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For sale
    • $824,900

    8999 Orchard Dr, Chestertown, MD 21620

    5beds
    4,353sqft
    : 
    $5,466/mo
    Get pre-qualified
    Single Family Residence
    Built in 2006
    2.23 Acres Lot
    $803,400 Zestimate®
    $190/sqft
    $-- HOA

    What's special

    Fully furnished screening roomBeautifully refreshed hall bathPrivate executive officeSleek updated fixturesSpacious walk-in closetPrivate ground-level entranceLarge walk-in shower
    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents
    13 days
    |
    1,087
    |
    68
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Terri Kulp 301-462-9976,

    Coldwell Banker Chesapeake Real Estate Company 410-778-0330

    Source: Bright MLS,MLS#: MDKE2006786MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 3
      • 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, Bedroom 5, Kitchen, Den, Foyer, Sun/Florida Room, In-Law/auPair/Suite, Laundry, Office, Storage Room, Media Room, Bathroom 1, Primary Bathroom, Half Bath
      Primary bedroom
      • Features: Flooring - Carpet, Walk-In Closet(s)
      • Level: Main
      • Area: 210 Square Feet
      • Dimensions: 15 X 14
      Bedroom 2
      • Features: Flooring - Carpet
      • Level: Upper
      • Area: 165 Square Feet
      • Dimensions: 15 X 11
      Bedroom 3
      • Features: Flooring - Carpet
      • Level: Upper
      • Area: 130 Square Feet
      • Dimensions: 13 X 10
      Bedroom 4
      • Features: Flooring - Carpet
      • Level: Upper
      • Area: 120 Square Feet
      • Dimensions: 10 X 12
      Bedroom 5
      • Features: Flooring - Carpet
      • Level: Upper
      • Area: 286 Square Feet
      • Dimensions: 22 X 13
      Primary bathroom
      • Features: Soaking Tub, Bathroom - Walk-In Shower, Countertop(s) - Quartz, Double Sink, Flooring - Luxury Vinyl Plank
      • Level: Main
      Bathroom 1
      • Features: Bathroom - Walk-In Shower
      • Level: Lower
      Den
      • Features: Flooring - Luxury Vinyl Plank
      • Level: Lower
      Dining room
      • Features: Flooring - HardWood
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 12 X 11
      Foyer
      • Features: Flooring - HardWood
      • Level: Main
      Half bath
      • Features: Flooring - HardWood
      • Level: Main
      Other
      • Features: Flooring - Luxury Vinyl Plank
      • Level: Lower
      Kitchen
      • Features: Granite Counters, Eat-in Kitchen, Kitchen - Propane Cooking, Flooring - Luxury Vinyl Plank, Built-in Features, Countertop(s) - Quartz, Double Sink, Kitchen Island, Pantry
      • Level: Main
      • Area: 352 Square Feet
      • Dimensions: 16 X 22
      Kitchen
      • Features: Flooring - Luxury Vinyl Plank, Kitchen - Electric Cooking
      • Level: Lower
      Laundry
      • Features: Flooring - Ceramic Tile
      • Level: Main
      Laundry
      • Level: Lower
      Living room
      • Features: Flooring - HardWood, Fireplace - Other, Cathedral/Vaulted Ceiling, Ceiling Fan(s)
      • Level: Main
      • Area: 154 Square Feet
      • Dimensions: 11 X 14
      Living room
      • Features: Flooring - Luxury Vinyl Plank, Living/Dining Room Combo
      • Level: Lower
      Media room
      • Features: Flooring - Carpet
      • Level: Lower
      Office
      • Features: Flooring - HardWood
      • Level: Main
      Storage room
      • Features: Flooring - Concrete
      • Level: Lower
      Other
      • Features: Balcony Access, Flooring - Luxury Vinyl Plank
      • Level: Main
      • Area: 252 Square Feet
      • Dimensions: 18 X 14
      Heating
      • Forced Air, Heat Pump, Zoned, Electric, Propane
      Cooling
      • Ceiling Fan(s), Central Air, Heat Pump, Electric
      Appliances
      • Included: Dryer, Double Oven, Refrigerator, Extra Refrigerator/Freezer, Range Hood, Stainless Steel Appliance(s), Washer, Cooktop, Dishwasher, Exhaust Fan, Microwave, Oven/Range - Gas, Oven/Range - Electric, Washer/Dryer Stacked, Tankless Water Heater, Water Conditioner - Owned, Water Treat System
      • Laundry: Dryer In Unit, Has Laundry, Main Level, Washer In Unit, Lower Level, Laundry Room
      Features
      • Kitchen Island, Kitchen - Table Space, Dining Area, Primary Bath(s), Ceiling Fan(s), Kitchen - Gourmet, Walk-In Closet(s), Wine Storage, 2nd Kitchen, Bathroom - Walk-In Shower, Built-in Features, Open Floorplan, Formal/Separate Dining Room, Cathedral Ceiling(s), Dry Wall
      • Flooring: Carpet, Ceramic Tile, Hardwood, Heated, Laminate, Wood
      • Doors: Sliding Glass
      • Windows: Double Pane Windows, Screens, Window Treatments
      • Basement: Connecting Stairway,Full,Heated,Improved,Exterior Entry,Partially Finished,Sump Pump,Walk-Out Access,Windows
      • Number of fireplaces: 1
      • Fireplace features: Glass Doors, Gas/Propane, Mantel(s)
      Interior area
      • Total structure area: 4,353
      • Total interior livable area: 4,353 sqft
      • Finished area above ground: 2,653
      • Finished area below ground: 1,700

