99 High Street
Winchester, Connecticut 06098
- Beds
- 14
- Baths
- 10 | 2
- SqFt
- 3,012
- Acres
- 0.23
- Year Built
- 1958
- Neighborhood
- Winsted
- Property Type
- 4 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
A multi family residential property. The Building was built in 1958 and includes 4 units as well as a garage for multi purpose storage use. It has a large swing up garage door for excellent storage. There is also a small office with an interior bathroom. 1 unit is a 2 bedroom 1.5 bath. 3 units are a 1 bedroom, 1 bath. Each unit is rented with a stable long term paying tenant. The garage is also rented to a long term tenant. The driveway parking area was recently redone with new concrete for parking access. The exterior was recently painted and has been well maintained, a new furnace has been added as well, 3 of the 4 units have been updated.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Multi-Family · 4updown - Unit(s) per Floor
- Year Built
- 1958
- Days on Market
- 0 days
- Beds
- 14
- Baths
- 10 full · 2 half
- Living Area
- 3,012 sq ft
- Lot Size
- 0.23 acres
- Garage / Parking
- 8 garage
- Property Taxes
- $7,016 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
9
2 under contract
Median List Price
$499,900
9 active listings
Median Closed Price
$324,950
20 sales
Median Days on Market
72
9 active listings
Median $ / Sq Ft
$175
9 active listings
Sale-to-List Ratio
100.2%
20 sales
How this home compares
List Price
$575,000
vs $499,900 median
15.0% above median
Price / Sq Ft
$191
vs $175 median
9.1% above median
Days on Market
0 days
vs 72 days median
72 days fresher than median
Based on 9 active and 20 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of September 25, 2026.
Location
99 High Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$3,070
- Property Taxes$585
- Insurance$192
- 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
- Subdivision
- Hartford
Residence
- Property Type
- Multi-Family
- Subtype
- Quadruplex
- Style
- 4updown - Unit(s) per Floor
- Year Built
- 1958
- New Construction
- No/Resale
- Living Area
- 3,012 sq ft
Schools
- Elementary
- Harry P. Hinsdale
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- No Heat
- Cooling
- None
- Basement
- None
Exterior & Lot
- Lot Size
- 0.23 acres
- Zoning
- Commercial
- Garage / Parking
- 8 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Wood
- Roof
- Shingle
- Foundation
- None
- Lot Description
- Corner Lot
Listing & Financials
- Property Taxes
- $7,016 / Annually
- Days on Market
- 0
- MLS #
- 24209933
- 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 9/25/2026. 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 9/25/2026 at 11:00 PM UTC.