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

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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Eastern Shore Historic Bed & Breakfast for Sale | Brampton Inn | Chestertown, MD

Savor the rich history of Brampton Inn. Set on 20 acres, the beautifully restored 1860 Eastern Shore manor house offers gracious hospitality and 13 ensuite refined lodgings in both the Inn and other cottages on the property. The Inn, a Select Registry property and rated #1 on Trip Advisor, is conveniently located just 2-miles from historic Chestertown. Brampton is a strong, viable business and is offered by its owner of over 30 years as a turnkey operation. Also for sale is an adjacent home built in 2003 set on 10-acres and an additional 5-acre parcel. The property is being offered for $2,495,000.  Link to photos and information  Brampton Info 

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Eastern Shore Waterfront Retreat | Foreston Rd | Richard Budden, Realtor

Eastern Shore waterfront retreat is privately sited on Mill Creek. Designed with cedar exterior and interior, the single floor home offers a casual ambiance with great room and large windows with water views. A new roof was installed in 2013. The dock, new deck, hot tub and floating dock invite outdoor living. Enjoy historic Chestertown with its River Walk, Washington College, shops and dining.  Foreston Photos & Info.  Offered at $521,000. 

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