729 West Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 2
- Baths
- 1
- SqFt
- 1,128
- Acres
- 0.23
- Year Built
- 1900
- Neighborhood
- Winsted
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where every day feels like a vacation. Perfectly positioned on one of Connecticut's most sought-after lakes. This home needs some love, but has great bones! Bring your vision and create your dream home!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Cottage
- Year Built
- 1900
- Days on Market
- 50 days
- Beds
- 2
- Baths
- 1 full
- Living Area
- 1,128 sq ft
- Lot Size
- 0.23 acres
- Property Taxes
- $2,759 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
18
9 under contract
Median List Price
$414,450
18 active listings
Median Closed Price
$340,000
95 sales
Median Days on Market
30
18 active listings
Median $ / Sq Ft
$279
18 active listings
Sale-to-List Ratio
100.0%
95 sales
How this home compares
List Price
$320,000
vs $414,450 median
22.8% below median
Price / Sq Ft
$284
vs $279 median
In line with median
Days on Market
50 days
vs 30 days median
20 days longer than median
Based on 18 active and 95 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 15, 2026.
Location
729 West Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$1,662
- Property Taxes$230
- Insurance$107
- 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
- 1900
- New Construction
- No/Resale
- Living Area
- 1,128 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
- Refrigerator
- Basement
- Partial
Exterior & Lot
- Lot Size
- 0.23 acres
- Zoning
- HLD
- Waterfront Details
- View
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- TreedSloping LotWater View
Listing & Financials
- Property Taxes
- $2,759 / Annually
- Days on Market
- 50
- MLS #
- 24190178
- MLS Status
- Under Contract
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 9/15/2026. 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 9/15/2026 at 2:45 AM UTC.