Chestertown Homes with Cape Cod Style

Chestertown Homes with Cape Cod Style

Welcome to Chestertown, Maryland, a charming riverside town nestled in the heart of Kent County. Known for its rich history and vibrant arts scene, Chestertown offers a unique blend of small-town charm and modern amenities. With its picturesque streets lined with historic homes, boutique shops, and inviting cafes, this town is a hidden gem on the Eastern Shore. The scenic Chester River flows through the heart of the community, providing opportunities for boating, fishing, and leisurely strolls along the waterfront.

One of the standout architectural styles you’ll find in Chestertown is the beloved Cape Cod home. These classic dwellings, characterized by their steeply pitched roofs, symmetrical facades, and dormer windows, exude a timeless appeal that resonates with both history buffs and modern homeowners alike. Cape Cod homes in Chestertown often feature inviting front porches, spacious interiors, and cozy fireplaces, making them perfect for both entertaining and relaxing with family.

Living in a Cape Cod-style home in Chestertown means embracing a lifestyle that celebrates both comfort and community. With local farmers' markets, seasonal festivals, and a welcoming atmosphere, you’ll find that this town is not just a place to live, but a place to thrive. Whether you're drawn to the area's rich maritime heritage, the vibrant arts scene, or the stunning natural beauty surrounding you, Chestertown is the perfect backdrop for your next chapter. Explore our listings of Cape Cod homes today and discover the charm and warmth that this delightful town has to offer!

Newest Chestertown Homes with Cape Cod Style

$424,900
5 Beds 3 Baths
Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAid dishwasher. The French-door refrigeratorincludes a front water and ice dispenser for added convenience. Attractive ceiling fans throughout the home add both comfort and style. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. With five bedrooms, the layout offers excellent flexibility, and the fifth bedroom can also serve as a home office, guest room, or additional flex space. The partially finished one-car garage offers added versatility beyond traditional vehicle parking and storage. It can also serve as a game room, entertainment area, recreation space, hobby room, home gym, or additional flex space, giving buyers even more options for how they use the home. Step outside to an expanded rear deck, hot tub, and fire-pit/seating area, ideal for relaxing or entertaining. Boating enthusiasts will appreciate the nearby seasonal marina with restaurants and a dive bar 3 blocks away and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. Additional updates include an approximately two-year-old water heater and a private well with an upgraded water-treatment/softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Whether used as a primary residence, vacation home, weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package.

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

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