Wake up to sparkling water views and savor the serenity of lakefront living in this storybook Cape Cod-style retreat on Highland Lake's desirable east side. Tucked away on a peaceful private lane, this year-round haven offers 3 bedrooms & 2 full baths, perfectly blending classic charm with modern comfort. Step into the spacious kitchen, where sun-drenched mornings begin at the breakfast nook and flow effortlessly into a welcoming dining room-- ideal for holiday feasts & weekend gatherings. The bright, open main living area, with a wall of sliders, invites you to soak in sweeping water views and step out onto the expansive composite deck. With a retractable awning overhead, this outdoor oasis becomes your favorite spot for coffee at sunrise or cocktails at sunset. On cooler days, curl up by the wood-burning fireplace in the cozy family room, or use the space as a quiet, inspiring home office with views of the lake. Upstairs, three inviting bedrooms offer comfort and privacy for family and guests. Spend evenings making memories around the fire pit, watching the sun dip below the horizon. Launch your kayak from the private dock, take the boat out for a day of fun, or simply float & relax in the crystal-clear waters Highland Lake is known for. Recent updates include new roof (2025), new furnace (2021), vinyl siding + replacement windows. Additional features: 1-car attached garage, 1st floor laundry, walk-out basement, public water & sewer, keyless entry & convenient storage shed. Located just minutes from Route 8 with easy access to New York and the Berkshires, this home is more than a place-- it's a lifestyle. Don't just live near the lake...live the lake life you've always dreamed of! Professional interior photos coming soon...
Sold for $800,000
$800,000
266 Perch Rock Trail, Winchester, CT 06098
3beds
1,488sqft
Single Family Residence
Built in 1928
6,534 Square Feet Lot
$835,700 Zestimate®
$538/sqft
$2,652 Estimated rent
Home value
$835,700
Estimated sales range
Not available
$2,652/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Laurie C. Murray 860-212-8305,
KW Legacy Partners 860-313-0700
Bought with:
Annie Simard, RES.0822960
LPT Realty
Source: Smart MLS,MLS#: 24107321
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 160 Square Feet
- Dimensions: 10 x 16
Bedroom
- Features: Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 180 Square Feet
- Dimensions: 10 x 18
Bedroom
- Features: Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 162 Square Feet
- Dimensions: 9 x 18
Bathroom
- Features: Tub w/Shower
- Level: Main
Bathroom
- Features: Stall Shower
- Level: Main
Dining room
- Features: Ceiling Fan(s), Hardwood Floor
- Level: Main
- Area: 135 Square Feet
- Dimensions: 9 x 15
Family room
- Features: Ceiling Fan(s), Fireplace, Hardwood Floor
- Level: Main
- Area: 136 Square Feet
- Dimensions: 8 x 17
Kitchen
- Features: Dining Area, Hardwood Floor
- Level: Main
- Area: 140 Square Feet
- Dimensions: 10 x 14
Living room
- Features: Balcony/Deck, Sliders, Hardwood Floor
- Level: Main
- Area: 220 Square Feet
- Dimensions: 10 x 22
Heating
- Steam, Oil
Cooling
- Ceiling Fan(s), Window Unit(s)
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level
Features
- Doors: Storm Door(s)
- Windows: Storm Window(s)
- Basement: Full,Concrete
- Attic: Crawl Space,Access Via Hatch
- Number of fireplaces: 1
Interior area
- Total structure area: 1,488
- Total interior livable area: 1,488 sqft
- Finished area above ground: 1,488
Property
Parking
- Total spaces: 2
- Parking features: Attached, Off Street, Driveway, Asphalt
- Attached garage spaces: 1
- Has uncovered spaces: Yes
