Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$824,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,353 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 8/1 11:00 AM - 1:00 PM

8999 Orchard Drive,Chestertown, MD 21620

8999 Orchard DriveChestertownMD21620

Get directions
See This Home
Save This Home
See This Home
Save 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 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

Full Property Details for 8999 Orchard Dr

General

  • Price: $824,900
  • Taxes: $6,813 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006786
  • Updated: 7/25/2026
  • Added to Site: 5 day(s) ago

Interior

  • Rooms/Areas: 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
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Fireplace - Glass Doors, Gas/Propane, Mantel(s)
  • Appliances: 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
  • Flooring: Carpet, Ceramic Tile, Hardwood, Heated, Laminate Plank

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 4
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Dryer In Unit, Has Laundry, Main Floor, Washer In Unit, Lower Floor

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground

Exterior

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

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking Features: Asphalt Driveway
  • Parking Type: Off Street, Attached Garage, Driveway
  • Garage Description: Garage - Side Entry, Garage Door Opener, Inside Access

Location

  • County: KENT
  • Subdivision: ORCHARD HILL
  • Driving Directions: From Chestertown head towards Rock Hall on Rt. 20, turn right on Orchard Drice, then an immediate left, house is on left.
  • Location Details: Rural

School Information

  • School District: Kent County Public Schools

Community

  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C, Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Heat Pump(s), Zoned
  • Heating Fuel: Electric, Propane - Owned
  • Water Heater: Tankless

Utilities

  • Sewer: Private Septic Tank
  • Water: Well
  • Utility Description: Cable TV Available, Electric Available, Phone Available, Propane

Structural Information

  • Architectural Style: Craftsman
  • Structure Type: Detached
  • Builder: DREAM HOME BUILDERS
  • Construction: Vinyl Siding
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Connecting Stairway, Daylight, Full, Heated, Improved, Outside Entrance, Partially Finished, Sump Pump, Walkout Level, Windows
  • Foundation: Brick/Mortar, Concrete Perimeter
  • Roof: Architectural Shingle
  • Walls/Ceilings: Cathedral Ceilings, Dry Wall
  • Windows: Double Pane, Screens
  • Doors: Sliding Glass
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 4,353
  • Sq. Ft. Source: Assessor
  • Living Area: 4,353 Sq. Ft.
  • Finished Above Grnd: 2,653 Sq. Ft.
  • Finished Below Grnd: 1,700 Sq. Ft.
  • Year Built: 2006
  • Year Built Source: Assessor
  • Property Condition: Very Good

Unit Information

Unit 1

  • Bathrooms-Lower: 1

Additional Structures

  • Other Structures: Gazebo, Shed

Lot Features

  • Lot Size (Acres): 2.23
  • Lot Size (Sq. Ft.): 97,139
  • Lot Size Source: Assessor
  • Street/Road Desc.: Black Top
  • Zoning: RR
  • Lot Description: Landscaping, Front Yard, Poolside, Private, Rear Yard, Level, SideYard(s)
  • Fencing (Description): Board, Partially, Rear, Wood

Financial Considerations

  • Price Per Sq. Ft.: $310.93
  • Assessment Year: 2026
  • County Tax: $6,813
  • County Tax Freq: Annually
  • Tax w/Assessment: $623,867
  • Tax Amount: $6,813
  • Tax Year: 2026
  • Tax Total Finished Sq. Ft.: 4353

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 2

Listed by Coldwell Banker Chesapeake Real Estate Company, Terri L Kulp

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 8999 Orchard Dr —

  • Terri L Kulp

    Coldwell Banker Chesapeake Real Estate Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 8999 Orchard Dr

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-51.5 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-81.9 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 8999 Orchard Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/25/2026
Listed
$824,900
31.98%
MLS
6/13/2022
Sold
$625,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 8999 Orchard Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,525
5%
$600,800
17%
2024
$4,291
12%
$512,267
21%
2023
$3,828
—
$423,733
26%
2022
$3,828
—
$335,200
1%
2020
$3,819
—
$333,333
1%
2021
$3,819
1%
$331,467
1%
2020
$3,798
4%
$329,600
4%
2019
$3,662
4%
$317,667
4%
2018
$3,527
4%
$305,733
4%
2017
$3,392
—
$293,800
—
2015
$3,392
-14%
$293,800
-14%
2014
$3,922
—
$340,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 8999 Orchard Dr

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Coldwell Banker Chesapeake Real Estate Company, Terri L Kulp

Similar Properties near 8999 Orchard Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

