35 Prospect Street
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 1
- SqFt
- 1,201
- Acres
- 0.12
- Year Built
- 1875
- Neighborhood
- Winsted
- Property Type
- Single 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
3 bedroom home offering comfortable living with the convenience of gas heat as well as a wood stove and main level laundry. The layout provides plenty of space for everyday living, relaxing, and entertaining. Enjoy Highland Lake with Resha Beach just a half mile away, perfect for summer days by the water. A short drive takes you to the nearby boat launch, making it easy to enjoy boating, fishing, and all that the area's lakes have to offer.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Other
- Year Built
- 1875
- Days on Market
- 45 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,201 sq ft
- Lot Size
- 0.12 acres
- Garage / Parking
- 1 garage · 4 total
- Property Taxes
- $2,810 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
14
14 under contract
Median List Price
$412,500
14 active listings
Median Closed Price
$360,000
87 sales
Median Days on Market
64
14 active listings
Median $ / Sq Ft
$200
14 active listings
Sale-to-List Ratio
100.0%
87 sales
How this home compares
List Price
$239,900
vs $412,500 median
41.8% below median
Price / Sq Ft
$200
vs $200 median
In line with median
Days on Market
45 days
vs 64 days median
19 days fresher than median
Based on 14 active and 87 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of November 12, 2026.
Location
35 Prospect Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$1,300
- Property Taxes$234
- Insurance$80
- 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
- Single Family
- Style
- Other
- Year Built
- 1875
- New Construction
- No/Resale
- Living Area
- 1,201 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot WaterWood/Coal Stove
- Heat Fuel
- Natural Gas
- Cooling
- Ceiling Fans
- Laundry Location
- Main Level
- Appliances
- Oven/RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.12 acres
- Zoning
- TCR
- Garage / Parking
- 1 garage space4 total parking spacesDetached GarageDrivewayOff Street ParkingAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Open Lot
Listing & Financials
- Property Taxes
- $2,810 / Annually
- Days on Market
- 45
- MLS #
- 24210294
- MLS Status
- Under Contract - Continue to Show
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Kelly Sullivan
Sullivan Real Estate Inc
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/12/2026. 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 11/12/2026 at 10:25 PM UTC.