55 Walnut Street
Winchester, Connecticut 06098
Reduced from $550,000
- Beds
- 5
- Baths
- 1 | 3
- SqFt
- 5,016
- Acres
- 0.56
- Year Built
- 1880
- Neighborhood
- Winsted
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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.
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.