156 Shore Drive Winchester, CT ^$ 789,000

156 Shore Drive

^$ 789,000

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Recently Listed

156 Shore Drive

Winchester, CT, 06098

^$ 789,000

Bedrooms5 Baths1.1 Sq 1,258

Monthly Estimate*

^$ 4,858

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Single Family Home for sale in Winchester, CT

for $789,000 with 5 bedrooms and 1 full bath, 1 half bath. This 1,258 square foot home was built in 1930 on a lot size of 0.1.

Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor activities, lakeside relaxation, or simply soaking in the sun. Don't miss out on this incredible opportunity - properties like this don't come around often!

Single Family Active

Price

^$ 789,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 10,577

Style

Lot Size

0.1

Year Built

1930

Town/City

Winchester

MLS | Web ID

24160676

Features

General

Zoning HLD

Neighborhood Winsted

County Litchfield

Tax Year July 2025-June 2026

Property Type Single Family For Sale

Status Active

Acres 0.1

Directions East Wakefield to Shore Drive

High School Per Board of Ed

City Winchester

Elementary School Per Board of Ed

Sq Ft Total 1258

DOM 1

Year Built 1930

Style Other

Year Built Source Public Records

Interior

Cooling System Ceiling Fans

Total Rooms 8

Basement Description None

Exterior

Water Source Public Water Connected

Lot Description Level Lot Water View

* Excluded Features

List By

Bryan Palladino

Listing Agent

Showcase Realty, Inc.

Broker

bryanpalladino@showcasect.com

Affordability Calculator

$5,739

Per Month

Monthly Principal & Interest: $4,858
Monthly Property Taxes: $881
Monthly Home Insurance: --

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Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Winchester, CT

Average List Price ^$360,969

Percent of Sale Price 54%

About Winchester, CT

11,188 Population

5% Since 2002

^$59,013 Median Income

45.79 Median Age

21% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

3092524 Elementary School

1232933 Middle School

Per Board of Ed High School High School

Pricing History

Date	Price	Price Change	Description
3/21/2026	$789,000		Listed Price

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156 Shore Drive, Winchester, CT, 06098 is a Single Family Home for sale at $789,000 with 1,258 sqft and a lot size of 0.1. 156 Shore Drive has 5 bedrooms, 1.1 baths, and was built in 1930. The property's zip code is 06098 which is in Winchester, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to a buying decision should be independently verified.

Information on this this page is provided by the Smart Multiple Listing Service, Inc. The information being provided is 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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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156 Shore Drive

Single Family Home for sale in Winchester, CT

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