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For sale
    • Price cut: $20K (4/23)
    $749,000

    121 West Wakefield Boulevard, Winchester, CT 06098

    4beds
    2,265sqft
    : 
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    Single Family Residence
    Built in 1996
    1 Acres Lot
    $-- Zestimate®
    $331/sqft
    $-- HOA

    What's special

    Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent major upgrades ensure worry free enjoyment, including a high-efficiency HVAC (2024), new roof (2022), new siding, exterior doors, added insulation, two remodeled baths, full interior paint, and newer carpet throughout. Extensive landscaping has been completed, including new front railings, leveling and removal of several large trees. Previously a successful Airbnb, this property offers abundant parking, a two-car garage, and dual laundry facilities. Embrace all seasons on Highland Lake - from summer boating and fishing, lake is stocked with trout and bass for fishing enthusiasts, to winter ice skating/fishing. Your lakeside dream awaits! All furniture and household items included. Ring camera is active on exterior. Additional Tax bill for private waterfront is $523 p/y
    101 days
    |
    1,476
    |
    59
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Elizabeth Stockwell (860)970-9615,

    Coldwell Banker Realty 860-674-0300

    Source: Smart MLS,MLS#: 24159801MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Full Bath, Interior Balcony, Sliders, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Dining room
      • Features: Bay/Bow Window
      • Level: Main
      Living room
      • Features: Balcony/Deck, Fireplace
      • Level: Main
      Other
      • Features: Wet Bar, Full Bath, Hardwood Floor
      • Level: Main
      Heating
      • Heat Pump, Forced Air, Electric, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Cooktop, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Upper Level
      Features
      • Doors: Storm Door(s)
      • Windows: Thermopane Windows
      • Basement: Full
      • Attic: Pull Down Stairs
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,265
      • Total interior livable area: 2,265 sqft
      • Finished area above ground: 2,265

      Property

      Parking
      • Total spaces: 2
      • Parking features: Detached
      • Garage spaces: 2
      Features
      • Exterior features: Balcony
      • On waterfront: Yes
      • Waterfront features: Waterfront, Lake
      Lot
      • Size: 1 Acres
      • Features: Rear Lot, Few Trees, Sloped
      Details
      • Parcel number: 2329656
      • Zoning: HLD

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1996

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      Green energy
      • Energy efficient items: Thermostat, Doors, Windows

      Community & HOA

      Community
      • Features: Near Public Transport
      HOA
      • Has HOA: No
      Location
      • Region: Winsted

      Financial & listing details

      • Price per square foot: $331/sqft
      • Tax assessed value: $352,170
      • Annual tax amount: $10,273
      • Date on market: 4/2/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        4/23/2026Price change$749,000-2.6%$331/sqft
        Source: Smart MLS #24159801 Report a problem
        4/9/2026Listed for sale$769,000+69%$340/sqft
        Source: Smart MLS #24159801 Report a problem
        2/3/2026Listing removed$4,000$2/sqft
        Source: Zillow Rentals Report a problem
        10/31/2025Price change$4,000-4.8%$2/sqft
        Source: Zillow Rentals Report a problem
        10/14/2025Listed for rent$4,200$2/sqft
        Source: Zillow Rentals Report a problem
        2/28/2022Sold$455,000-7.1%$201/sqft
        Source: Smart MLS #170457229 Report a problem
        2/25/2022Contingent$489,900$216/sqft
        Source: Smart MLS #170457229 Report a problem
        2/24/2022Pending sale$489,900$216/sqft
        Source: Berkshire Hathaway HomeServices New England Properties #170457229 Report a problem
        2/24/2022Listed for sale$489,900$216/sqft
        Source: Smart MLS #170457229 Report a problem
        2/11/2022Contingent$489,900$216/sqft
        Source: Smart MLS #170457229 Report a problem
        1/13/2022Pending sale$489,900$216/sqft
        Source: Berkshire Hathaway HomeServices New England Properties #170457229 Report a problem
        12/15/2021Listed for sale$489,900-3.8%$216/sqft
        Source: Smart MLS #170457229 Report a problem
        11/12/2021Listing removed--
        Source: Smart MLS #170399855 Report a problem
        8/31/2021Price change$509,000-7.3%$225/sqft
        Source: Smart MLS #170399855 Report a problem
        6/28/2021Price change$549,000-3.5%$242/sqft
        Source: Smart MLS #170399855 Report a problem
        5/26/2021Listed for sale$569,000+92.9%$251/sqft
        Source: Smart MLS #170399855 Report a problem
        8/1/2013Sold$295,000-48.7%$130/sqft
        Source: Smart MLS #G641840 Report a problem
        7/22/2004Sold$575,000$254/sqft
        Source: Smart MLS #L109490 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,273 +10.5%$352,170
        2024$9,294 $352,170
        2023$9,294 +4.4%$352,170 +32.6%
        2022$8,905 $265,510
        2021$8,905 $265,510
        2020$8,905 $265,510
        2019$8,905 $265,510
        2018$8,905 +0.8%$265,510 +0.8%
        2017$8,832 $263,340
        2016$8,832 +2.6%$263,340
        2015$8,611 +2.5%$263,340
        2014$8,403 +2.3%$263,340
        2013$8,216 -3.1%$263,340 -21%
        2012$8,475 $333,270
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 06098

        Getting around

        5 / 100
        Car-Dependent
        30 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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