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Under contract
    • $799,900

    119 Cheifton Pl, Winchester, VA 22602

    4beds
    4,160sqft
    : 
    $4,972/mo
    Get pre-qualified
    Single Family Residence
    Built in 2005
    2.14 Acres Lot
    $796,100 Zestimate®
    $192/sqft
    $-- HOA

    What's special

    Cozy stone fireplaceHuge recreation roomSweeping countryside viewsLush landscapingWide drivewayFrame-worthy curb appealBright breakfast nook
    Boasting timeless architectural charm and sweeping countryside views, 119 Cheifton Place offers an extraordinary lifestyle on an expansive two plus acre lot. Frame-worthy curb appeal greets you with lush landscaping, tall shade trees, and a welcoming covered porch, while a wide driveway and attached three-car garage comfortably accommodate all your guests. Inside, an inviting foyer detailed with refined pillars, custom crown molding, and wainscoting sets a sophisticated tone. Host formal dinners in the dedicated dining room, or work in peace behind the glass French doors of the private main-floor office. The expansive family room anchors the main floor with its high vaulted ceilings, cozy stone fireplace, and abundant natural light pouring in through large picture windows. Nearby, the well-appointed kitchen features timeless cherry cabinetry, a center island, stainless steel appliances, and a bright breakfast nook. A flexible den just off the kitchen boasts vaulted ceilings and tons of windows showcasing beautiful views, offering endless possibilities as a playroom, library, or secondary sitting room. A main-level powder room and a spacious laundry room with built-in storage complete this thoughtfully designed main living area. The main-level primary suite serves as a serene retreat, complete with expansive windows, two fabulous walk-in closets, and a spa-like ensuite bath featuring double sinks, a deep soaking tub, and a separate walk-in shower. Two additional generously sized bedrooms and another full bath round out the main floor. Downstairs, the finished walkout basement exponentially expands your living options, flooded with natural light from large windows. This thoughtfully finished lower level offers unprecedented flexibility, featuring a huge recreation room, a media room tailored for movie nights or game days, a bright work space, a private guest bedroom, a third full bath, and an unfinished area perfect for storage. Whether you imagine an in-law suite, a high-end game room, a home gym, or the ultimate entertainment hub, this versatile space delivers endless possibilities. Designed for seamless indoor-outdoor entertaining, the exterior is a private oasis framed by meticulous landscaping. Relax on the rear deck while taking in breathtaking panoramic views of the lush rolling countryside, gather for crisp autumn evenings around the fire pit on the lower brick patio, or unwind in the shade on the covered patio directly off the basement walkout. Impeccably maintained inside and out, this remarkable property is a rare find offering unmatched space, classic design, and resort-style living in a prime location minutes to agritourism, downtown Winchester, schools, shopping and more.
    20 days
    930
    65

