64 Wheeler Street
Winchester, Connecticut 06098
- Beds
- 4
- Baths
- 2
- SqFt
- 2,270
- Acres
- 0.33
- Year Built
- 1900
- Neighborhood
- Winsted
- Property Type
- 2 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
Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch, providing additional seasonal living space and a relaxing retreat. Outside, you'll find a level lot and a unique two-story barn with a full basement, offering exceptional storage, workshop space, or endless possibilities for hobbyists and contractors alike. Conveniently located just minutes from downtown, schools, shopping, dining, and everyday conveniences, this property is ideal whether you're looking to build your investment portfolio or live in one unit while generating rental income from the other. A rare opportunity to own a versatile multi-family property with timeless Victorian charm!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 1 day
- Beds
- 4
- Baths
- 2 full
- Living Area
- 2,270 sq ft
- Lot Size
- 0.33 acres
- Garage / Parking
- 3 garage · 6 total
- Property Taxes
- $5,082 / 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
$299,000
vs $524,450 median
43.0% below median
Price / Sq Ft
$132
vs $191 median
30.9% below median
Days on Market
1 day
vs 16 days median
15 days fresher 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
64 Wheeler Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,525
- Property Taxes$424
- 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
- 2,270 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Fireplaces
- 1
- Basement
- FullFull With Hatchway
Exterior & Lot
- Lot Size
- 0.33 acres
- Zoning
- R-3
- Garage / Parking
- 3 garage spaces6 total parking spacesBarnDetached GarageOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $5,082 / Annually
- Days on Market
- 1
- MLS #
- 24194728
- 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 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 5:25 AM UTC.