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Sold for $925,000
  • $925,000

    258 Perch Rock Trail, Winchester, CT 06098

    4beds
    1,373sqft
    Single Family Residence
    Built in 1922
    6,534 Square Feet Lot
    $925,500 Zestimate®
    $674/sqft
    $2,571 Estimated rent

    Home value

    $925,500

    $851,000 - $1.01M

    $2,571/mo

    Zestimate® history
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    What's special

    Turn-key direct waterfront gem on Highland Lake! Perfectly positioned on the desirable east side of the lake, this beautifully maintained Cape offers abundant sunshine, gorgeous sunsets, & stunning water views. The updated kitchen features a breakfast bar, generous cabinet space, & opens to the dining room & inviting great room with hardwood floors & a gas fireplace. Enjoy lake views from the enclosed sunroom with sliders to the spacious deck, overlooking the level yard & private dock. The first floor offers a possible bedroom or office, full bath, and laundry. Upstairs are four additional bedrooms, including a beautiful lake facing primary bedroom with a large bay window, & breathtaking views. A full bath is conveniently located in the hall serving the upper level. Additional highlights include central air, whole-house generator, town water and sewer, newer roof, a full basement for storage & a putting green! Live like you are on vacation every day-swimming, boating, relaxing, and making memories with family and friends. This fabulous location offers quick access to Routes 8 & 44, with nearby attractions including Ski Sundown, Warner Theatre, wineries, breweries, hiking, and biking trails. Approx. 40 minutes to Hartford and Bradley International Airport, with convenient access toward New Haven and New York. Don't miss this rare opportunity to own your own slice of paradise on Highland Lake! Nestled in the foothills of the Berkshires in Northwest Connecticut, and set along the shores of Highland Lake, this property offers an exceptional four-season lifestyle in a truly scenic setting. One of Connecticut's premier full-recreation lakes, Highland Lake spans approximately 3 miles and over 440 acres, ideal for boating, kayaking, paddle boarding, swimming, and excellent fishing, including trout. In the winter months, the lake transforms into a classic New England destination for ice fishing, skating, snowmobiling, and cross-country skiing-bringing year-round enjoyment right outside your door. Located in the charming town of Winchester, you'll enjoy nearby dining, shops, and cafes in downtown Winsted, along with easy access to the renowned restaurants, boutique shopping, and timeless New England charm of Litchfield. Outdoor enthusiasts will appreciate close proximity to Ski Sundown and Butternut Ski Area for skiing, as well as local breweries including Little Red Barn Brewers and Norbrook Farm Brewery. Conveniently located with easy access to Routes 8 and 44, commuting is simple-approximately 40 minutes to Hartford and Bradley International Airport, with easy access to New Haven and New York City. Whether you're seeking a year-round residence or a weekend escape, this location offers the perfect balance of relaxation, recreation, and accessibility

    Zillow last checked:

    Listing updated:

    Listed by:

    Nancy B. Reardon (860)836-7506,

    Berkshire Hathaway NE Prop. 860-653-4507

    Bought with:

    Joan M. Muller, RES.0750075

    Berkshire Hathaway NE Prop.

    Source: Smart MLS,MLS#: 24171657MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 2
    • Full bathrooms: 2
    Primary bedroom
    • Features: Bay/Bow Window, Vaulted Ceiling(s), Wall/Wall Carpet
    • Level: Upper
    • Area: 144 Square Feet
    • Dimensions: 9 x 16
    Bedroom
    • Features: Vaulted Ceiling(s), Wall/Wall Carpet
    • Level: Upper
    Bedroom
    • Features: Vaulted Ceiling(s), Wall/Wall Carpet
    • Level: Upper
    Bedroom
    • Features: Vaulted Ceiling(s), Wall/Wall Carpet
    • Level: Upper
    Bathroom
    • Features: Tub w/Shower
    • Level: Main
    Bathroom
    • Features: Stall Shower
    • Level: Upper
    Dining room
    • Features: Combination Liv/Din Rm, Hardwood Floor
    • Level: Main
    • Area: 120 Square Feet
    • Dimensions: 10 x 12
    Kitchen
    • Features: Vaulted Ceiling(s), Breakfast Bar, Hardwood Floor
    • Level: Main
    • Area: 221 Square Feet
    • Dimensions: 13 x 17
    Living room
    • Features: Ceiling Fan(s), Combination Liv/Din Rm, Gas Log Fireplace, Sliders, Hardwood Floor
    • Level: Main
    • Area: 156 Square Feet
    • Dimensions: 12 x 13
    Office
    • Level: Main
    • Area: 120 Square Feet
    • Dimensions: 10 x 12
    Sun room
    • Features: Ceiling Fan(s), Sliders
    • Level: Main
    • Area: 207 Square Feet
    • Dimensions: 9 x 23
    Heating
    • Forced Air, Oil
    Cooling
    • Central Air
    Appliances
    • Included: Oven/Range, Range Hood, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Electric Water Heater
    • Laundry: Main Level
    Features
    • Open Floorplan
    • Basement: Partial
    • Attic: None
    • Number of fireplaces: 1
    Interior area
    • Total structure area: 1,373
    • Total interior livable area: 1,373 sqft
    • Finished area above ground: 1,373