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Dan Whitacre 540-327-6718,

    Colony Realty 540-662-0323

    Source: Bright MLS,MLS#: VAFV2045098MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      • Main level bathrooms: 3
      • Main level bedrooms: 3
      Rooms
      • Room types: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Den, Laundry, Office, Recreation Room, Storage Room, Media Room, Bonus Room, Primary Bathroom, Full Bath, Half Bath
      Primary bedroom
      • Features: Attached Bathroom, Ceiling Fan(s), Flooring - Carpet, Walk-In Closet(s)
      • Level: Main
      Bedroom 2
      • Features: Ceiling Fan(s), Flooring - Carpet
      • Level: Main
      Bedroom 3
      • Features: Ceiling Fan(s), Flooring - Carpet
      • Level: Main
      Bedroom 4
      • Features: Flooring - Carpet, Walk-In Closet(s)
      • Level: Lower
      Primary bathroom
      • Features: Bathroom - Walk-In Shower, Soaking Tub, Double Sink, Flooring - Ceramic Tile
      • Level: Main
      Bonus room
      • Features: Flooring - Carpet
      • Level: Lower
      Den
      • Features: Cathedral/Vaulted Ceiling, Ceiling Fan(s), Flooring - HardWood
      • Level: Main
      Dining room
      • Features: Flooring - HardWood, Formal Dining Room, Crown Molding
      • Level: Main
      Family room
      • Features: Cathedral/Vaulted Ceiling, Flooring - HardWood, Ceiling Fan(s), Fireplace - Gas
      • Level: Main
      Other
      • Features: Bathroom - Tub Shower
      • Level: Main
      Other
      • Features: Bathroom - Tub Shower
      • Level: Lower
      Half bath
      • Level: Main
      Kitchen
      • Features: Breakfast Nook, Dining Area, Flooring - Ceramic Tile, Kitchen Island, Eat-in Kitchen
      • Level: Main
      Laundry
      • Level: Main
      Media room
      • Features: Flooring - Carpet
      • Level: Lower
      Office
      • Features: Crown Molding, Flooring - HardWood
      • Level: Main
      Recreation room
      • Features: Flooring - Carpet
      • Level: Lower
      Storage room
      • Features: Basement - Unfinished
      • Level: Lower
      Heating
      • Forced Air, Propane
      Cooling
      • Central Air, Ceiling Fan(s), Electric
      Appliances
      • Included: Microwave, Cooktop, Dishwasher, Disposal, Dryer, Washer, Refrigerator, Oven, Stainless Steel Appliance(s), Water Heater
      • Laundry: Main Level, Laundry Room
      Features
      • Soaking Tub, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Ceiling Fan(s), Crown Molding, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Formal/Separate Dining Room, Eat-in Kitchen, Kitchen Island, Kitchen - Table Space, Primary Bath(s), Recessed Lighting, Wainscotting, Walk-In Closet(s), Vaulted Ceiling(s)
      • Flooring: Hardwood, Carpet, Ceramic Tile, Wood
      • Doors: French Doors
      • Windows: Window Treatments
      • Basement: Full,Interior Entry,Partially Finished,Exterior Entry,Connecting Stairway,Walk-Out Access,Windows
      • Number of fireplaces: 1
      • Fireplace features: Stone, Gas/Propane
      Interior area
      • Total structure area: 5,536
      • Total interior livable area: 4,160 sqft
      • Finished area above ground: 2,784
      • Finished area below ground: 1,376

      Property

      Parking
      • Total spaces: 3
      • Parking features: Garage Faces Front, Inside Entrance, Garage Door Opener, Attached, Driveway, Off Street
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: None
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Deck, Patio, Porch, Brick
      • Exterior features: Extensive Hardscape
      • Pool features: None
      • Has view: Yes
      • View description: Scenic Vista
      Lot
      • Size: 2.14 Acres
      • Features: Corner Lot, Landscaped
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: 621412
      • Zoning: RA
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch/Rambler
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding, Brick
      • Foundation: Concrete Perimeter
      Condition
      • New construction: No
      • Year built: 2005

      Utilities & green energy

      • Sewer: On Site Septic
      • Water: Well

      Community & HOA

      Community
      • Subdivision: The Orchard
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $192/sqft
      • Tax assessed value: $837,700
      • Annual tax amount: $4,169
      • Date on market: 9/30/2026
      • Listing agreement: Exclusive Right To Sell
      • Inclusions: Bose Speaker System & Uv Light System In Hvac
      • Ownership: Fee Simple

        Estimated market value

        $796,100

        $756,000 - $836,000

        $3,415/mo

        Price history

        DateEventPrice
        10/9/2026Contingent$799,900$192/sqft
        Source: Bright MLS #VAFV2045098 Report a problem
        9/30/2026Listed for sale$799,900+98.5%$192/sqft
        Source: Bright MLS #VAFV2045098 Report a problem
        1/25/2005Sold$403,000+374.1%$97/sqft
        Source: Agent Provided Report a problem
        7/29/2003Sold$85,000$20/sqft
        Source: Agent Provided Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$1,888 -46.2%$786,700 +14.3%
        2024$3,511 $688,400
        2023$3,511 +2.7%$688,400 +22.8%
        2022$3,419 $560,500
        2021-- $560,500 +13.3%
        2020$3,018 -50%$494,700
        2019$6,035 +110.5%$494,700 +5.2%
        2018$2,868 +1.7%$470,100
        2017$2,821 +10%$470,100 +10%
        2016$2,564 +7.1%$427,400
        2015$2,393 +108%$427,400 +9.5%
        2014$1,151 $390,300
        2013-- $390,300 -0.8%
        2012-- $393,400
        2011-- $393,400 -10.5%
        2010-- $439,400
        2009-- $439,400 -10.8%
        2008-- $492,700
        2007-- $492,700
        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.
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        Climate risks

        Neighborhood: 22602

        Getting around

        2 / 100
        Car-Dependent
        16 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Frederick County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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