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204 East Wakefield Boulevard

Winchester, Connecticut 06098

COMING SOON - NEW$959,900
Beds
2
Baths
1 | 1
SqFt
1,472
Acres
0.13
Year Built
1948
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Waterfront1 Fireplace

About This Home

Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with multiple sliders leading to a large wraparound waterfront deck, creating a seamless connection between indoor and outdoor living. The beautiful oak kitchen is highlighted by quartz countertops, newer stainless steel appliances, and an open layout that flows effortlessly into the main living areas, making it ideal for entertaining. Upstairs, the primary bedroom boasts soaring 12-foot cathedral ceilings and an abundance of windows overlooking the lake, providing a spectacular place to wake up each morning. Outside, the waterfront has been thoughtfully improved with an updated seawall that includes an aluminum dock, making it easy to enjoy boating, swimming, fishing. Highland Lake is a pristine 444-acre lake renowned for its clean water. Conveniently located just 45 minutes from Hartford and Bradley International Airport, and within easy reach of the Berkshires, Infinity Music Hall, the Warner Theatre, New York City, and Boston, this property offers the perfect blend of year-round living and a weekend retreat. A rare opportunity to create a lifetime of memories.

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Colonial
Year Built
1948
Days on Market
0 days
Beds
2
Baths
1 full · 1 half
Living Area
1,472 sq ft
Lot Size
0.13 acres
Property Taxes
$12,370 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

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

$959,900

vs $524,900 median

82.9% above median

Price / Sq Ft

$652

vs $265 median

2.5× the median

Days on Market

0 days

vs 39 days median

39 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

204 East Wakefield Boulevard, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,245

per month

  • Principal & Interest$4,894
  • Property Taxes$1,031
  • Insurance$320
  • 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
1948
New Construction
No/Resale
Living Area
1,472 sq ft

Schools

Elementary
Per Board of Ed
High
Gilbert

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Upper Level
Appliances
Oven/RangeRefrigeratorDishwasherWasherDryer
Basement
FullConcrete FloorFull With Walk-Out
In-Law Apartment
No

Exterior & Lot

Lot Size
0.13 acres
Zoning
HLD
Waterfront
Direct waterfront
Waterfront Details
LakeView
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
BlockConcrete
Exterior Features
Wrap Around DeckDeck
Lot Description
Water View

Listing & Financials

Property Taxes
$12,370 / Annually
Days on Market
0
MLS #
24194765
MLS Status
Coming Soon

Similar Properties

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Listed By

David Sartirana

(860) 806-0225

Northwest CT Realty

(860) 379-7245

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 6:10 PM UTC.