55 Walnut Street - Winchester, CT

$499,999

Beds

4.00

Baths

5,016

SqFt

0.56

Acres

Pricing Insight: Originally listed for $550,000, the price was last adjusted to $499,999 on January 25, 2026, a –$50,001 (9.1%) change, approximately 0 days ago. This property has been on the market for approximately 360 days.

55 Walnut Street, Winchester, CT is a 5-bed, 4-bath, 5,016 square foot home built in 1880 , featuring victorian architecture.

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

MLS #: 24071827

Offered Price: $499,999

Residence Type: Single Family

Architectural Style: Victorian

Living Area: 5,016 Sq. Ft.

Lot Size: 0.56 Acres

Neighborhood: Winsted

County: Litchfield

Year Built: 1880

Design & Construction: Frame

Heating: Steam

Cooling: None

Garage Spaces: 5

Price per Sq Ft as listed: $100

Estimated Tax: $10,602

Days on Market: 360

$339,900

4 Beds · 2 Baths · 2,345 Sq Ft

123 Wetmore Avenue, Winchester

$159,000

2 Beds · 2 Baths · 832 Sq Ft

8 Oak Street, Winchester

$1,695

3 Beds · 1 Baths · 1,059 Sq Ft

139 Main Street, Winchester

$1,800

2 Beds · 1 Baths · 38,896 Sq Ft

101 Whiting Street, Winchester

$825

1 Beds · 1 Baths · 650 Sq Ft

55 Wetmore Avenue, Winchester

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Steam

Fuel Tank Location: In Ground

Cooling System: None

Hot Water System: 65 Gallon Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $100 / Sq. Ft.

Tax assessed value: $363,440

Estimated Tax: $10,602

Architectural Style: Victorian

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1880

Living Area: 5,016 Sq. Ft.

Lot Size: 0.56 Acres

Fuel: Oil

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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: 26

Average Price: $311,097

Average DOM: 360 days

Complimentary CMAs, no obligation

Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

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Flood Risk Assessment

Location Analysis:

Inland Winchester location

Water Proximity:

No direct water access

Topography:

Standard terrain • 0.6 acres

Recommendations:

Consult FEMA Flood Maps for accurate zone info
Consider flood insurance based on professional assessment
Evaluate property drainage during inspection
Review local flood history with town officials

Risk Level: Low

Minimal flood risk indicators. Verify with FEMA flood maps.

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.

26

Homes For Sale

$311,097

Average List Price

Mechanicals & Utilities: Steam • Oil • None • Public Water Connected water

Exterior Features

Exterior Construction: Clapboard,Wood

Roof Type: Asphalt Shingle

Foundation: Stone

Garage: Barn,Off Street Parking (5 car)

Parking: 12 Total

Patio/Deck: Porch,Barn

Utilities: Water: Public Water Connected

Outbuildings: Porch,Barn

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

Steve Simos

Real Estate Advisor

Winchester • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0003

george@appzentric.com

Good afternoon Steve, I'm interested in
55 Walnut Street, Winchester, Connecticut

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