connected
Lot Description Sloping Lot
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* Excluded Features
List By
Pamela Silvestri

Listing Agent

Turning Point Realty, Llc

Broker

pamsilvestritprealty@gmail.com

Email

Affordability Calculator

$4,124
Per Month
86%
14%
0%
Monthly Principal & Interest
$3,565
Monthly Property Taxes
$559
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
4/20/2026$579,000 Listed Price

Map


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150 Oak Street, Winchester, CT, 06098 is a Multi-Family Home for sale at $579,000 with 5,233 sqft and a lot size of 0.19. 150 Oak Street has 11 bedrooms, 5.1 baths, and was built in 1924. The property's zip code is 06098 which is in Winchester, CT