Eastern Shore of Maryland Real Estate Blog - Eastern Shore Real Estate | Property for Sale | Murphy O'Neill Realtor

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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Historic Radcliffe Mill in Chestertown | Flex Complex on 2.3-acres

RECENTLY REDUCED !  Radcliffe Mill, located on the Eastern Shore, dates back to 1891 and is on the National Register of Historic Places. The beautiful design and restoration of the flex complex was completed in 2007 and is comprised of the 4-story mill building and the annex/seed house. It is set on 2.3-acres next to Radcliffe Creek. The main mill building features a reception area with an elevator leading to business offices and there is also a restaurant on the main level. Across the parking lot, Radcliffe Studios is located in the Seed House and offers a yoga studio, cafe, and several small wellness businesses. Property amenities include a 61-car park, loading dock and an original grain elevator.  

Dating back to 1706, Chestertown is set on the…

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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 Cottage for Sale | N. Kent St.

Charming Eastern Shore Home - Built in 2011

New Listing - Richard Budden, Realtor

Eastern Shore cottage style home was built in 2011 and is nestled in the Chestertown Historic District. The home offers off-street parking and a finished basement. Convenient location is a walk away from Washington College, the Chester River Walk and downtown Chestertown shops, galleries, restaurants and cafes. Well cared-for home has an open floor plan invoking a casual ambiance. The bright, spacious kitchen has countertop seating and a dining area that opens to the deck and a peaceful view of woods and plantings. Link to more information and large photos.  Offered at $342,000.  

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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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Eastern Shore Renovated Home | One block from the Chester River

Eastern shore home is just a block from the Chester River and a walk away from historic Chestertown’s river walk, shops, dining and Washington College. Recently remodeled home offers updated kitchen, whole house generator, and guest suite. The separate studio in the backyard is a fun getaway decorated with original paintings and slogans. An inviting sun porch overlooks the private backyard with lovely perennial gardens. Located in Queen Anne’s County near marinas and kayak launch.  View more info and photos.  Offered at: $425,000.

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Eastern Shore Farm with 54-acres | Property for Sale

Beautiful Eastern Shore Farm near historic Chestertown 

Eastern shore farmhouse, c.1890 offers beautiful 54-acre rural setting with large stocked pond. Updated in 2004, the vinyl clad home with first floor master suites has original wood detail creating a warm and inviting ambiance with pastoral views. Property is ideal for hunting with 28-acres tillable and 10-acres of woods. Just 15-minutes from historic Chestertown with river walk, shops and dining. Offered at $840,000.  More Photos & Info 

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Eastern Shore Waterfront Farm for Sale | Richard Budden, Realtor

Quintessential Eastern Shore Waterfront Farm is set on 42-acres with 690 ft. of water frontage and long views of Langford Creek. Inviting tree-lined drive leads to the lovely, well-maintained home, c.1800. Property features rip-rap shoreline, 33-tillable acres, outbuildings and garage. Enjoy the local wildlife, hunting or water activities. Adjacent 11-acre private waterfront lot is also available.  Property is offered at:$1,975,000.  Link to more Quaker Neck info

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Eastern Shore Waterfront Home for Sale | 23-Acres in Cecil County

Waterfront home with private setting of 23.5-acres is located on Mount Harmon Plantation in Cecil County. Architect-designed home with waterviews from every room is in perfect harmony with the natural surroundings. Includes deeded slip at community dock.

Inviting home features an open design with radiant floor heat and wood burning fireplace. Tranquil setting to enjoy local wildlife or kayaking on the creek. Offered at: $650,000  More photos & Info 540 Mt. Harmon Rd.

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