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26 Elm Street

Winchester, Connecticut 06098

PENDING$398,000
Beds
5
Baths
3
SqFt
2,496
Acres
0.08
Year Built
1920
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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

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

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,471

per 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

Similar Properties

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

Listed By

Annie Simard

(860) 841-2633

LPT Realty

(877) 366-2213

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.