8 Oak Street - Winchester, CT

$159,000

Beds

2.00

Baths

832

SqFt

0.03

Acres

Pricing Insight: Originally listed for $190,000, the price was last adjusted to $159,000 on January 26, 2026, a –$31,000 (16.3%) change, approximately 0 days ago. This property has been on the market for approximately 70 days. MLS reports 36 Days on Market (DOM) before it went under contract.

8 Oak Street, Winchester, CT is a 2-bed, 2-bath, 832 square foot home built in 1900 , featuring other architecture.

This home is within the Winchester school district. Local, with nearby schools including Per Board of Ed.

MLS #: 24140653

Offered Price: $159,000

Residence Type: Single Family

Architectural Style: Other

Living Area: 832 Sq. Ft.

Lot Size: 0.03 Acres

Neighborhood: Winsted

County: Litchfield

Year Built: 1900

Design & Construction: Frame

Heating: Baseboard

Cooling: None

Garage Spaces: 0

Price per Sq Ft as listed: $191

Estimated Tax: $1,819

Days on Market: 36

$499,999

5 Beds · 4 Baths · 5,016 Sq Ft

55 Walnut Street, Winchester

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Natural Gas

Fuel Type: Baseboard

Fuel Tank Location: Not specified

Cooling System: None

Hot Water System: Tank Size Unknown

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $191 / Sq. Ft.

Tax assessed value: $62,370

Estimated Tax: $1,819

Architectural Style: Other

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1900

Living Area: 832 Sq. Ft.

Lot Size: 0.03 Acres

Fuel: Natural Gas

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Winchester
Statistical modeling algorithms

Local Market Context

Active Listings: 27

Average Price: $311,389

Average DOM: 36 days

Complimentary CMAs, no obligation

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.

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Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 0.0 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

27

Homes For Sale

$311,389

Average List Price

Mechanicals & Utilities: Baseboard • Natural Gas • None • Public Water Connected water

Exterior Features

Exterior Construction: Vinyl Siding

Roof Type: Asphalt Shingle

Foundation: Concrete

Garage: Paved,Off Street Parking

Parking: 2 Total

Utilities: Water: Public Water Connected

Only motif connects you to a certified
"Local Market Expert"

George Antonopoulos

Real Estate Advisor

Winchester • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0001

george@appzentric.com

Good evening George, I'm interested in
8 Oak Street, Winchester, Connecticut

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