18 Pratt Street
Winchester, Connecticut 06098
- Beds
- 5
- Baths
- 2
- SqFt
- 2,016
- Acres
- 0.17
- Year Built
- 1900
- Neighborhood
- Winsted
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great opportunity to live in one unit while generating rental income.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 2 full
- Living Area
- 2,016 sq ft
- Lot Size
- 0.17 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $2,959 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
7
2 under contract
Median List Price
$499,900
7 active listings
Median Closed Price
$324,900
21 sales
Median Days on Market
60
7 active listings
Median $ / Sq Ft
$175
7 active listings
Sale-to-List Ratio
100.3%
21 sales
How this home compares
List Price
$299,900
vs $499,900 median
40.0% below median
Price / Sq Ft
$149
vs $175 median
14.9% below median
Days on Market
0 days
vs 60 days median
60 days fresher than median
Based on 7 active and 21 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of September 11, 2026.
Location
18 Pratt Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$1,558
- Property Taxes$247
- Insurance$100
- 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
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 2,016 sq ft
Schools
- Elementary
- Mary P. Hinsdale
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- ElectricOil
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Washer/Dryer Some Units
- Basement
- FullFull With Walk-Out
Exterior & Lot
- Lot Size
- 0.17 acres
- Zoning
- TCR
- Garage / Parking
- 2 garage spaces4 total parking spacesDetached GarageDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $2,959 / Annually
- Days on Market
- 0
- MLS #
- 24206151
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/11/2026. 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 9/11/2026 at 8:25 PM UTC.