147 E. Wakefield Boulevard
Winchester, Connecticut 06098
Reduced from $299,900
- Beds
- 2
- Baths
- 1
- SqFt
- 702
- Acres
- 0.24
- Year Built
- 1952
- Neighborhood
- Winsted
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring throughout, new roof, HW heater is only 4 years old, vinyl siding & fire pit. Year round lake living.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Cottage
- Year Built
- 1952
- Days on Market
- 74 days
- Beds
- 2
- Baths
- 1 full
- Living Area
- 702 sq ft
- Lot Size
- 0.24 acres
- Garage / Parking
- 2 total
- Property Taxes
- $2,273 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
Median Days on Market
39
12 active listings
Median $ / Sq Ft
$265
12 active listings
Sale-to-List Ratio
100.0%
103 sales
How this home compares
List Price
$269,900
vs $524,900 median
48.6% below median
Price / Sq Ft
$384
vs $265 median
44.9% above median
Days on Market
74 days
vs 39 days median
35 days longer than median
Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
147 E. Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,376
- Property Taxes$189
- Insurance$90
- 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
- Cottage
- Year Built
- 1952
- New Construction
- No/Resale
- Living Area
- 702 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling Fans
- Laundry
- Main Level
- Appliances
- Electric RangeMicrowaveRefrigeratorWasherDryer
- Basement
- FullUnfinishedDirt Floor
Exterior & Lot
- Lot Size
- 0.24 acres
- Zoning
- HLD
- Garage / Parking
- 2 total parking spacesDrivewayOff Street ParkingSharedGravel
- Waterfront Details
- Walk to WaterViewAccess
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Grey
- Roof
- Asphalt Shingle
- Foundation
- BlockStone
- Exterior Features
- ShedDeck
- Lot Description
- Rear LotInterior LotSloping Lot
Listing & Financials
- Property Taxes
- $2,273 / Annually
- Days on Market
- 74
- MLS #
- 24175908
- 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 6:05 AM UTC.