Property Listings

Chestertown

Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops, a first floor one bedroom apartment, as well as a spacious apartment upstairs. Back deck overlooks sweet courtyard, perfect for relaxing. GREAT location and tons of character - enjoy the Chestertown Farmer's Market year round, the Chester River just a few blocks away, shops and restaurants right down the street - you cannot beat this Historic District location and opportunity. Seller has removed plaster walls downstairs and updated the electric. Other updates include: exterior painting, new metal roof and a new deck with entry to second floor apartment.

Price: $349,000

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Chestertown

COMING SOON-This exquisitely renovated 1800s home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory. No expense has been spared in selecting the finest finishes and materials for this renovation and it extends beyond the interior, with the creation of an outdoor oasis. This meticulously landscaped gardens and charming patio provide a private retreat right in the heart of Historic Downtown Chestertown. Chestertown is conveniently located on Maryland's Eastern Shore, less 80 miles from Washington DC and 90 miles from Philadelphia

Price: $950,000

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Chestertown

COMING SOON-This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience. Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just two blocks from the Chester River waterfront. Chestertown is conveniently located on Maryland's Eastern Shore, less 80 miles from Washington DC and 90 miles from Philadelphia

Price: $625,000

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Worton Creek

COMING SOON-Park like setting with natural beauty all around you, take a quite day with very nice outdoor den . Watch the herons, eagles, ducks and geese search for food or take a leisurely kayak cruise down Mill Creek to the Chesapeake Bay. Conveniently located a short distance from Worton Creek Marina, Restaurants, Resort Style Marinas, Historic Chestertown, Parks and much more. Chesapeake Landing Offers water access with 2 marinas, boat slips and docks. A perfect location to keep for a weekend away on the beautiful Eastern Shore or primary residence.

Price: $715,000

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Rock Hall

Welcome to McKinleyville Road. Situated on a beautifully landscaped half-acre, just a few steps from the Rock Hall Yacht Club. This is a gorgeous architect-designed home with a spacious, open and flowing floor plan. Gleaming wood floors throughout, soaring cathedral ceilings and a stately wood-burning fireplace. The primary bedroom suite is on the first floor with an attached bath that will pamper. There is a huge screened porch and a wrap around deck, all facing peaceful, private woodlands. Two more guest bedrooms upstairs share a large bath. There is also an attached two-car garage with room for a workshop. Just minutes to multiple marinas, public boat launches, and downtown Rock Hall with many popular restaurants and an acclaimed jazz venue. Chestertown's Historic District, with a year-round farmer's market, is just a short drive away as well. Come see this stunning house nestled perfectly in the country - you won't regret it.

Price: $585,000

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Chester River

Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This condominium embodies the ideal waterfront living experience. Located in the heart of historic Chestertown, this unique property includes off-street parking and provides the convenience of walking into town for dining and shopping. Situated on Maryland's scenic Eastern Shore, it's less than 85 miles from Washington D.C. and Philadelphia, making it a perfect meeting spot for those in the Mid-Atlantic region.

Price: $750,000

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Rock Hall

This classic Rock Hall home has been beautifully upgraded with interiors that will make you feel pampered.  Bright and welcoming with high-end finishings, granite counters, stainless steel appliances and room for entertaining. The primary bedroom and bath are located on the first floor for easy living. The primary bedroom offers a large closet and a separate entrance to the backyard. Three more bedrooms and a full bath upstairs for guests and family. Enjoy meals or a drink on the screened-in porch! This in-town property offers a surprising amount of space and privacy. The yard is completely fenced, making it safe for your pets.  There is a brand new shed with electric, which would make a great little workshop. Fantastic location,  steps away from multiple restaurants, marinas, shops and the Chesapeake Bay. Out of the flood zone. Town water and sewer. Just under two hours from Phila., DC, South Jersey, Wilmington or Baltimore.  Furnishings are included - all you need to do is unpack your bags, relax and enjoy the best of Rock Hall in this turn-key home. This home was completely restored and updated in 2022, more recent updates include, new washer/ dryer, fenced yard and a new shed with thermal wrapping and electricity.

Price: $470,000

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Kentmore Park

Kennedyville

Coming Soon!! Kentmore Park Cottage carefully improved. Four bedrooms and three baths. Spacious kitchen. Large great room with hardwood flooring and many windows for light and excellent ventilation. Wood burning fireplace. Modernized kithchen with hickory cabinets, granite coutertops, stainless steel appliances and tile backsplash. Owners suite over great room. Guests quarters on opposite side of the home. Large covered screened porch off the kitchen looking out to the private rear yard. Open deck off the screened porch. Three bay garage below the deck and the entrance to the partial basement. Tasteful landscaping with abundant shade trees. Easy walk to the community areas. The Little pier and the Big pier. Minutes from Galena for quick shopping and dining. Close to rt 301 for sites north and south. Easy drive to Middletown Delaware for just about anything. Close to Chestertown for an historic experience, casual and fine dining, arts and Washington College. Perfect primary or second home. Come visit.

