Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern cooking space. The carpet (installed in 2024) has been well maintained, and the home includes a hot water heater installed in 2022 for added peace of mind. Recent major updates include a new roof installed in 2023 with a 15-year transferable warranty, providing long-term value and security. Outside, the small property size means minimal upkeep-ideal for busy lifestyles or turnkey rental potential. Enjoy the convenience of being within walking distance to Main Street, giving you easy access to shops, dining, and community amenities.
Sold for $150,000
$150,000
8 Oak Street, Winchester, CT 06098
2beds
832sqft
Single Family Residence
Built in 1900
1,306.8 Square Feet Lot
$156,700 Zestimate®
$180/sqft
$1,619 Estimated rent
Home value
$156,700
$133,000 - $183,000
$1,619/mo
Zestimate® history
Owner options
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$1,619/mo
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$1,619/mo
Rent Zestimate®
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$1,073/mo
Est. payment
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$1,073/mo
Est. payment
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List your homeWhat's special
Granite countertopsNew gas stoveNew refrigeratorBrand-new wren kitchen cabinets
Zillow last checked:
Listing updated:
Listed by:
Austin Brochu (860)806-5097,
Sullivan Real Estate Inc 860-738-1902,
Kelly Sullivan 860-480-2449,
Sullivan Real Estate Inc
Bought with:
Jared Tedesco, RES.0821976
Litchfield County Real Estate
Source: Smart MLS,MLS#: 24140653
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Primary bedroom
- Level: Upper
Bedroom
- Level: Upper
Living room
- Level: Main
Heating
- Baseboard, Natural Gas
Cooling
- None
Appliances
- Included: Gas Range, Refrigerator
Features
- Basement: Full
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 832
- Total interior livable area: 832 sqft
- Finished area above ground: 832
Property
Parking
- Total spaces: 2
- Parking features: Paved, Off Street
Lot
- Size: 1,306 sqft
- Features: Level
Details
- Parcel number: 928027
- Zoning: R-3
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & neighborhood
Location
- Region: Winsted
- Subdivision: Winsted
Price history
| Date | Event | Price |
|---|---|---|
| 3/10/2026 | Sold | $150,000-5.7%$180/sqft |
Source:  Smart MLS #24140653 Report a problem | ||
| 12/28/2025 | Pending sale | $159,000$191/sqft |
Source: Smart MLS #24140653 Report a problem | ||
| 12/24/2025 | Listed for sale | $159,000$191/sqft |
Source: Smart MLS #24140653 Report a problem | ||
| 12/20/2025 | Pending sale | $159,000$191/sqft |
Source: Smart MLS #24140653 Report a problem | ||
| 12/15/2025 | Price change | $159,000-11.6%$191/sqft |
Source: Smart MLS #24140653 Report a problem | ||
| 12/3/2025 | Price change | $179,900-5.3%$216/sqft |
Source: Smart MLS #24140653 Report a problem | ||
| 11/20/2025 | Listed for sale | $190,000+153.3%$228/sqft |
Source: Smart MLS #24140653 Report a problem | ||
| 1/29/2021 | Sold | $75,000+0.1%$90/sqft |
Source: Smart MLS #170338009 Report a problem | ||
| 1/6/2021 | Contingent | $74,900$90/sqft |
Source:  Smart MLS #170338009 Report a problem | ||
| 12/8/2020 | Pending sale | $74,900$90/sqft |
Source: Hunter Real Estate, LLC #170338009 Report a problem | ||
| 12/8/2020 | Contingent | $74,900$90/sqft |
Source: Smart MLS #170338009 Report a problem | ||
| 12/5/2020 | Price change | $74,900-5.2%$90/sqft |
Source: Hunter Real Estate, LLC #170338009 Report a problem | ||
| 9/24/2020 | Pending sale | $79,000$95/sqft |
Source: Hunter Real Estate, LLC #170338009 Report a problem | ||
| 9/16/2020 | Listed for sale | $79,000+50.5%$95/sqft |
Source: Hunter Real Estate, LLC #170338009 Report a problem | ||
| 10/21/2014 | Sold | $52,500-9.5%$63/sqft |
Source: Smart MLS #G692665 Report a problem | ||
| 8/12/2014 | Listed for sale | $58,000-44.8%$70/sqft |
Source: Alliance Homes LLC #G692665 Report a problem | ||
| 3/24/2005 | Sold | $105,000+14.1%$126/sqft |
Source: Public Record Report a problem | ||
| 3/27/1989 | Sold | $92,000$111/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,819 +10.5% | $62,370 |
| 2024 | $1,646 | $62,370 |
| 2023 | $1,646 -8.1% | $62,370 +16.8% |
| 2022 | $1,791 | $53,410 |
| 2021 | $1,791 | $53,410 |
| 2020 | $1,791 | $53,410 |
| 2019 | $1,791 | $53,410 |
| 2018 | $1,791 +5.5% | $53,410 +5.5% |
| 2017 | $1,697 -4.9% | $50,610 -4.9% |
| 2016 | $1,784 +2.5% | $53,200 |
| 2015 | $1,740 +2.5% | $53,200 |
| 2014 | $1,698 +2.3% | $53,200 |
| 2013 | $1,660 +1.9% | $53,200 -16.9% |
| 2012 | $1,629 | $64,050 |
| 2011 | $1,629 | $64,050 |
| 2010 | $1,629 +3.1% | $64,050 |
| 2009 | $1,580 | $64,050 |
| 2008 | $1,580 +3.1% | $64,050 +43.2% |
| 2007 | $1,533 +2.8% | $44,730 |
| 2006 | $1,491 +11.8% | $44,730 +10.6% |
| 2005 | $1,334 +20.7% | $40,460 +10.3% |
| 2003 | $1,105 -23.8% | $36,680 -30.3% |
| 1995 | $1,450 | $52,610 |
Find assessor info on the county website
Neighborhood: 06098
Nearby schools
GreatSchools rating
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 0.4 mi
- NAPearson AcademyGrades: Distance: 0.4 mi
- NABatcheller Early Education CenterGrades: PK-2Distance: 0.7 mi
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$156,700
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$159,834
- Connecticut
- Litchfield County
- Winsted
- 06098
- 8 Oak Street
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