Great Oak Estates Homes with Built In Garage Description

Great Oak Estates Homes with Built In Garage Description

Welcome to Great Oak Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal place to call home. Surrounded by lush landscapes and mature oak trees, Great Oak Estates provides a serene environment where nature and community coexist harmoniously.

The homes in Great Oak Estates are designed with modern living in mind, featuring spacious layouts that cater to both comfort and functionality. Each residence comes equipped with a built-in garage, providing ample space for your vehicles and additional storage. This thoughtful feature not only enhances the aesthetic appeal of the homes but also adds a layer of convenience for busy families and individuals alike.

Residents of Great Oak Estates enjoy the best of both worlds—easy access to the vibrant downtown Chestertown, with its delightful shops, restaurants, and cultural attractions, while also having the opportunity to retreat to the peaceful embrace of their community. The nearby Chester River offers recreational activities like boating, fishing, and scenic walks along the waterfront, ensuring that outdoor enthusiasts will never run out of adventures.

Whether you're a first-time homebuyer or looking to downsize, Great Oak Estates presents a unique opportunity to invest in a lifestyle that prioritizes comfort, community, and the beauty of nature. Come explore the inviting charm of Great Oak Estates and discover your dream home in this idyllic Maryland community!

Newest Great Oak Estates Homes with Built In 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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