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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
    $846,700 Zestimate®
    $538/sqft
    $2,333 Estimated rent

    Home value

    $846,700

    $720,000 - $999,000

    $2,333/mo

    Zestimate® history
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    What's special

    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...

    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#: 24107321MLS Logo

    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 Square Feet
    • 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 & HOA

    Community
    • Features: Lake, Library, Medical Facilities, Public Rec Facilities
    HOA
    • Has HOA: No
    Location
    • Region: Winsted

    Financial & listing details

    • Price per square foot: $538/sqft
    • Tax assessed value: $400,330
    • Annual tax amount: $11,678
    • Date on market: 6/28/2025

    Price history

    DateEventPrice
    8/4/2025Sold$800,000+6.7%$538/sqft
    Source: Smart MLS #24107321 Report a problem
    7/4/2025Pending sale$750,000$504/sqft
    Source: Smart MLS #24107321 Report a problem
    7/3/2025Listed for sale$750,000+74.4%$504/sqft
    Source: Smart MLS #24107321 Report a problem
    5/24/2019Sold$430,000-1.1%$289/sqft
    Source: Smart MLS #170134003 Report a problem
    5/2/2019Pending sale$434,900$292/sqft
    Source: Real Living Wareck D'Ostilio #170134003 Report a problem
    4/10/2019Price change$434,900-3.3%$292/sqft
    Source: Real Living Wareck D'Ostilio #170134003 Report a problem
    12/17/2018Price change$449,900-2.2%$302/sqft
    Source: Real Living Wareck D'Ostilio #170134003 Report a problem
    10/22/2018Listed for sale$459,900+45.6%$309/sqft
    Source: Real Living Wareck D'Ostilio #170134003 Report a problem
    6/30/2015Listing removed$1,300$1/sqft
    Source: The D'Amore Agency, LLC #L10010712 Report a problem
    12/17/2014Listed for rent$1,300$1/sqft
    Source: The D'Amore Agency, LLC #L10010712 Report a problem
    12/30/2010Sold$315,800-20%$212/sqft
    Source: Smart MLS #L136999 Report a problem
    9/14/2010Price change$394,900-8.1%$265/sqft
    Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem
    7/24/2010Price change$429,900-6.5%$289/sqft
    Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem
    4/7/2010Price change$459,900-8%$309/sqft
    Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem
    8/31/2009Price change$499,900-9.1%$336/sqft
    Source: REALTY EXECUTIVES NORTHWEST #L131700 Report a problem
    5/25/2009Listed for sale$549,900+511%$370/sqft
    Source: Listhub #L128580 Report a problem
    2/9/1996Sold$90,000$60/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax 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

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