      Property

      Parking
      • Total spaces: 6
      • Parking features: Garage Faces Side, Garage Door Opener, Inside Entrance, Asphalt, Off Street, Attached, Driveway
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      • Details: Garage Sqft: 552
      Accessibility
      • Accessibility features: Other Bath Mod, Roll-in Shower
      Features
      • Levels: Three
      • Stories: 3
      • Patio & porch: Porch, Patio
      • Exterior features: Lighting
      • Has private pool: Yes
      • Pool features: Heated, In Ground, Private
      • Fencing: Board,Partial,Back Yard,Wood
      Lot
      • Size: 2.23 Acres
      • Features: Landscaped, Front Yard, Poolside, Private, Rear Yard, Level, SideYard(s), Rural
      Details
      • Additional structures: Above Grade, Below Grade, Outbuilding
      • Parcel number: 1504023382
      • Zoning: RR
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Craftsman
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Brick/Mortar, Concrete Perimeter
      • Roof: Architectural Shingle
      Condition
      • Very Good
      • New construction: No
      • Year built: 2006
      Details
      • Builder name: DREAM HOME BUILDERS

      Utilities & green energy

      • Sewer: Private Septic Tank
      • Water: Well
      • Utilities for property: Cable Available, Electricity Available, Phone Available, Propane, Fiber Optic, Broadband

      Community & HOA

      Community
      • Subdivision: Orchard Hill
      HOA
      • Has HOA: No
      Location
      • Region: Chestertown

      Financial & listing details

      • Price per square foot: $190/sqft
      • Tax assessed value: $623,867
      • Annual tax amount: $6,813
      • Date on market: 7/25/2026
      • Listing agreement: Exclusive Right To Sell
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Road surface type: Black Top

        Estimated market value

        $803,400

        $763,000 - $844,000

        $4,894/mo

        Price history

        DateEventPrice
        7/25/2026Listed for sale$824,900+32%$190/sqft
        Source: Bright MLS #MDKE2006786 Report a problem
        6/13/2022Sold$625,000$144/sqft
        Source: Bright MLS #MDKE2001336 Report a problem
        5/27/2022Pending sale$625,000$144/sqft
        Source: Bright MLS #MDKE2001336 Report a problem
        4/21/2022Contingent$625,000$144/sqft
        Source: Bright MLS #MDKE2001336 Report a problem
        4/21/2022Listed for sale$625,000+86.6%$144/sqft
        Source: Bright MLS #MDKE2001336 Report a problem
        1/7/2011Sold$335,000-21.2%$77/sqft
        Source: Public Record Report a problem
        7/5/2009Listing removed$424,900$98/sqft
        Source: NRT MidAtlantic #KE6974409 Report a problem
        5/16/2009Price change$424,900-4.5%$98/sqft
        Source: NRT MidAtlantic #KE6974409 Report a problem
        4/9/2009Price change$444,900-3.1%$102/sqft
        Source: NRT MidAtlantic #KE6974409 Report a problem
        3/21/2009Price change$459,000-4.2%$105/sqft
        Source: NRT MidAtlantic #KE6974409 Report a problem
        2/5/2009Listed for sale$479,000-2%$110/sqft
        Source: NRT MidAtlantic #KE6974409 Report a problem
        12/15/2008Listing removed$489,000$112/sqft
        Source: NRT MidAtlantic #KE6912414 Report a problem
        11/2/2008Listed for sale$489,000+475.3%$112/sqft
        Source: NRT MidAtlantic #KE6912414 Report a problem
        5/23/2003Sold$85,000$20/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,051 +55.8%$600,800 +17.3%
        2024$5,809 +20.9%$512,267 +20.9%
        2023$4,805 +27.5%$423,733 +26.4%
        2022$3,768 -0.3%$335,200 +0.6%
        2021$3,780 +0.6%$333,333 +0.6%
        2020$3,759 +0.6%$331,467 +0.6%
        2019$3,738 +3.8%$329,600 +3.8%
        2018$3,602 +3.9%$317,667 +3.9%
        2017$3,467 -10.9%$305,733 +4.1%
        2016$3,892 $293,800
        2015$3,892 $293,800
        2014$3,892 $293,800 -13.7%
        2013-- $340,600
        2012-- $340,600
        2011-- $340,600 -19.2%
        2010-- $421,420 +7.5%
        2009-- $391,932 +8.1%
        2008-- $362,446 +8.9%
        2007-- $332,960 +320%
        2006-- $79,282 +30%
        2005-- $60,986 +42.9%
        2004-- $42,690 +6.4%
        2003-- $40,122 +6.8%
        2002-- $37,556 +7.3%
        2001-- $34,990
        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: 21620

        Getting around

        1 / 100
        Car-Dependent
        41 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Kent 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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