231 RICHARD Dr

Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town convenience.
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With five (plus) bedrooms accommodating up to fourteen guests and three full baths, the home is designed for comfort, flexibility, and enjoyment. Multiple indoor and outdoor gathering spaces make it ideal for those seeking a full-time residence, a weekend retreat, a multi-generational destination, or a strong investment property with outstanding rental potential.
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On the main level, a cozy den with a wood-burning fireplace captures Chester River views, creating a warm and welcoming spot to relax after a day on the water. Additional living spaces provide room for groups to spread out—whether entertaining, working remotely, or simply taking a quiet moment to unwind. The primary suite offers its own private vantage point with a picture window overlooking the pool and riverfront—perfect for greeting the sunrise or watching wildlife glide across the water.
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Outdoor living is where this property truly shines. Enjoy a covered patio for shaded summer crab feasts, a large deck with a stone fireplace for crisp evenings, and an in-ground pool that looks out toward the shore. With immediate water access, you’ll launch kayaks, paddle boards, and jet skis right from your backyard—ideal for embracing the river lifestyle. A two-car attached garage provides convenient storage for gear, bikes, and all the water toys. It could also be the perfect space to keep your street legal golf cart which the Town Of Chestertown now allows!
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Your new home is also just a short walk from the full-service Chestertown Marina with the potential for a transferable slip—already paid through the 2026 boating season—ensuring you can enjoy hassle-free access to Chester River fun. Additionally, it's a quick ride to the Chester River Yacht & Country Club, where you can indulge in 18 holes of golf, relax by the pool, enjoy happy hour or meals at the full restaurant and bar, and partake in a host of other fantastic member benefits.
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Whether you’re making it your full-time home, your getaway from the city, or your next strategic investment, this property delivers the best of Chestertown living—waterfront, walkable, and wonderfully welcoming. Embrace a lifestyle of leisure and convenience in this exceptional location.