119 West Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 4
- Baths
- 2
- SqFt
- 1,781
- Acres
- 0.62
- Year Built
- 1904
- Neighborhood
- Winsted
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating investment. Featuring modern upgrades throughout, the home boasts C/A, high-efficiency propane furnaces, newer appliances, windows, and siding-all designed for comfort and style. Inside, you'll find gorgeous details at every turn. The first-floor unit showcases a custom rustic kitchen with granite countertops, a Sub-Zero refrigerator, beverage fridge, gas range, and dishwasher. A luxurious marble-accented bathroom with a walk-in shower, two spacious bedrooms, and a large family room with French doors leading to a wraparound covered porch complete this level-perfect for soaking in those incredible views! The second-floor unit offers flexibility, featuring a kitchenette, dining room/office space, two additional bedrooms, and a family room with sliding doors opening to another covered porch-all with the same stunning lake vistas! Addt'l highlights include an oversized two-car detached garage with a carport, a hot tub (sold as-is), a level yard area, and a side deck. Situated just steps from the water, this home provides easy access to all lake activities. Rustic charm meets upscale living!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Colonial
- Year Built
- 1904
- Days on Market
- 13 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,781 sq ft
- Lot Size
- 0.62 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $11,910 / 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
$849,900
vs $524,900 median
61.9% above median
Price / Sq Ft
$477
vs $265 median
80.0% above median
Days on Market
13 days
vs 39 days median
26 days fresher 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
119 West Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,333
- Property Taxes$993
- Insurance$283
- 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
- Colonial
- Year Built
- 1904
- New Construction
- No/Resale
- Living Area
- 1,781 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Ceiling FansCentral Air
- Appliances
- Electric RangeGas RangeMicrowaveRefrigeratorSubzeroDishwasherWasherDryerWine Chiller
- Basement
- Partial
- Interior Features
- Auto Garage Door OpenerCable - AvailableSecurity System
Exterior & Lot
- Lot Size
- 0.62 acres
- Zoning
- HLD
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeDock or MooringView
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- PorchWrap Around DeckGuttersGarden AreaLightingHot TubCovered DeckFrench Doors
- Lot Description
- Lightly WoodedTreedSloping LotWater View
Listing & Financials
- Property Taxes
- $11,910 / Annually
- Days on Market
- 13
- MLS #
- 24191186
- MLS Status
- Active
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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 5:20 AM UTC.