180 Shore Drive
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 2
- SqFt
- 1,131
- Acres
- 0.12
- Year Built
- 1978
- Neighborhood
- Winsted
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
18
9 under contract
Median List Price
$434,450
18 active listings
Median Closed Price
$335,000
96 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per 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
Similar Properties
Homes with a close match in area, property type, and price.
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.