Great Oak Estates Homes with Inside Access Garage Description

Great Oak Estates Homes with Inside Access Garage Description

Welcome to Great Oak Estates, a picturesque subdivision nestled in the heart of Chestertown, Maryland. This charming community is perfectly situated in Kent County, where the serene beauty of nature meets the vibrancy of small-town living. Great Oak Estates offers a delightful blend of modern conveniences and a tranquil lifestyle, making it an ideal place for families, retirees, and everyone in between.

The homes in Great Oak Estates are designed with both comfort and functionality in mind. Each property features an inside access garage, providing you with the convenience of direct entry into your home, even on the rainiest of days. Imagine the ease of unloading groceries or bringing in the kids after a day of adventure without the hassle of stepping outside. These thoughtful designs ensure that every aspect of daily life is as seamless as possible.

As you explore this enchanting community, you’ll find tree-lined streets, well-maintained parks, and a welcoming atmosphere that encourages neighborly connections. Great Oak Estates is not just a place to live; it’s a place to thrive. With easy access to local amenities, shopping, and dining, you’ll have everything you need right at your fingertips.

Whether you’re looking for a cozy family home or a peaceful retreat, Great Oak Estates offers a variety of options tailored to suit your lifestyle. Come discover the charm and warmth of this remarkable subdivision, and envision your future in a place where community and comfort come together beautifully.

Newest Great Oak Estates Homes with Inside Access Garage Description

$649,000
4 Beds ⋅ 3 Baths
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.

22400 Great Oak Landing Rd., Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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