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180 Shore Drive

Winchester, Connecticut 06098

ACTIVE - NEW$749,900
Beds
3
Baths
2
SqFt
1,131
Acres
0.12
Year Built
1978
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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WaterfrontDock / Mooring

About This Home

Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with quality finishes and thoughtful attention to detail throughout. Step inside to a bright, inviting interior filled with natural light from newer Andersen windows and doors. The beautifully renovated kitchen features modern appliances, sleek countertops, abundant cabinetry, and an open, welcoming feel that's perfect for entertaining after a day on the lake. Both full bathrooms have been tastefully remodeled, while LifeProof luxury plank flooring provides durability and easy maintenance. Enjoy year-round comfort with updated heating and central air conditioning. Outside is where this property truly shines! A newer deck and patio overlook Highland Lake, creating the perfect setting for morning coffee, summer dinners, sunsets, and unforgettable gatherings with family and friends. Step outside and enjoy direct access to one of Connecticut's most beautiful recreational lakes. Whether you're searching for a primary residence, weekend escape, or spectacular AirBnB, 180 Shore Dr delivers the lifestyle, location, and views that make waterfront ownership so special. Don't just buy a home - start living the Highland Lake lifestyle!

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Ranch
Year Built
1978
Days on Market
0 days
Beds
3
Baths
2 full
Living Area
1,131 sq ft
Lot Size
0.12 acres
Property Taxes
$11,567 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

27

18 active listings

Median $ / Sq Ft

$279

18 active listings

Sale-to-List Ratio

100.0%

96 sales

How this home compares

List Price

$749,900

vs $434,450 median

72.6% above median

Price / Sq Ft

$663

vs $279 median

2.4× the median

Days on Market

0 days

vs 27 days median

27 days fresher than median

Based on 18 active and 96 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 11, 2026.

Location

180 Shore Drive, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,109

per month

  • Principal & Interest$3,895
  • Property Taxes$964
  • Insurance$250
  • 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
1978
New Construction
No/Resale
Living Area
1,131 sq ft

Schools

Elementary
Harry P. Hinsdale
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Laundry
Lower Level
Laundry Location
next to downstairs bathroom 5x5 feet
Appliances
Electric RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullFully Finished
Additional Rooms
Laundry RoomWorkshop

Exterior & Lot

Lot Size
0.12 acres
Zoning
HL
Waterfront
Direct waterfront
Waterfront Details
LakeDock or MooringBeach RightsAssociation RequiredWater CommunityViewAccess
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Wood
Color
GRAY
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckLightingPatio
Lot Description
Level Lot

Listing & Financials

Property Taxes
$11,567 / Annually
Days on Market
0
MLS #
24206406
MLS Status
Active

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Listed By

Jacek Mikolajczyk

(860) 874-6646

Berkshire Hathaway NE Prop.

(860) 677-4949

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/11/2026. 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 9/11/2026 at 11:00 PM UTC.