26 Elm Street
Winchester, Connecticut 06098
- Beds
- 5
- Baths
- 3
- SqFt
- 2,496
- Acres
- 0.08
- Year Built
- 1920
- Property Type
- 3 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to 26 Elm Street, a newly renovated and legally converted three-family property in the heart of Winsted. This is a rare opportunity for investors or owner-occupants seeking a move-in-ready, income-producing asset with strong upside potential. Two of the units have been completely renovated, featuring updated interiors that appeal to today's tenants, while the exterior has also been recently improved, enhancing curb appeal and reducing near-term maintenance costs. The third unit provides additional income potential, making this a well-balanced investment with multiple revenue streams. The property has been legally converted to a 3-family, offering peace of mind and compliance for financing and long-term ownership. Prime Location & Rental Appeal Situated on Elm Street in Winsted, the property benefits from a convenient location close to downtown amenities, shopping, and dining. Easy access to commuter routes and nearby employment hubs helps drive consistent tenant demand. The area's small-town charm combined with accessibility makes it attractive for a wide range of renters. Strong Income Potential with two newly renovated units ready to command market rents and a third unit adding additional cash flow, this property is positioned for immediate income generation. Whether you're looking to expand your portfolio or live in one unit while renting the others, 26 Elm Street offers flexibility and solid returns.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Other
- Year Built
- 1920
- Days on Market
- 48 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 2,496 sq ft
- Lot Size
- 0.08 acres
- Property Taxes
- $3,712 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
6
7 under contract
Median List Price
$524,450
6 active listings
Median Closed Price
$305,000
17 sales
Median Days on Market
16
6 active listings
Median $ / Sq Ft
$191
6 active listings
Sale-to-List Ratio
100.0%
17 sales
How this home compares
List Price
$398,000
vs $524,450 median
24.1% below median
Price / Sq Ft
$159
vs $191 median
16.8% below median
Days on Market
48 days
vs 16 days median
32 days longer than median
Based on 6 active and 17 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
26 Elm Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,029
- Property Taxes$309
- Insurance$133
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- 3 Family
- Style
- Other
- Year Built
- 1920
- New Construction
- No/Resale
- Living Area
- 2,496 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Window Unit
- Basement
- Partial
Exterior & Lot
- Lot Size
- 0.08 acres
- Zoning
- CX
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Stucco
- Roof
- Flat
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $3,712 / Annually
- Days on Market
- 48
- MLS #
- 24182777
- MLS Status
- Under Contract
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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 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.