600 E Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 2
- Baths
- 1
- SqFt
- 1,361
- Acres
- 0.11
- Year Built
- 1920
- 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
Set along the highly desirable east side of Highland Lake, 600 East Wakefield Boulevard offers a unique opportunity to create a waterfront retreat tailored to your lifestyle. Brimming with charm and character, this home is ready for its next chapter and the fresh vision. Spend your days swimming, boating, and kayaking with easy access to the lake and the added benefit of a semi-private boat launch nearby. As the sun sets across the water each evening, you'll enjoy stunning panoramic views that make this location truly special. Whether you're dreaming of a cozy lakeside escape, a full-time waterfront home, or a thoughtful renovation project, this property provides the perfect foundation. Waterfront opportunities on Highland Lake are increasingly rare, making this a chance you won't want to miss! Subject to probate court approval. As-is sale.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1920
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 1 full
- Living Area
- 1,361 sq ft
- Lot Size
- 0.11 acres
- Property Taxes
- $8,678 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
10
13 under contract
Median List Price
$414,450
10 active listings
Median Closed Price
$320,500
102 sales
Median Days on Market
44
10 active listings
Median $ / Sq Ft
$209
10 active listings
Sale-to-List Ratio
100.0%
102 sales
How this home compares
List Price
$649,900
vs $414,450 median
56.8% above median
Price / Sq Ft
$478
vs $209 median
2.3× the median
Days on Market
0 days
vs 44 days median
44 days fresher than median
Based on 10 active and 102 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of August 13, 2026.
Location
600 E Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$3,351
- Property Taxes$723
- Insurance$217
- 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
- Cape Cod
- Year Built
- 1920
- New Construction
- No/Resale
- Living Area
- 1,361 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Wall Unit
- Laundry
- Main Level
- Appliances
- Electric RangeRefrigerator
- Basement
- None
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- HLD
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeViewAccess
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Construction
- Wood
- Color
- Brown
- Roof
- Asphalt Shingle
- Foundation
- None
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $8,678 / Annually
- Days on Market
- 0
- MLS #
- 24198153
- 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 8/13/2026. 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 8/13/2026 at 1:55 AM UTC.