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837 East Wakefield Boulevard

Winchester, Connecticut 06098

ACTIVE - NEW$629,900
Beds
3
Baths
1 | 1
SqFt
1,168
Acres
0.76
Year Built
1930
Matt Caiola

Matt Caiola

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WaterfrontDock / Mooring

About This Home

Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake views, while a wonderful outdoor gathering area featuring a stone fireplace provides an ideal setting for entertaining family and friends. Just across the street, your private waterfront parcel takes lake living to another level with a 15' x 29' deck overlooking Highland Lake and a dock for your boat. Also located on the waterfront is a 240 sq. ft. structure with a half bath, offering excellent flexibility for storage, a lakeside retreat or additional sleeping accommodations. Spend your days boating, swimming, fishing or simply relaxing by the water, then retreat to the comfort of your home just steps away. A rare opportunity to enjoy your own private waterfront access and all that beautiful Highland Lake has to offer!

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Ranch
Year Built
1930
Days on Market
0 days
Beds
3
Baths
1 full · 1 half
Living Area
1,168 sq ft
Lot Size
0.76 acres
Property Taxes
$2,573 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

32

12 active listings

Median $ / Sq Ft

$248

12 active listings

Sale-to-List Ratio

100.0%

98 sales

How this home compares

List Price

$629,900

vs $514,500 median

22.4% above median

Price / Sq Ft

$539

vs $248 median

2.2× the median

Days on Market

0 days

vs 32 days median

32 days fresher than median

Based on 12 active and 98 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of August 26, 2026.

Location

837 East Wakefield Boulevard, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,659

per month

  • Principal & Interest$3,235
  • Property Taxes$214
  • Insurance$210
  • 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
Ranch
Year Built
1930
New Construction
No/Resale
Living Area
1,168 sq ft
Below Grade
260 sq ft

Schools

Elementary
Per Board of Ed
High
Gilbert

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Window Unit
Laundry
Lower Level
Appliances
Oven/RangeRefrigeratorDishwasherWasherDryer
Basement
PartialPartially FinishedPartial With Walk-Out
Interior Features
Open Floor Plan

Exterior & Lot

Lot Size
0.76 acres
Zoning
HLD
Waterfront
Direct waterfront
Waterfront Details
LakeDock or MooringView
Water Source
Private Well
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckStone Wall
Lot Description
TreedSloping LotWater View

Listing & Financials

Property Taxes
$2,573 / Annually
Days on Market
0
MLS #
24199152
MLS Status
Active

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 8/26/2026. 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 8/26/2026 at 5:20 PM UTC.