8999 Orchard Dr, Chestertown, MD 21620
Local realty services provided by:CENTURY 21 The Real Estate Store
8999 Orchard Dr,Chestertown, MD 21620
$824,900
- 5 Beds
- 4 Baths
- 4,353 sq. ft.
- Single family
- Pending
Listed by: terri l kulp
Office: coldwell banker chesapeake real estate company
MLS#:MDKE2006786
Source:BRIGHTMLS
Price summary
- Price:$824,900
- Price per sq. ft.:$189.5
About this home
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 in-ground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. The owners have ordered a new, heavy duty liner, perfect for pets and kids, to be installed with the closing of the pool around the end of September. 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...
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Home facts
- Year built:2006
- Subdivision & Development:ORCHARD HILL
- Listing ID #:MDKE2006786
- Added:96 day(s) ago
- Updated:October 27, 2026 at 08:37 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Flooring:Carpet, Ceramic Tile, Hardwood, Heated, Laminate Plank
- Dining Description:Dining Area, Dining Room, Formal/Separate Dining Room
- Bathrooms Description:Bathroom 1, Half Bath, Primary Bath(s), Primary Bathroom
- Kitchen Description:2nd Kitchen, Built-Ins, Cooktop, Dishwasher, Exhaust Fan, Extra Refrigerator/Freezer, Kitchen - Gourmet, Kitchen - Island, Kitchen - Table Space, Microwave, Oven - Double, Oven/Range - Electric, Oven/Range - Gas, Range Hood, Refrigerator, Stainless Steel Appliances, Stove, Water Heater - Tankless, Wine Storage
- Bedroom Description:Primary Bedroom, Walk In Closet(s)
- Basement:Yes
- Basement Description:Connecting Stairway, Daylight, Full, Heated, Improved, Outside Entrance, Partially Finished, Sump Pump, Walkout Level, Windows
- Living area:4,353 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C, Heat Pump(s)
- Heating:Electric, Forced Air, Heat Pump(s), Propane - Owned, Zoned
Structure and exterior
- Roof:Architectural Shingle
- Year built:2006
- Building area:4,353 sq. ft.
- Lot area:2.23 Acres
- Lot Features:Front Yard, Landscaping, Level, Poolside, Private, Rear Yard, Rural, SideYard(s)
- Architectural Style:Craftsman
- Construction Materials:Vinyl Siding
- Exterior Features:Exterior Lighting, Outbuilding(s), Patio(s), Porch(es)
- Foundation Description:Brick/Mortar, Concrete Perimeter
- Levels:3 Story
Utilities
- Water:Well
- Sewer:Private Septic Tank
Finances and disclosures
- Price:$824,900
- Price per sq. ft.:$189.5
- Tax amount:$6,813 (2026)
Features and amenities
- Laundry features:Dryer, Dryer - Electric, Dryer - Front Loading, Dryer In Unit, Has Laundry, Laundry, Washer, Washer - Front Loading, Washer In Unit, Washer/Dryer Stacked
- Amenities:Built-Ins, Cable TV Available, Ceiling Fan(s), Double Pane Windows, Electric Available, Phone Available, Water Treat System, Window Treatments
- Pool features:Heated, In Ground
Parking
- Parking description:Asphalt Driveway, Attached Garage, Garage - Side Entry, Garage Door Opener, Inside Access, Off Street
- Garage:Yes
- Garage spaces:2
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