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!
Sold for $691,000
$691,000
156 Shore Drive, Winchester, CT 06098
5beds
1,258sqft
Single Family Residence
Built in 1930
4,356 Square Feet Lot
$693,500 Zestimate®
$549/sqft
$2,539 Estimated rent
Home value
$693,500
$631,000 - $763,000
$2,539/mo
Zestimate® history
Owner options
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$2,539/mo
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$4,613/mo
Est. payment
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$4,613/mo
Est. payment
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List your homeWhat's special
Waterfront propertyBreathtaking western exposureDirect waterfront accessFlat easy-to-maintain lot
Zillow last checked:
Listing updated:
Listed by:
Bryan Palladino (475)204-6145,
Showcase Realty, Inc. 860-274-7000
Bought with:
Annie Simard, RES.0822960
LPT Realty
Source: Smart MLS,MLS#: 24160676
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Primary bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Dining room
- Level: Main
Living room
- Level: Main
Heating
- Forced Air, Oil
Cooling
- Ceiling Fan(s)
Appliances
- Included: Oven/Range, Refrigerator, Washer, Dryer, Electric Water Heater, Water Heater
- Laundry: Main Level
Features
- Basement: None
- Attic: None
- Number of fireplaces: 1
Interior area
- Total structure area: 1,258
- Total interior livable area: 1,258 sqft
- Finished area above ground: 1,258
Property
Parking
- Total spaces: 6
- Parking features: Off Street, Driveway, Unpaved, Private
- Has uncovered spaces: Yes
Features
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Lake
Lot
- Size: 4,356 sqft
- Features: Level, In Flood Zone
Details
- Parcel number: 928497
- Zoning: HLD
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other
- Property subtype: Single Family Residence
Materials
- Stone, Stucco
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1930
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & neighborhood
Location
- Region: Winsted
- Subdivision: Winsted
Price history
| Date | Event | Price |
|---|---|---|
| 5/21/2026 | Sold | $691,000-11.4%$549/sqft |
Source:  Smart MLS #24160676 Report a problem | ||
| 4/21/2026 | Pending sale | $779,900$620/sqft |
Source: Smart MLS #24160676 Report a problem | ||
| 4/1/2026 | Price change | $779,900-1.2%$620/sqft |
Source: Smart MLS #24160676 Report a problem | ||
| 3/21/2026 | Listed for sale | $789,000+97.3%$627/sqft |
Source: Smart MLS #24160676 Report a problem | ||
| 10/2/2014 | Sold | $400,000-9.2%$318/sqft |
Source: Smart MLS #L150185 Report a problem | ||
| 8/11/2014 | Pending sale | $440,700$350/sqft |
Source: Realty Executives Northwest #L150185 Report a problem | ||
| 5/23/2014 | Listed for sale | $440,700$350/sqft |
Source: Realty Executives Northwest #L150185 Report a problem | ||
| 1/1/2014 | Listing removed | $440,700$350/sqft |
Source: Realty Executives Northwest #L147265 Report a problem | ||
| 8/23/2013 | Price change | $440,700-1.4%$350/sqft |
Source: Realty Executives Northwest #L147265 Report a problem | ||
| 5/3/2013 | Listed for sale | $447,000-0.2%$355/sqft |
Source: Realty Executives Northwest LLC #L145906 Report a problem | ||
| 1/1/2013 | Listing removed | $447,700$356/sqft |
Source: Realty Executives Northwest #L142981 Report a problem | ||
| 6/19/2012 | Listed for sale | $447,700$356/sqft |
Source: Realty Executives Northwest LLC #L142981 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,577 +10.5% | $362,600 |
| 2024 | $9,569 | $362,600 |
| 2023 | $9,569 +21% | $362,600 +53.8% |
| 2022 | $7,907 | $235,760 |
| 2021 | $7,907 | $235,760 |
| 2020 | $7,907 | $235,760 |
| 2019 | $7,907 | $235,760 |
| 2018 | $7,907 +8.9% | $235,760 +8.9% |
| 2017 | $7,261 | $216,480 |
| 2016 | $7,261 +2.6% | $216,480 |
| 2015 | $7,079 +2.5% | $216,480 |
| 2014 | $6,908 +2.3% | $216,480 |
| 2013 | $6,754 -3% | $216,480 -21% |
| 2012 | $6,965 | $273,880 |
| 2011 | $6,965 | $273,880 |
| 2010 | $6,965 +3.1% | $273,880 |
| 2009 | $6,757 | $273,880 |
| 2008 | $6,757 +18% | $273,880 +63.9% |
| 2007 | $5,726 +2.8% | $167,090 |
| 2006 | $5,571 +1.1% | $167,090 |
| 2005 | $5,511 +9.5% | $167,090 |
| 2003 | $5,033 +52.7% | $167,090 +39.7% |
| 1995 | $3,296 | $119,610 |
Find assessor info on the county website
Neighborhood: 06098
Nearby schools
GreatSchools rating
- NABatcheller Early Education CenterGrades: PK-2Distance: 0.6 mi
- NAPearson AcademyGrades: Distance: 1 mi
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 1 mi
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$693,500
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+$13,870
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$707,370
- Connecticut
- Litchfield County
- Winsted
- 06098
- 156 Shore Drive
Nearby cities
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