Change Real Estate Presents:

22400 Great Oak Landing Rd.
Chestertown MD 21620

For Sale: $649,000.00 Active

List Date: 2026-08-23

Open House: Sep 19, 2026 at 11:00 AM to 01:00 PM
Chestertown
4 bedrooms
3 bathrooms
2,864 build ft2
1.03 land acres

About This Property

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-new 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.

Listing Agent: Terri L Kulp. Coldwell Banker Chesapeake Real Estate Company 301-462-9976 terrikulp@cbchesapeake.com

Property Features

Location Information
County:
Subdivision: GREAT OAK ESTATES
click to open map in a new window
Interior Features
Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer - Electric, Dryer - Front Loading, Exhaust Fan, Extra Refrigerator/Freezer, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Stove, Washer, Water Conditioner - Owned, WaterHeater
Interior: Breakfast Area, Floor Plan - Traditional, Attic, Built-Ins, Carpet, Ceiling Fan(s), Entry Level Bedroom, Formal/Separate Dining Room, Kitchen - Eat-In, Pantry, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Water Treat System, Window Treatments, Wood Floors
Laundry:
Furnished: None
Flooring: Hardwood, Carpet, CeramicTile
Water: Well
Cooling: Central A/C
Heating: Forced Air
Fireplaces: 1
Windows: Bay/Bow, ENERGY STAR Qualified
Utilities: Cable TV, Propane
Sewer: Private Septic Tank
Rooms
Room Type: Bedroom 3
Dimensions: 17 X 15
Features: Flooring - Carpet, Walk-In Closet(s), Ceiling Fan(s)
Level: Upper 1
Room Type: Bedroom 4
Dimensions: 15 X 14
Features: Flooring - Carpet, Walk-In Closet(s), Ceiling Fan(s)
Level: Upper 1
Room Type: Bathroom 3
Level: Upper 1
Room Type: Attic
Features: Attic - Floored
Level: Upper 1
Room Type: Foyer
Features: Flooring - HardWood
Level: Main
Room Type: Living Room
Features: Flooring - Solid Hardwood, Lighting - Recessed, Window Treatments
Level: Main
Room Type: Dining Room
Dimensions: 15 X 13
Features: Flooring - HardWood, Lighting - Recessed, Window Treatments
Level: Main
Room Type: Family Room
Dimensions: 16 X 14
Features: Flooring - HardWood, Fireplace - Gas, Built-Ins
Level: Main
Room Type: Kitchen
Dimensions: 14 X 12
Features: Flooring - HardWood, Lighting - Recessed, Countertop(s) - Solid Surface, Double Sink, Kitchen - Gas Cooking
Level: Main
Room Type: Breakfast Room
Dimensions: 14 X 9
Features: Flooring - HardWood, Built-Ins, Lighting - Recessed
Level: Main
Room Type: Primary Bedroom
Dimensions: 17 X 15
Features: Flooring - Carpet, Walk-In Closet(s), Ceiling Fan(s), Window Treatments
Level: Main
Room Type: Primary Bathroom
Level: Main
Room Type: Bedroom 2
Dimensions: 14 X 12
Features: Flooring - Carpet, Ceiling Fan(s)
Level: Main
Room Type: Laundry
Dimensions: 12 X 8
Features: Flooring - Ceramic Tile, Pantry
Level: Main
Exterior Features
Year Built: 2000
Legal Subdivision: Great Oak Estates
Subdivision Name: Great Oak Estates
Exterior Features: Private Beach
Parking: Gravel Driveway
Garage Spaces: 2.0
Association Fee: $100.00 (Annually)
Association Amenities: Pool - Outdoor, GolfCourse, Marina/Marina Club
Schools
Elementary School: None
Junior High School: None
High School: Kent County

IDXListing Courtesy of Terri L Kulp. Coldwell Banker Chesapeake Real Estate Company 301-462-9976 terrikulp@cbchesapeake.com

Property Photos [Click to enlarge]

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