218 Oak Street
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 1
- SqFt
- 1,155
- Acres
- 0.16
- Year Built
- 1910
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Bring your design ideas to this classic shingle-sided home. With a fully functional interior, the main floor features an open kitchen-dining area with living room, fireplace and hardwood flooring. The side entrance has a dedicated area perfect for a mudroom to keep the main living space organized. The second level hosts two bedrooms with hardwood floors and a full bath with shower. The top level was previously used as the third bedroom and contains an extra large closet perfect for storage. There are dual entrances on the main level as well as a lower level walk out basement to the quaint and private back yard. A storage shed exists for your outdoor equipment or gardening supplies along with a covered cabana style sitting area. If you are looking for a blank canvas waiting for a fresh coat of paint and some finishing touches, this home is for you.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1910
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,155 sq ft
- Lot Size
- 0.16 acres
- Property Taxes
- $2,552 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
19
17 under contract
Median List Price
$410,000
19 active listings
Median Closed Price
$343,000
90 sales
Median Days on Market
46
19 active listings
Median $ / Sq Ft
$256
19 active listings
Sale-to-List Ratio
100.0%
90 sales
How this home compares
List Price
$235,000
vs $410,000 median
42.7% below median
Price / Sq Ft
$203
vs $256 median
20.7% below median
Days on Market
0 days
vs 46 days median
46 days fresher than median
Based on 19 active and 90 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of October 12, 2026.
Location
218 Oak Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$1,302
- Property Taxes$213
- Insurance$78
- 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
- Single Family
- Style
- Colonial
- Year Built
- 1910
- New Construction
- No/Resale
- Living Area
- 1,155 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 1
- Appliances
- Oven/RangeRefrigerator
- Basement
- PartialPartial With Walk-Out
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 0.16 acres
- Zoning
- TSF
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- ShingleWood
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Interior LotLevel Lot
Listing & Financials
- Property Taxes
- $2,552 / Annually
- Days on Market
- 0
- MLS #
- 24213052
- 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 10/12/2026. 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 10/12/2026 at 1:30 PM UTC.