$824,900

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… Read More 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 Read Less

Courtesy of Terri L Kulp, Coldwell Banker Chesapeake Real Estate Company 410-778-0330

Listing Snapshot

Days Online

Last Updated

Oct 5, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

4,353

Lot Size

2.23 Acres

Year Built

2006

MLS Number

MDKE2006786

Additional Details

Property Access

Road Surface: Black Top

Appliances & Equipment

Dryer - Front Loading, Oven - Double, Refrigerator, Dryer - Electric, Extra Refrigerator/Freezer, Range Hood, Stainless Steel Appliances, Washer - Front Loading, Cooktop, Dishwasher, Dryer, Exhaust Fan, Microwave, Oven/Range - Gas, Oven/Range - Electric, Stove, Washer, Washer/Dryer Stacked, Water Heater - Tankless, Water Conditioner - Owned

Basement

Connecting Stairway, Daylight, Full, Heated, Improved, Outside Entrance, Partially Finished, Sump Pump, Walkout Level, Windows

Building

Built in 2006, Living area: 4353, Levels: 3, Construction Materials: Vinyl Siding

Cooling

Ceiling Fan(s), Central A/C, Heat Pump(s)

Doors

Sliding Glass

Accessibility Features

Other Bath Mod, Roll-in Shower

Exterior Features

Patio/Porch Features: Porch(es), Patio(s), Exterior Lighting, Outbuilding(s)

Fence

Board, Partially, Rear, Wood

Fireplaces

1 fireplace, Fireplace - Glass Doors, Gas/Propane, Mantel(s)

Floors

Carpet, Ceramic Tile, Hardwood, Heated, Laminate Plank

Foundation

Brick/Mortar, Concrete Perimeter

Garage

2 spaces

Heating

Forced Air, Heat Pump(s), Zoned

Interior Features

Kitchen - Island, Kitchen - Table Space, Dining Area, Primary Bath(s), Window Treatments, Wood Floors, Ceiling Fan(s), Kitchen - Gourmet, Walk-in Closet(s), Water Treat System, Wine Storage, 2nd Kitchen, Bathroom - Walk-In Shower, Built-Ins, Floor Plan - Open, Formal/Separate Dining Room

Lot

2.23 acres, Landscaping, Front Yard, Poolside, Private, Rear Yard, Level, SideYard(s)

Parking

Asphalt Driveway

Pets Policy

Allowed: No Pet Restrictions

Pool

Heated, In Ground

Property

Very Good, Other structures: Above Grade, Below Grade

Roof

Architectural Shingle

Sewer

Private Septic Tank

Taxes

Additional parcels description:, Annual Amount: $6,813, Lot: 2, Year: 2026, Zoning: RR

Utilities

Cable TV Available, Electric Available, Phone Available, Propane, Water Source: Well

Windows

Double Pane, Screens

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8999 ORCHARD DRIVE

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