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MLS: #MDKE2006786, Listed By: Terri Kulp, Coldwell Banker Chesapeake Real Estate Company, Source:Bright MLS

8999 Orchard Drive

CHESTERTOWN, MD 21620
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Bed 5

Bed

Bath 4

Bath

SqFt4,353

Sqft

Acres2.23

Acres(Lot)

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

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Detail Ic Property Details

Property Type : Residential

Price : $824,900

AD Id : 88320427

MLS Id : MDKE2006786

Beds : 5

Lot Size : 2.23 Acres

Living Area Size : 4,353

Year Built : 2006

Garage : 2

County : KENT

Subdivision: Orchard Hill

  • Map Map

Map

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Map Nearby Areas

Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 4 Full Baths: 3 Half Baths: 1

    Room Information

    Has Basement: Yes Basement: Exterior Entry, Walk-Out Access, Daylight, Full, Partially Finished, Sump Pump
  • Flooring Information

    Laminate, Wood, Carpet, Ceramic Tile, Hardwood
  • Roofing Information

    Shingle
  • Interior Features

    Kitchen Island, Ceiling Fan(s), Walk-In Closet(s), Cathedral Ceiling(s), Built-in Features, Open Floorplan Roof: Shingle Appliances: Double Oven, Electric Range, Electric Oven, Gas Range, Gas Oven, Cooktop, Washer, Water Purifier, Refrigerator, Range Hood, Stainless Steel Appliance(s), Dishwasher, Dryer, Exhaust Fan, Microwave, Washer/Dryer Stacked, Tankless Water Heater Laundry Features: Laundry Room, Main Level, Lower Level Window Features: Window Coverings, Double Pane Windows, Screens, Window Treatments
  • Heating & Cooling

    Has Heating: Yes Heating: Exhaust Fan, Electric, Propane, Forced Air, Zoned, Heat Pump Has Cooling: Yes Cooling: Central Air, Heat Pump, Ceiling Fan(s), Electric

  • Building Information

    Year Built: 2006 Building Area Total: 4353 Construction Materials: Vinyl Siding Patio And Porch Features: Porch, Patio Pool Features: Heated, In Ground, Private Private Pool: Yes
  • Exterior Features

    Exterior Features: Lighting

  • Lot Information

    Lot Size Acres: 2.23 Lot Size Source: Assessor Lot Size Square Feet: 97139 Lot Description: Front Yard, Private, Level, Back Yard

    Property Information

    Subdivision: ORCHARD HILL Source Property Type: Residential Postal Code Plus 4: 3407 Property SubType: Single Family Residence Levels: Three Or More Property Age: 20

  • Listing Price Information

    Listing Price: $824900

  • Tax Information

    Parcel Number: 1504023382 Tax Lot: 2 Tax Year: 2026 Annual Tax: $6813

  • Parking Information

    Parking Total: 6 Garage Door Opener, Asphalt, Off Street, Garage, Driveway, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 2 Pets Allowed: Yes

  • Utility Information

    Cable Available, Phone Available, Propane, Electricity Available
  • Location Information

    Direction: From Chestertown head towards Rock Hall on Rt. 20, turn right on Orchard Drice, then an immediate left, house is on left. WaterSource: Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Preston Lane, Chestertown, MD, 21620 $525,000 3 3 2,824 2,824 SqFt
1904 Pondtown Road, Chestertown, MD, 21620 $265,000 3 1 1,967 1,967 SqFt
204 Double Creek Road, Chestertown, MD, 21620 $565,000 3 3 2,927 2,927 SqFt
240 Merganser Drive, Chestertown, MD, 21620 $365,000 3 2 1,120 1,120 SqFt
222 Dutchess Road, Chestertown, MD, 21620 $320,000 3 2 1,096 1,096 SqFt
517 Round Top Road, Chestertown, MD, 21620 $299,900 3 1 1,248 1,248 SqFt
202 Royston Shores Road, Chestertown, MD, 21620 $1,200,000 4 3 2,292 2,292 SqFt
101 Coleman Drive, Chestertown, MD, 21620 $519,900 3 3 2,268 2,268 SqFt
201 River Road, Chestertown, MD, 21620 $629,900 3 2 2,430 2,430 SqFt
103 Maple Avenue, Chestertown, MD, 21620 $615,000 4 3 4,536 4,536 SqFt

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 07/27/2026 @ 20:08

MLS: MDKE2006786 LISTED BY: Terri Kulp, Coldwell Banker Chesapeake Real Estate Company 410-778-0330 SOURCE: Bright MLS

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