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  • Listed by: Elevations Real Estate • Nathan Mastroeni • 802-289-8463
    $559,000

    303 Winding Way, Killington, VT 05751

    4beds
    1,776sqft
    : 
    $4,763/mo
    Get pre-qualified
    Single Family Residence
    Built in 1970
    1.23 Acres Lot
    $-- Zestimate®
    $315/sqft
    $-- HOA

    What's special

    New heating systemNew staircaseNew kitchen cabinetsUpdated with fresh paint
    Live where the Green Mountains are your backyard. This 4-bedroom chalet-style home sits on 1.23 acres in Killington, close to some of the best four-season recreation in the East. In winter, when the leaves drop, you get mountain views through the trees. Killington Resort, the largest ski area in the East, is a short drive away, with seven peaks, hundreds of acres of terrain, and a ski season that often starts in October and runs well into spring. Pico Mountain is also close, a favorite for its old-school Vermont feel, family-friendly trails, and smaller crowds. When the snow melts, the area turns to mountain biking, hiking, golf, and fishing. The Green Mountain National Forest is nearby, with miles of trails for hiking, snowshoeing, cross-country skiing, and snowmobiling. The Long Trail and Appalachian Trail cross Route 4 at Sherburne Pass, giving you easy access to day hikes with big views. Kent Pond, Gifford Woods State Park, and the Ottauquechee River are close for paddling, swimming, and fall foliage. After a day outside, Killington’s restaurants, breweries, and après-ski spots are close, and Rutland is an easy drive for groceries, dining, and shopping. Woodstock, Okemo, and Quechee are all within a day trip. The home has been updated with fresh paint, a new staircase, new kitchen cabinets, and a new heating system, so you can spend your time enjoying the area. It’s a good fit as a full-time home, a ski-season getaway, or a rental.
    17 hours
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    Zillow last checked:

    Listing updated:

    Listed by:

    Nathan Mastroeni,

    Elevations Real Estate 802-289-8463

    Source: PrimeMLS,MLS#: 5115977MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 3/4 bathrooms: 1
      Heating
      • Propane, Baseboard
      Cooling
      • None
      Appliances
      • Included: Dryer, Microwave, Refrigerator, Washer, Gas Stove
      Features
      • Natural Light
      • Flooring: Carpet
      • Has basement: No
      Interior area
      • Total structure area: 1,776
      • Total interior livable area: 1,776 sqft
      • Finished area above ground: 1,776
      • Finished area below ground: 0
      Video & virtual tour

      Property

      Parking
      • Parking features: Gravel
      Features
      • Levels: Two
      • Stories: 2
      • Exterior features: Deck
      • Has spa: Yes
      • Spa features: Heated
      • Has view: Yes
      • View description: Mountain(s)
      Lot
      • Size: 1.23 Acres
      • Features: Sloped
      Details
      • Parcel number: 58818510199
      • Zoning description: residential
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Chalet
      • Property subtype: Single Family Residence
      Materials
      • Other
      • Foundation: Block
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1970

      Utilities & green energy

      • Electric: Circuit Breakers
      • Sewer: Septic Tank
      • Utilities for property: Other

      Community & HOA

      Location
      • Region: Killington

      Financial & listing details

      • Price per square foot: $315/sqft
      • Tax assessed value: $222,090
      • Annual tax amount: $5,886
      • Date on market: 10/28/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $2,571/mo

        Price history

        DateEventPrice
        10/28/2026Listed for sale$559,000+2.8%$315/sqft
        Source: PrimeMLS #5115977 Report a problem
        10/23/2026Listing removed--
        Source: Owner Report a problem
        10/21/2026Price change$544,000-8.6%$306/sqft
        Source: Owner Report a problem
        10/16/2026Listed for sale$595,000+2.6%$335/sqft
        Source: Owner Report a problem
        10/14/2026Listing removed$579,900$327/sqft
        Source: PrimeMLS #5089932 Report a problem
        10/12/2026Pending sale$579,900$327/sqft
        Source: PrimeMLS #5089932 Report a problem
        10/5/2026Price change$579,900-1.7%$327/sqft
        Source: PrimeMLS #5089932 Report a problem
        9/28/2026Price change$589,900-1.7%$332/sqft
        Source: PrimeMLS #5089932 Report a problem
        9/23/2026Price change$599,900-2.6%$338/sqft
        Source: PrimeMLS #5089932 Report a problem
        9/2/2026Price change$615,900-1.4%$347/sqft
        Source: PrimeMLS #5089932 Report a problem
        8/27/2026Price change$624,900-3.8%$352/sqft
        Source: PrimeMLS #5089932 Report a problem
        8/12/2026Price change$649,500+3.3%$366/sqft
        Source: PrimeMLS #5089932 Report a problem
        7/9/2026Price change$629,000+14.4%$354/sqft
        Source: PrimeMLS #5089932 Report a problem
        6/17/2026Price change$549,900-1.8%$310/sqft
        Source: PrimeMLS #5089932 Report a problem
        5/30/2026Listed for sale$559,900$315/sqft
        Source: PrimeMLS #5089932 Report a problem
        5/30/2026Pending sale$559,900$315/sqft
        Source: PrimeMLS #5089932 Report a problem
        5/20/2026Listed for sale$559,900-1.6%$315/sqft
        Source: PrimeMLS #5089932 Report a problem
        5/15/2026Listing removed$569,000$320/sqft
        Source: PrimeMLS #5073999 Report a problem
        5/6/2026Price change$569,000-0.9%$320/sqft
        Source: PrimeMLS #5073999 Report a problem
        4/25/2026Price change$574,000-0.9%$323/sqft
        Source: PrimeMLS #5073999 Report a problem
        4/6/2026Price change$579,000-3.3%$326/sqft
        Source: PrimeMLS #5073999 Report a problem
        1/15/2026Price change$599,000+5.1%$337/sqft
        Source: PrimeMLS #5073999 Report a problem
        12/14/2025Price change$569,900+11.8%$321/sqft
        Source: Owner Report a problem
        12/8/2025Pending sale$509,900$287/sqft
        Source: Owner Report a problem
        12/7/2025Listed for sale$509,900+50%$287/sqft
        Source: Owner Report a problem
        12/24/2024Sold$340,000$191/sqft
        Source: PrimeMLS #5023127 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024-- $222,090
        2023-- $222,090
        2022-- $222,090
        2021-- $222,090
        2020-- $222,090
        2019-- $222,090
        2018-- $222,090
        2017-- $222,090
        2016-- $222,090 +9904.1%
        2015-- $2,220
        2014-- $2,220
        2013-- $2,220 0%
        2012-- $2,221
        2011-- $2,221 +26.9%
        2010-- $1,750
        2009-- $1,750
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 05751

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