4020 Eastern Neck Rd, Rock Hall, MD 21661 - Photo 1
$799,000

4020 Eastern Neck Rd  Rock Hall, MD 21661

  • Single Family
  • Active
  • 4
    Beds
  • 2
    Total Baths
  • 3,300
    Sq. Ft.
Listed by Rock Hall Properties Real Estate, Cindy Genther
106 Queen Street S, Chestertown, MD 21620 - Photo 1
$829,000

106 Queen Street S  Chestertown, MD 21620

  • Single Family
  • Active
  • 3
    Beds
  • 4
    Total Baths
  • 2,472
    Sq. Ft.
Listed by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair

Just Listed near 8999 Orchard Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

12733 Still Pond Rd, Still Pond, MD 21667 - Photo 1 Just Listed
$299,900

12733 Still Pond Rd  Still Pond, MD 21667

  • Single Family
  • Active
  • Updated 17 hours ago
  • 6
    Beds
  • 2
    Total Baths
  • 3,270
    Sq. Ft.
Listed by Sell Your Home Services, Daniel J. Demers
21352 Allens Ln, Rock Hall, MD 21661 - Photo 1 Just Listed
$330,000

21352 Allens Ln  Rock Hall, MD 21661

  • Single Family
  • Active
  • Updated 9 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,710
    Sq. Ft.
Listed by Rock Hall Properties Real Estate, Robin Fithian
21128 Striper Run, Rock Hall, MD 21661 - Photo 1 Just Listed
$325,000

21128 Striper Run  Rock Hall, MD 21661

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,520
    Sq. Ft.
Listed by EXP Realty, LLC, ETHAN ANDREW HARVEY
21610 Hidden Creek Dr, Rock Hall, MD 21661 - Photo 1 Just Listed
$699,000

21610 Hidden Creek Dr  Rock Hall, MD 21661

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,185
    Sq. Ft.
Listed by Whitetail Properties Real Estate, LLC, Michael M Arajakis II

Price Reduced near 8999 Orchard Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

26765 Dutchtown Rd, Still Pond, MD 21667 - Photo 1 Price Reduced
-$5,900 (-4.22%)
$134,000

26765 Dutchtown Rd  Still Pond, MD 21667

  • Lots/Land
  • Active
  • Updated 2 days ago
  • 0.5
    Acres
Listed by DMV Prime Properties, Michael A. Kelczewski
201 Ericsson Ave, Betterton, MD 21610 - Photo 1 Price Reduced
-$34,000 (-7.56%)
$415,900

201 Ericsson Ave  Betterton, MD 21610

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,280
    Sq. Ft.
Listed by Coldwell Banker Waterman Realty, Jonathan J Olsavsky and Coldwell Banker Waterman Realty, Steven S Saunders
6374 Rock Hall Rd, Rock Hall, MD 21661 - Photo 1 Price Reduced
-$7,000 (-2.54%)
$269,000

6374 Rock Hall Rd  Rock Hall, MD 21661

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,000
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland
21899 Lovers Ln, Rock Hall, MD 21661 - Photo 1 Price Reduced
-$15,000 (-10.35%)
$129,900

21899 Lovers Ln  Rock Hall, MD 21661

  • Mobile Home
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 800
    Sq. Ft.
Listed by Sell Your Home Services, Daniel J. Demers

Recent Sales near 8999 Orchard Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

6 Byford Ct, Chestertown, MD 21620 - Photo 1 Sold
$749,500

6 Byford Ct  Chestertown, MD 21620

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 3,136
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, Peter D Heller
Sold by Cross Street Realtors LLC, Richard Keaveney
25475 Turnberry Ct, Chestertown, MD 21620 - Photo 1 Sold
$825,000

25475 Turnberry Ct  Chestertown, MD 21620

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 5,290
    Sq. Ft.
Listed by Taylor Properties, Lona Sue Todd
Sold by Unrepresented, Unrepresented
205 River Rd, Chestertown, MD 21620 - Photo 1 Sold
$855,000

205 River Rd  Chestertown, MD 21620

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,877
    Sq. Ft.
Listed by Clark & Co Realty, LLC, Karen T Clark
Sold by Cross Street Realtors LLC, Richard Keaveney
25999 Lambs Meadow Rd, Worton, MD 21678 - Photo 1 Sold
$765,000

25999 Lambs Meadow Rd  Worton, MD 21678

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 3,046
    Sq. Ft.
Listed by TTR Sotheby's International Realty, Liddy Campbell
Sold by Monument Sotheby's International Realty, Alana E Dixon

8999 Orchard Drive, Chestertown, MD 21620 (MLS# MDKE2006786) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 8999 Orchard Drive is currently listed for $824,900 and was received on July 25, 2026. Want to learn more about 8999 Orchard Drive? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

Tour this property