Eastern Shore of Maryland Real Estate Blog - Eastern Shore Real Estate

201 Birch Run Road, Chestertown, MD - Updated, Well Positioned, and Walkable

201 Birch Run Road in Chestertown offers a compelling blend of updates, outdoor living, and walkable lifestyle—all set on a quiet cul-de-sac with views of the Chester River and close proximity to Washington College, shops, restaurants, and parks.

Thoughtful Updates

This home has been improved where it counts. In 2021, updates included joist work, flooring, crawl space encapsulation, and rear fencing, creating a strong foundation for long-term ownership. In 2025, the rough cut cedar siding was freshly repainted, enhancing both durability and curb appeal.

Indoor-Outdoor Living

The property is designed to be enjoyed. A private courtyard with a water feature offers a quiet retreat, while the spacious, partially shaded backyard with deck and…

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Coldwell Banker International Awards 2025 - International Presidents Circle

2025 was a year highlighted by growth and successful execution for my business here on the Eastern Shore of Maryland. Each year Coldwell Banker announces its highest producing agents worldwide and I am proud to announce that much like in 2024, not only am I our office's top producer but I am also recognized as one of the top 4% of agents internationally. Every sale for me represents either a new relationship or growing relationship here on the Eastern Shore. Whether you are interesting in improving your quality of life by buying here or would like to maximize your return by selling with my representation, I am here for you via phone at 443-480-4275 or email at murphy@cbchesapeake.com.

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Effortless One-Floor Living in Chestertown – 204 Rolling Rd

Effortless One-Floor Living in Chestertown – 204 Rolling Rd Comfort, Convenience, and Chestertown Charm

Located just minutes from downtown Chestertown, 204 Rolling Rd is a beautiful example of how modern comfort can blend seamlessly with Eastern Shore lifestyle. This three-bedroom, two-bath ranch-style home offers nearly 2,300 sq ft of thoughtfully designed living space — all on one level — making it perfect for anyone seeking low-maintenance living without sacrificing style or space. Spacious Living, Inside and Out From the moment you walk in, you’ll notice how bright and welcoming this home feels. The open flow between the living, dining, and kitchen areas creates a warm, connected atmosphere that’s perfect for entertaining or relaxing with family.

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Historic Elegance Meets Eastern Shore Living — 105 High Street, Chestertown, MD

A Landmark Home in the Heart of Chestertown’s Historic District

Few homes capture the spirit of Chestertown quite like this. Built in 1863, the residence at 105 High Street stands as a rare opportunity to own a piece of Eastern Shore history — thoughtfully restored for modern living. This five-bedroom, four-and-a-half-bath Victorian combines 19th-century craftsmanship with 21st-century comfort. From the moment you step inside, you’re greeted by soaring ceilings, intricate millwork, and a grand three-story staircase that defines the home’s timeless character.

A Blend of History and Modern Comfort

Every detail tells a story. The chef’s kitchen has been fully updated with stainless appliances and elegant finishes, offering the perfect…

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Just Sold - 101 S. Mill Street

101 S. Mill Street is on a quiet block just around the corner from the shops, galleries, and restaurants of Chestertown's Historic District and just 3 blocks from the waterfront promenade. The spacious rear yard with hobby shed is a gardener's delight. Historic charm with a modern floor plan is the theme here. This seller was able to quickly prepare, market, and sell his property for over asking price in the first week.  If you are thinking of buying in Chestertown please make sure to utilize the community pages on the website as a resource. If you live in Chestertown and are considering selling or just want to know how much your home could currently sell for, please visit my seller page for a private consultation.

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Just Sold - 12440 Woods Road

This amazing contemporary with sweeping views of Still Pond Creek in Worton just sold for over asking price and was only on the market for several days. This area of Kent County provides peace and tranquility with high banks alleviating flood concerns and houses that are perched high up providing incredible sightseeing. Wildlife are abundant here making it perfect for nature enthusiasts. Still Pond Creek itself provides great opportunity for boaters as well as it dumps directly into the Chesapeake Bay. This means that here you can leave your protected dock on the calm creek and be in vast open waters for fishing or sailing within minutes. The garage and updated dock were other great benefits of this property as life on the Eastern Shore comes…

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New Listing - S. Mill Street downtown Chestertown

Lovely home, c.1890 is located in the heart of Chestertown’s historic district and is just a short stroll from the Chester River Walk, Fountain Park, shops, dining and walking trails. Every modern-day amenity has been incorporated into this lovingly renovated home while preserving the original charm. Skylights and windows let in an abundance of natural light to showcase the lovely heart pine floors and detailed millwork. The home spans three levels and greets owners through a gracious foyer opening to the library with its reading nook bookcase and fireplace. The first floor open design also features a well-appointed kitchen, breakfast room, dining room, living room and two powder rooms. The second floor is designed with two ensuite…

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Sold - Chestertown Waterfront Home | Maryland Eastern Shore

Sold - Enchanting Eastern Shore waterfront residence nestled on 56-acres on Davis Creek in Rock Hall. Expert craftsmanship and style distinguish Winding Creek House. A series of pavilions are linked to create an interior of inviting, flowing spaces. Each pavilion enjoys its own river views and landscape in perfect harmony with the tranquil and naturally beautiful eastern shore setting. A charming summer house (free-standing screen porch), 100’ dock (4-ft mlw) with boat ramp, floating dock and boathouse are lovely settings to enjoy outdoor activities. Outstanding features of the home include an elevator, exquisite wood trim detail, built-in cabinetry, radiant floor heat, soaring two story living room, copper roof, granite kitchen and relaxing…

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EASTERN SHORE WATERFRONT HOME FOR SALE

Perched on the river bank, this beautiful home enjoys broad views of the Chester River and vistas of expansive marshlands. Designed by local architect Peter Newlin, FAIA, the home offers architectural elements such as a curved stair with skylight and free-standing fireplace. The open floor plan and expansive windows exude warmth and comfort accentuated by captivating river views. Set in Queen Anne’s County Maryland, the home is a 4-mile drive or quick boat ride to historic Chestertown. Founded in 1706, and home to Washington College, Chestertown is a lovely waterfront town with brick sidewalks, shops, restaurants, parks, marina, oyster bar and cafes. It is about 90 minutes from Washington, D.C. and Philadelphia.  Offered at $887,000. 

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Eastern Shore 45-Acre Certified Organic Farm for Sale

Eastern Shore 45-acre Certified Organic Farm is just 5-minutes from the Chesapeake Bay in a peaceful, private rural landscape. The farm has a pond, livestock, alfalfa and corn, and offers 35 acres of pasture, 7-acres of woods, two barns and a shed. Convenient features include two separate first floor living areas. The main living space offers a recently updated kitchen, great room, master suite, office, bedroom and family room.  Located in Kent County, Maryland, just 10-minutes from Historic Chestertown set on the banks of the Chester River. Located about 90 minutes from Philadelphia and Washington, D.C. Link to more information and photos.  Listing offered at $895,000.  

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