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Under contract
    • $825,000

    356 Chimney Cir, Middletown, VA 22645

    6beds
    5,633sqft
    : 
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    Single Family Residence
    Built in 2005
    3.54 Acres Lot
    $814,600 Zestimate®
    $146/sqft
    $-- HOA

    What's special

    Additional storage roomFully finished lower levelHot tubSpacious main-level primary suitePrivate backyardSoaring ceilingsTwo private ensuite bedrooms
    Welcome to luxury living in the prestigious Chimney Hill Estates of Middletown! Perfectly positioned on just over 3.5 picturesque acres, this exceptional custom home offers more than 5,500 finished square feet of thoughtfully designed living space with room for every stage of life. The impressive main level welcomes you with soaring ceilings, abundant natural light, and a stunning two-story family room that serves as the heart of the home. The gourmet kitchen is a chef's dream, featuring a large center island, abundant cabinetry, and generous prep space, making it ideal for entertaining and everyday living. Retreat to the spacious main-level primary suite, complete with a luxurious ensuite bath designed for relaxation and comfort. Upstairs, you'll find four generously sized bedrooms and three full bathrooms, including two private ensuite bedrooms and two additional bedrooms connected by a convenient Jack-and-Jill bath, offering an ideal layout for family and guests. The fully finished lower level is a home all its own, featuring a complete in-law suite with a full kitchen, living room, family room, bedroom, game room, separate laundry room, and an additional storage room—perfect for multigenerational living, extended guests, or long-term accommodations. Step outside to enjoy the peaceful surroundings from the expansive rear deck, where a hot tub invites you to unwind while overlooking the private backyard. A storage shed equipped with solar panels adds valuable functionality and energy efficiency. Located in the highly desirable Chimney Hill Estates, this remarkable property offers the perfect blend of luxury, space, and privacy while remaining just minutes from historic Middletown, Winchester, shopping, dining, and major commuter routes. This is more than a home—it's a lifestyle. Schedule your private tour today and experience everything this extraordinary property has to offer.
    19 days
    |
    1,885
    |
    39
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Julie Teets 540-533-8293,

    ERA Oakcrest Realty, Inc.

    Source: Bright MLS,MLS#: VAFV2042954MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      • Main level bathrooms: 2
      • Main level bedrooms: 1
      Rooms
      • Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Game Room, Family Room, Breakfast Room, 2nd Stry Fam Rm, Laundry, Storage Room, Bedroom 6, Bathroom 2, Bathroom 3, Primary Bathroom, Full Bath, Half Bath
      Primary bedroom
      • Level: Main
      Bedroom 2
      • Level: Upper
      Bedroom 3
      • Level: Upper
      Bedroom 4
      • Level: Upper
      Bedroom 6
      • Level: Lower
      Primary bathroom
      • Level: Main
      Bathroom 2
      • Level: Upper
      Bathroom 3
      • Level: Upper
      Other
      • Level: Main
      Breakfast room
      • Level: Main
      Dining room
      • Level: Main
      Family room
      • Level: Lower
      Other
      • Level: Upper
      Other
      • Level: Lower
      Game room
      • Level: Lower
      Half bath
      • Level: Main
      Kitchen
      • Level: Lower
      Kitchen
      • Level: Main
      Laundry
      • Level: Lower
      Laundry
      • Level: Lower
      Laundry
      • Level: Main
      Living room
      • Level: Main
      Storage room
      • Level: Lower
      Heating
      • Forced Air, Propane
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Cooktop, Down Draft, Dishwasher, Disposal, Dryer, Ice Maker, Double Oven, Oven/Range - Electric, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater
      • Laundry: Laundry Room
      Features
      • 2nd Kitchen, Bathroom - Stall Shower, Bathroom - Tub Shower, Breakfast Area, Built-in Features, Chair Railings, Central Vacuum, Ceiling Fan(s), Crown Molding, Entry Level Bedroom, Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen Island, Pantry, Primary Bath(s), Upgraded Countertops, Walk-In Closet(s)
      • Flooring: Carpet, Wood
      • Basement: Full,Partially Finished,Partial
      • Number of fireplaces: 2
      • Fireplace features: Mantel(s), Gas/Propane
      Interior area
      • Total structure area: 5,808
      • Total interior livable area: 5,633 sqft
      • Finished area above ground: 3,515
      • Finished area below ground: 2,118

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Faces Side, Garage Door Opener, Inside Entrance, Attached, Driveway
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: None
      Features
      • Levels: Three
      • Stories: 3
      • Patio & porch: Deck, Patio
      • Pool features: None
      • Has spa: Yes
      • Spa features: Bath, Hot Tub
      Lot
      • Size: 3.54 Acres
      • Features: Backs to Trees, Front Yard, Rear Yard, SideYard(s)
      Details
      • Additional structures: Above Grade, Below Grade, Outbuilding
      • Parcel number: 833122
      • Zoning: RA
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Brick, Vinyl Siding
      • Foundation: Permanent
      Condition
      • Excellent
      • New construction: No
      • Year built: 2005

      Utilities & green energy

      • Sewer: Septic Exists
      • Water: Well

      Community & HOA

      Community
      • Subdivision: Chimney Hill Estates
      HOA
      • Has HOA: No
      Location
      • Region: Middletown

      Financial & listing details

      • Price per square foot: $146/sqft
      • Tax assessed value: $699,300
      • Annual tax amount: $3,357
      • Date on market: 6/25/2026
      • Listing agreement: Exclusive Right To Sell
      • Inclusions: Propane Tank
      • Ownership: Fee Simple

        Estimated market value

        $814,600

        $774,000 - $855,000

        $4,620/mo

        Price history

        DateEventPrice
        7/5/2026Contingent$825,000$146/sqft
        Source: Bright MLS #VAFV2042954 Report a problem
        6/25/2026Listed for sale$825,000$146/sqft
        Source: Bright MLS #VAFV2042954 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,357 +11.7%$699,300 +18.7%
        2024$3,005 $589,200
        2023$3,005 +104.2%$589,200 +22.1%
        2022$1,472 $482,500
        2021$1,472 -44.8%$482,500 +10.4%
        2020$2,665 -50%$436,900
        2019$5,330 +110.5%$436,900 +5.3%
        2018$2,532 +1.7%$415,100
        2017$2,491 +7.7%$415,100 +7.7%
        2016$2,312 +7.1%$385,400
        2015$2,158 +114%$385,400 +12.7%
        2014$1,009 $342,100
        2013-- $342,100 -0.8%
        2012-- $344,800
        2011-- $344,800 -17.9%
        2010-- $420,000
        2009-- $420,000 -4.2%
        2008-- $438,200
        2007-- $438,200
        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: 22645

        Getting around

        0 / 100
        Car-Dependent
        8 / 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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