22400 Great Oak Landing Rd.

Chestertown, MD 21620
  • $649,000

    Price
  • 4

    Bed
  • 3

    Bath
  • 2,864

    SqFt

About the Listing CBCE2 - 3088687

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 Highlights

Status Active
Days on Site 2
Property Type Residential
MLS ® MDKE2006946
Year Built 2000
Total Square Footage 2,864
Lot/Acreage 1.03
County Kent
Neighborhood Great Oak Estates
HOA Dues 100/Annually
School District Kent County Public Schools
High School Kent County

Interior Details

  • Bedrooms: 4
  • Bathrooms: 3 Full
  • 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, Water Heater
  • Air Cond: Central A/C
  • Heating: Forced Air
  • Fireplaces: 1, Screen,Gas/Propane,1 Fireplace
  • Floor: Hardwood,Carpet,Ceramic Tile
  • Above Ground Sq Ft: 2864
  • Below Ground Sq Ft: 0
  • Basement:
  • Other: 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,No Pet Restrictions,Pets Allowed,Main Floor Bedrooms: 2
  • Water: Well

Exterior Details

  • Lot Description: Backs to Trees,Front Yard,Landscaping,Partly Wooded,Not New Construction,Horse Property: No
  • Garage Capacity: 2 car
  • Parking Spaces: 8
  • Zoning: RR
  • Roof: Architectural Shingle
  • Others: Private Beach,Pool - Outdoor,Golf Course,Marina/Marina Club
  • Sewer: Private Septic Tank
  • Parking Features: Gravel Driveway,Garage Door Opener,Garage - Side Entry,Built In,Inside Access,Driveway,Attached Garage,4+ Spaces,3+ Spaces,2+ Spaces,1+ Spaces

Financial Details

  • Tax Amount: $4,695
  • Taxes w/Assessments: N/A
  • Tax/Property ID: N/A
  • Tax Year: 2026

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22400 Great Oak Landing Rd. Chestertown, MD 21620

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Originating MLS: BRIGHT_MAIN

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Sarah Forti

Realtor and Team Owner of Forti Homes | Forti Homes | KW Devon Wayne

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