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55 Walnut Street

Winchester, Connecticut 06098

ACTIVE$449,000

Reduced from $550,000

Beds
5
Baths
1 | 3
SqFt
5,016
Acres
0.56
Year Built
1880
Matt Caiola

Matt Caiola

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5-Car GaragePrice Reduced

About This Home

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.

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Victorian
Year Built
1880
Days on Market
544 days
Beds
5
Baths
1 full · 3 half
Living Area
5,016 sq ft
Lot Size
0.56 acres
Garage / Parking
5 garage · 12 total
Property Taxes
$10,602 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

40

12 active listings

Median $ / Sq Ft

$265

12 active listings

Sale-to-List Ratio

100.0%

103 sales

How this home compares

List Price

$449,000

vs $524,900 median

14.5% below median

Price / Sq Ft

$90

vs $265 median

66.0% below median

Days on Market

544 days

vs 40 days median

504 days longer than median

Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 29, 2026.

Location

55 Walnut Street, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,323

per month

  • Principal & Interest$2,289
  • Property Taxes$884
  • Insurance$150
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Winchester
Neighborhood
Winsted
County
Litchfield

Residence

Property Type
Single Family
Style
Victorian
Year Built
1880
New Construction
No/Resale
Living Area
5,016 sq ft

Schools

Elementary
Per Board of Ed
High
Gilbert

Interior

Heating
Steam
Heat Fuel
Oil
Cooling
None
Appliances
None
Basement
FullWalk-out

Exterior & Lot

Lot Size
0.56 acres
Zoning
TCR
Garage / Parking
5 garage spaces12 total parking spacesBarnOff Street Parking
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
ClapboardWood
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
PorchBarn
Lot Description
Level Lot

Listing & Financials

Property Taxes
$10,602 / Annually
Days on Market
544
MLS #
24071827
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

David Sartirana

(860) 806-0225

Northwest CT Realty

(860) 379-7245

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/29/2026 at 10:10 AM UTC.