46 Cherry Street
Winchester, Connecticut 06098
- Beds
- 4
- Baths
- 2
- SqFt
- 1,376
- Acres
- 0.37
- Year Built
- 1895
- 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
A wonderful opportunity to own a spacious antique Colonial with endless potential! This 4-bedroom, 2-full-bath home features a living room, dining room, and an eat-in kitchen, providing a solid foundation for your vision. While the home would benefit from updates, it offers an excellent opportunity for buyers to add their personal style and transform it into a truly standout property. Ideally located just a short walk from Highland Lake and Resha Beach, you'll enjoy convenient access to swimming, boating, and lakeside recreation. Strong surrounding property values further enhance this home's exceptional potential. Bring your ideas and restore this unique property to its full potential,
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1895
- Days on Market
- 26 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,376 sq ft
- Lot Size
- 0.37 acres
- Property Taxes
- $3,077 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
10
13 under contract
Median List Price
$382,450
10 active listings
Median Closed Price
$320,000
101 sales
Median Days on Market
51
10 active listings
Median $ / Sq Ft
$209
10 active listings
Sale-to-List Ratio
100.0%
101 sales
How this home compares
List Price
$199,900
vs $382,450 median
47.7% below median
Price / Sq Ft
$145
vs $209 median
30.6% below median
Days on Market
26 days
vs 51 days median
25 days fresher than median
Based on 10 active and 101 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of August 10, 2026.
Location
46 Cherry Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$1,031
- Property Taxes$256
- Insurance$67
- 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
- Subdivision
- HLD
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1895
- New Construction
- No/Resale
- Living Area
- 1,376 sq ft
Schools
- Elementary
- Mary P. Hinsdale
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Laundry
- Main Level
- Laundry Location
- main level
- Appliances
- Oven/RangeRefrigeratorWasherDryer
- Basement
- Full
- Accessibility
- Bath Grab Bars
Exterior & Lot
- Lot Size
- 0.37 acres
- Zoning
- R-3
- Waterfront Details
- Walk to Water
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Other
- Color
- Red
- Roof
- Shingle
- Foundation
- Stone
- Exterior Features
- ShedPorchGarden Area
- Lot Description
- TreedLevel Lot
Listing & Financials
- Property Taxes
- $3,077 / Annually
- Days on Market
- 26
- MLS #
- 24175743
- 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 8/10/2026. 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 8/10/2026 at 10:35 AM UTC.