Great Oak Estates Homes with Backs to Trees Lot features

Great Oak Estates Homes with Backs to Trees Lot features

Welcome to Great Oak Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers an idyllic blend of suburban tranquility and natural beauty, making it the perfect place to call home. With its serene surroundings, Great Oak Estates is designed for those who appreciate the harmony of nature and modern living.

Each home in Great Oak Estates boasts unique architectural designs and spacious layouts, catering to a variety of lifestyles. One of the standout features of this community is the enchanting homes that back to lush, mature trees. Imagine waking up each morning to the soothing sounds of rustling leaves and chirping birds, while enjoying the privacy and serenity that comes with having nature as your backyard. These tree-lined lots not only provide a picturesque backdrop but also create a natural habitat for wildlife, enriching your everyday life with the beauty of the outdoors.

Located in Kent County, Great Oak Estates is just a short drive from the vibrant historic downtown Chestertown, where you can enjoy charming shops, delightful eateries, and cultural events. The community is also conveniently situated near parks, hiking trails, and the scenic Chester River, offering endless opportunities for outdoor recreation.

Whether you're a growing family, a retiree seeking peace, or anyone in between, Great Oak Estates is a place where you can create lasting memories in a serene setting. Come explore the beauty of this community and discover the perfect home that awaits you!

Newest Great Oak Estates Homes with Backs to Trees Lot features

$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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