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119 West Wakefield Boulevard

Winchester, Connecticut 06098

ACTIVE$849,900
Beds
4
Baths
2
SqFt
1,781
Acres
0.62
Year Built
1904
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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WaterfrontDock / Mooring2-Car GarageVirtual Tour

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
Multi-Family · Units on different Floors
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 · 2 total
Property Taxes
$11,910 / Annually

Market Snapshot

The Winchester Market

Multi-Family · trailing 12 months

Median Days on Market

16

6 active listings

Median $ / Sq Ft

$191

6 active listings

Sale-to-List Ratio

100.0%

17 sales

How this home compares

List Price

$849,900

vs $524,450 median

62.1% above median

Price / Sq Ft

$477

vs $191 median

2.5× the median

Days on Market

13 days

vs 16 days median

3 days fresher than median

Based on 6 active and 17 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of July 28, 2026.

Location

119 West Wakefield Boulevard, Winchester, Connecticut

Property + 10 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,609

per 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
Multi-Family
Subtype
Duplex
Style
Units on different Floors
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
Laundry
Basement Hook-Up(s)
Laundry Location
One Washer/Dryer Set Included
Basement
Partial

Exterior & Lot

Lot Size
0.62 acres
Zoning
HLD
Garage / Parking
2 garage spaces2 total parking spacesDetached GarageDrivewaySharedPaved
Waterfront
Direct waterfront
Waterfront Details
LakeDock or MooringView
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Color
White
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
BalconyShedWrap Around DeckDeckGuttersGarden AreaHot TubCovered Deck
Lot Description
Lightly WoodedTreedSloping LotWater View

Listing & Financials

Property Taxes
$11,910 / Annually
Days on Market
13
MLS #
24191163
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Mela Veltri Case

(203) 209-8403

KW Legacy Partners

(860) 313-0700

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 7:01 AM UTC.