Chestertown Homes with Golf Course Amenities

Chestertown Homes with Golf Course Amenities

Welcome to Chestertown, Maryland—a charming gem nestled in the heart of Kent County. This picturesque town, steeped in rich history and vibrant culture, offers a unique blend of small-town charm and modern amenities. With its stunning waterfront views along the Chester River and beautifully preserved colonial architecture, Chestertown is a delightful place to call home.

For golf enthusiasts, Chestertown presents an exceptional opportunity to live in proximity to stunning homes with golf course amenities. Imagine waking up to lush green fairways right outside your window, where you can indulge in your passion for golf without ever straying far from home. The nearby golf courses offer not just an excellent playing experience but also a sense of community, with social events and networking opportunities that bring residents together.

In addition to golfing, Chestertown boasts a thriving arts scene, quaint boutiques, and a variety of dining options that cater to all tastes. The annual Chestertown Tea Party Festival and the local farmers' market are just a few of the community events that showcase the town's rich heritage and vibrant spirit.

Whether you're looking for a cozy cottage or a spacious family home, Chestertown's real estate market has something for everyone. The combination of scenic beauty, recreational opportunities, and a close-knit community makes this town an ideal place for those seeking a serene lifestyle with plenty of activities at their fingertips. Come discover the perfect blend of relaxation and recreation in Chestertown, where your dream home awaits amidst the rolling hills and golf course greens.

Newest Chestertown Homes with Golf Course Amenities

$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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