    Property

    Features
    • Patio & porch: Enclosed, Porch, Deck
    • Exterior features: Rain Gutters, Stone Wall
    • Has view: Yes
    • View description: Water
    • Has water view: Yes
    • Water view: Water
    • Waterfront features: Waterfront, Lake
    Lot
    • Size: 6,534 sqft
    Details
    • Parcel number: 928340
    • Zoning: HLD
    • Other equipment: Generator

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Cape Cod
    • Property subtype: Single Family Residence
    Materials
    • Vinyl Siding
    • Foundation: Block, Concrete Perimeter
    • Roof: Asphalt
    Condition
    • New construction: No
    • Year built: 1922

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: Cable Available

    Community & neighborhood

    Location
    • Region: Winsted

    Price history

    DateEventPrice
    6/4/2026Sold$925,000+16.4%$674/sqft
    Source: Smart MLS #24171657 Report a problem
    5/12/2026Pending sale$795,000$579/sqft
    Source: Smart MLS #24171657 Report a problem
    5/7/2026Listed for sale$795,000+20.5%$579/sqft
    Source: Smart MLS #24171657 Report a problem
    7/30/2021Sold$660,000-5.6%$481/sqft
    Source: Smart MLS #170401997 Report a problem
    7/2/2021Contingent$699,000$509/sqft
    Source: Smart MLS #170401997 Report a problem
    6/19/2021Price change$699,000-4.9%$509/sqft
    Source: Smart MLS #170401997 Report a problem
    5/30/2021Listed for sale$735,000+40%$535/sqft
    Source: Smart MLS #170401997 Report a problem
    6/30/2016Listing removed$525,000$382/sqft
    Source: William Pitt Sotheby's International Realty #L10104089 Report a problem
    3/11/2016Price change$525,000+1.2%$382/sqft
    Source: William Pitt and Julia B. Fee Sotheby's International Realty #L10104089 Report a problem
    2/17/2016Listed for sale$519,000-2.1%$378/sqft
    Source: William Pitt and Julia B. Fee Sotheby's International Realty #L10104089 Report a problem
    10/1/2015Listing removed$529,900$386/sqft
    Source: William Pitt Sotheby's Int'l Realty #L149375 Report a problem
    6/10/2015Price change$529,900-3.6%$386/sqft
    Source: William Pitt and Julia B. Fee Sotheby's International Realty #L149375 Report a problem
    5/29/2015Price change$549,900-1.6%$401/sqft
    Source: William Pitt and Julia B. Fee Sotheby's International Realty #L149375 Report a problem
    3/26/2015Price change$559,000-0.2%$407/sqft
    Source: William Pitt Sotheby's International Realty #L149375 Report a problem
    2/1/2015Listed for sale$559,900$408/sqft
    Source: William Pitt Sotheby's Int'l Realty #L149375 Report a problem
    12/17/2014Listing removed$559,900$408/sqft
    Source: William Pitt Sotheby's Int'l Realty #L149375 Report a problem
    10/1/2014Price change$559,900+0.2%$408/sqft
    Source: William Pitt Sotheby's Int'l Realty #L149375 Report a problem
    8/16/2014Price change$559,000-2.8%$407/sqft
    Source: William Pitt Sotheby's International Realty #L149375 Report a problem
    7/17/2014Price change$575,000-2.5%$419/sqft
    Source: William Pitt Sotheby's International Realty #L149375 Report a problem
    6/25/2014Price change$589,900-4.7%$430/sqft
    Source: William Pitt Sotheby's International Realty #L149375 Report a problem
    4/8/2014Listed for sale$619,000$451/sqft
    Source: Litchfield Hills Sotheby's International Realty #L149375 Report a problem
    10/2/2013Listing removed$619,000$451/sqft
    Source: Litchfield Hills Sotheby's International Realty #l144018 Report a problem
    8/2/2013Price change$619,000-2.9%$451/sqft
    Source: Litchfield Hills Sotheby's International Realty #l144018 Report a problem
    10/4/2012Listed for sale$637,500+22.6%$464/sqft
    Source: Litchfield Hills Sotheby's International Realty #L144018 Report a problem
    10/4/2012Listing removed$1,000$1/sqft
    Source: Litchfield Hills Sotheby's International Realty #L143183 Report a problem
    7/9/2012Listed for rent$1,000$1/sqft
    Source: Litchfield Hills Sotheby's International Realty #L143183 Report a problem
    5/5/2007Sold$520,000$379/sqft
    Source: Smart MLS #G431090 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$12,680 +12%$434,700 +1.3%
    2024$11,324 $429,100
    2023$11,324 +26%$429,100 +60.1%
    2022$8,990 +0.4%$268,030 +0.4%
    2021$8,955 $266,980
    2020$8,955 $266,980
    2019$8,955 $266,980
    2018$8,955 +9.4%$266,980 +9.4%
    2017$8,182 +0.5%$243,950 +0.5%
    2016$8,145 +2.6%$242,830
    2015$7,941 +2.5%$242,830
    2014$7,749 +2.3%$242,830
    2013$7,576 +1.9%$242,830 -16.9%
    2012$7,432 $292,250
    2011$7,432 $292,250
    2010$7,432 +3.1%$292,250
    2009$7,210 $292,250
    2008$7,210 +15.7%$292,250 +60.7%
    2007$6,232 +2.8%$181,860
    2006$6,063 +1.1%$181,860
    2005$5,998 +9.5%$181,860
    2003$5,478 +54.6%$181,860 +41.4%
    1995$3,543 $128,570

    Find assessor info on the county website

    Neighborhood: 06098

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