Price: $535,000

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Galena

Discover the rare opportunity to own your very own private 48 acre parcel that currently includes an airstrip and water access to the Sassafras River. Choose a location for your home enjoy and enjoy a very private haven on Maryland's eastern shore. Very easy access to points north (Wilmington, Philadelphia, New York) and south (Annapolis, Baltimore, Washington, DC) just 58 miles with no red lights to Philadelphia Airport .

Price: $598,000

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Galena

Lot 87 & 88. Build your Dream Home in Water Oriented Community. Shorewood Estates is a sought after community with it's own community dock, beach and marina. Located near marinas, waterfront restaurants, close to major highways, points north and just minutes away from Middletown, DE with plenty of restaurants and shopping.

Price: $87,500 Each

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Chestertown

Lot 3 located at the midway point of Fairway #10, a perfect spot to enter the back nine and head to the club house for lunch or dinner (membership required) Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.

Price: $150,000

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Chestertown

Location (3 fairway lots available), Location (minutes from historic Chestertown), Location (easy access to pristine waterways of Maryland s eastern shore). Two other interior lots available including two corner locations. Lot 4 overlooks two greens on on hole #10 the other on # 5 with fairway boarders on two sides. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the areas finest builders

Price: $175,000

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Rock Hall Harbor

Chesapeake Bay

Waterfront rental with a boat slip! Fantastic views every season. Spring, summer & fall boat activity and calm winter vistas. Two bedrooms and two full bathrooms, as well as two half baths. The third floor can be additional sleeping space, and has a deck with a birds eye view. The main level is open living space, great for entertaining! Enjoy all meals on the deck. The best part is the fireworks view on the 4th of July. Best seats in town! Bring your boat and start enjoying the Rock Hall lifestyle. 1-year lease, rental comes fully furnished, renter responsible for utilities, pets on a case-by case basis with deposit.

Price: $5,500/ Month

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Chester River

A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland’s scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. 5 Units ranging from 1-2 bedrooms

Price: Starting @ $385,000

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Fairlee

Rare opportunity for a garage/ workshop in a great residential location. Spacious, situated on a triangular shaped half acre lot. Check out the many possibilities for this property. Great investor opportunity in a beautiful neighborhood. Buyer to confirm with Kent County Planning & Zoning regarding any plans to build or convert to residential home.

Price: $70,000

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Chester River

Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasure. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops, restaurants and parks..

Price: $848,000

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Hunter's Run

Galena

Beautiful sought after home in Hunters Run on 3/4 acre. First floor primary suite, hardwood through out foyer, dining room, gourmet kitchen with granite countertops, and 2 story family room, with overlook, perfect to cozy up to by the fire and large screened in tiled porch to relax and enjoy in the summer. Second floor offers 3 more bedrooms, full bath, and large bonus room. Additional oversized garage with ample storage and whole house generator. Located near marinas, water front restaurants and close to major highways, just minutes from Delaware with lots more restaurants an shopping.

Price: $548,000

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Pond Creek

Chesapeake Bay/Elk River

Build your dream home on this slice of paradise! Take advantage of the stunning sunsets this 9+ acre waterfront lot has to offer. Wonderful opportunity own 400+ ft of waterfrontage on Pond Creek in Earleville. Located in the community of Sunset Pointe with access to the community beach and dock and direct access to the Chesapeake Bay.

Price: $549,000

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Sassafras River

Need a weekend getaway spot with income to support the mortgage and expenses or downsizing and looking some side hustle income or strictly and investment property. This completely renovated home and cottage, with income producing billboard along with harbor water views of the upper Sassafras could be the perfect fit for you. Keep your boat at the Marina and have access to all of the marina amenities including pool , walk to the four restaurants in the harbor. Commercial zoning provides limitless uses, just configure this unique property for fit your needs and desires. Very easy access to points north and south. Sale includes sale of three parcels, Tax ID 0801005596 ( 2 bedroom home), 0801011685 (billboard), 0801012703 (cottage with loft)

Price: $350,000

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Swan Creek

Chesapeake Bay

Bayfront building lot - just over a third of an acre. Magnificent Chesapeake Bayfront views, with views of Swan Creek in back. Federal permission has been granted for a 200 ft long, 6 ft wide pier with a T-dock at the end. There would be approx 5 ft mlw at end of pier. Buyer to obtain LOCAL PERMITS for dock. Survey is available upon request. Town water and sewer is already installed on site. Very close to marinas and restaurants; there is a private marina just across the street. Under two hours to Phila, South Jersey, Wilmington, Baltimore ad DC. Build your dream home on dreamy, beautiful Lawton Avenue in the Gratitude section of Rock Hall - on the Chesapeake Bay.

Price: $750,000

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Chestertown

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Price: Starting @ $950,000

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Georgetown

Sassafras River

Rare combination of historic home and water views, with many of the benefits of waterfront without the high cost. Two decks with relaxing water views and very large yard for plenty of out door activities. Rent a slip at the marina below and enjoy all the benefits of the marina including pool, boat store, ice cream shop and local restaurants. Plenty of rooms to fit your desires or imagination.

Price: $398,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.