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MLS: #MDKE2006946, Listed By: Terri Kulp, Coldwell Banker Chesapeake Real Estate Company, Source:Bright MLS

22400 Great Oak Landing Rd. Rd

CHESTERTOWN, MD 21620
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Bed 4

Bed

Bath 3

Bath

SqFt2,864

Sqft

Acres1.03

Acres(Lot)

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-n ew carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

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Detail Ic Property Details

Property Type : Residential

Price : $649,000

AD Id : 89930493

MLS Id : MDKE2006946

Beds : 4

Lot Size : 1.03 Acres

Living Area Size : 2,864

Year Built : 2000

Garage : 2

County : KENT

Subdivision: Great Oak Estates

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total beds: 4

    Bathroom Information

    Total Baths: 3 Full Baths: 3

    Room Information

    Basement: Crawl Space
  • Flooring Information

    Carpet, Wood, Hardwood, Ceramic Tile
  • Roofing Information

    Shingle
  • Interior Features

    Eat-in Kitchen, Ceiling Fan(s), Pantry, Recessed Lighting, Walk-In Closet(s), Built-in Features Roof: Shingle Appliances: Gas Range, Gas Oven, Cooktop, Water Purifier, Electric Water Heater, Dishwasher, Disposal, Exhaust Fan, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Microwave Laundry Features: Laundry Room, Main Level Window Features: Window Coverings, Bay Window(s), ENERGY STAR Qualified Windows, Window Treatments
  • Heating & Cooling

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

  • Building Information

    Year Built: 2000 Building Area Total: 3464 Construction Materials: Vinyl Siding Patio And Porch Features: Patio Pool Features: None Private Pool: No View: Pasture, Trees/Woods, Garden Association Fee Frequency: Annually

  • Lot Information

    Lot Size Acres: 1.03 Lot Size Source: Assessor Lot Size Square Feet: 44867 Lot Description: Front Yard, Few Trees

    Property Information

    Subdivision: GREAT OAK ESTATES Source Property Type: Residential Postal Code Plus 4: 4107 Property SubType: Single Family Residence Levels: Two Property Age: 26

  • Listing Price Information

    Listing Price: $649000

  • Tax Information

    Parcel Number: 1506025099 Tax Lot: 65 Tax Year: 2026 Annual Tax: $4695

  • Parking Information

    Parking Total: 8 Garage Door Opener, Gravel, Garage, Driveway, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 2 Pets Allowed: Yes
    Homeowners Association Information
    Has Association: Yes HOA: $100.00 Association Amenities: Golf Course, Marina

  • School Information

    Elementary School:
    Junior High School:
    Senior High School: KENT COUNTY
  • Utility Information

    Cable Available, Propane
  • Location Information

    Direction: From Chestertown, take Rt. 20 going towards Rock Hall. Right onto Flatland Rd. Turn left onto Melitota Rd.. Go through stop sign onto Handy Point Road (straight). Take a left onto Great Oak Landing - Safe Harbor Marina sign on your left. Once past the farm, the house will be on your right. WaterSource: Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
204 Double Creek Road, Chestertown, MD, 21620 $545,000 3 3 2,927 2,927 SqFt
240 Merganser Drive, Chestertown, MD, 21620 $365,000 3 2 1,120 1,120 SqFt
124 Wilton Road, Chestertown, MD, 21620 $299,900 3 1 1,056 1,056 SqFt
222 Dutchess Road, Chestertown, MD, 21620 $320,000 3 2 1,096 1,096 SqFt
123 Heath Road, Chestertown, MD, 21620 $349,000 3 2 1,792 1,792 SqFt
240 Round Top Road, Chestertown, MD, 21620 $295,000 3 2 1,132 1,132 SqFt
216 Birch Run Road, Chestertown, MD, 21620 $750,000 3 3 2,176 2,176 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
210 N Queen Street, Chestertown, MD, 21620 $735,000 4 3 2,730 2,730 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 08/28/2026 @ 16:07

MLS: MDKE2006946 LISTED BY: Terri Kulp, Coldwell Banker Chesapeake Real Estate Company 410-778-0330 SOURCE: Bright MLS

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