Features
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Lake, Walk to Water, Dock or Mooring
Lot
- Size: 6,534 sqft
- Features: Dry, Level
Details
- Parcel number: 924670
- Zoning: HL
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1928
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available
Green energy
- Energy efficient items: Thermostat, Doors, Windows
Community & neighborhood
Community
- Community features: Lake, Library, Medical Facilities, Public Rec Facilities
Location
- Region: Winsted
Price history
| Date | Event | Price |
|---|---|---|
| 8/4/2025 | Sold | $800,000+6.7%$538/sqft |
Source:  Smart MLS #24107321 Report a problem | ||
| 7/4/2025 | Pending sale | $750,000$504/sqft |
Source: Smart MLS #24107321 Report a problem | ||
| 7/3/2025 | Listed for sale | $750,000+74.4%$504/sqft |
Source: Smart MLS #24107321 Report a problem | ||
| 5/24/2019 | Sold | $430,000-1.1%$289/sqft |
Source: Smart MLS #170134003 Report a problem | ||
| 5/2/2019 | Pending sale | $434,900$292/sqft |
Source: Real Living Wareck D'Ostilio #170134003 Report a problem | ||
| 4/10/2019 | Price change | $434,900-3.3%$292/sqft |
Source: Real Living Wareck D'Ostilio #170134003 Report a problem | ||
| 12/17/2018 | Price change | $449,900-2.2%$302/sqft |
Source: Real Living Wareck D'Ostilio #170134003 Report a problem | ||
| 10/22/2018 | Listed for sale | $459,900+45.6%$309/sqft |
Source: Real Living Wareck D'Ostilio #170134003 Report a problem | ||
| 6/30/2015 | Listing removed | $1,300$1/sqft |
Source: The D'Amore Agency, LLC #L10010712 Report a problem | ||
| 12/17/2014 | Listed for rent | $1,300$1/sqft |
Source: The D'Amore Agency, LLC #L10010712 Report a problem | ||
| 12/30/2010 | Sold | $315,800-20%$212/sqft |
Source: Smart MLS #L136999 Report a problem | ||
| 9/14/2010 | Price change | $394,900-8.1%$265/sqft |
Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem | ||
| 7/24/2010 | Price change | $429,900-6.5%$289/sqft |
Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem | ||
| 4/7/2010 | Price change | $459,900-8%$309/sqft |
Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem | ||
| 8/31/2009 | Price change | $499,900-9.1%$336/sqft |
Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem | ||
| 5/25/2009 | Listed for sale | $549,900+511%$370/sqft |
Source: Listhub #L128580 Report a problem | ||
| 2/9/1996 | Sold | $90,000$60/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $11,678 +10.5% | $400,330 |
| 2024 | $10,565 | $400,330 |
| 2023 | $10,565 +21.9% | $400,330 +54.9% |
| 2022 | $8,668 | $258,440 |
| 2021 | $8,668 | $258,440 |
| 2020 | $8,668 | $258,440 |
| 2019 | $8,668 +1.4% | $258,440 +1.4% |
| 2018 | $8,546 +9% | $254,800 +9% |
| 2017 | $7,842 | $233,800 |
| 2016 | $7,842 +2.6% | $233,800 |
| 2015 | $7,645 +2.5% | $233,800 |
| 2014 | $7,461 +3.3% | $233,800 +1% |
| 2013 | $7,225 -2.5% | $231,560 -20.6% |
| 2012 | $7,412 | $291,480 |
| 2011 | $7,412 | $291,480 |
| 2010 | $7,412 +3.1% | $291,480 |
| 2009 | $7,191 | $291,480 |
| 2008 | $7,191 +14.4% | $291,480 +58.9% |
| 2007 | $6,288 +2.8% | $183,470 |
| 2006 | $6,117 +1.1% | $183,470 |
| 2005 | $6,051 +9.5% | $183,470 |
| 2003 | $5,526 | $183,470 |
Find assessor info on the county website
Neighborhood: 06098
Nearby schools
GreatSchools rating
- NABatcheller Early Education CenterGrades: PK-2Distance: 0.9 mi
- NAPearson AcademyGrades: Distance: 1.4 mi
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 1.4 mi
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- Connecticut
- Litchfield County
- Winsted
- 06098
- 266 Perch Rock Trail
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