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4 Beds 3 Baths
This tranquil property is an oasis away from the bustle of busy life. Walk through the woods, enjoy the river from the porch, or soak in a luxurious bath overlooking the water. This home offers gorgeous views from its generous sized rooms and windows. The basement boasts Superior walls and ten-foot ceilings, just waiting to be transformed into extra living space. A cathedral ceiling and wood burning fireplace add character and charm to the family room. Outdoor living space includes a screened-in porch and deck, perfect for entertaining, or watching the wildlife in the woods and on the river. Heated floors keep toes warm in the owner suite bathroom, and the walk-in closet has built-in cubicles and shelving that provide ample space for your most prized belongings. Gutter guards make maintenance a breeze. The outbuilding provides ample space for storing equipment, or for tinkering around. Just a hop-skip-jump away from Middletown, and an easy commute to Wilmington and Philadelphia. Offers contingent on seller finding a property, or have a flexible settlement date, giving time for seller to find a property. Owner has maintenance agreement for driveway. In a rural setting; owner has dogs, cats and a caged bird on premises.

14639 John Peel Rd, Galena

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact: (410) 885-2200

1 Baths
A unique opportunity! This charming brick building was originally built in the 1800s as a chapel named Mowbray Chapel, eventually abandoned and then the interior was completely rebuilt in 2021 with electric, utilities, a new well and septic. A SIMPLY STUNNING light filled space that has been used as a residence and entertaining venue. Completed with the highest quality of materials and a brand new kitchen, full bath room and laundry room as well as a gas wood stove yet blended with the large windows, gorgeous brick walls, high ceilings and substantial woodwork. A true blend of old world elegance and modern amenities. Nestled among the mature trees on a 3+ acre property, there is also good outdoor space with a lawn, woods and a pond combined to offer spectacular outdoor areas year round.

5179 Quaker Neck Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

6 Beds 7 Baths
Gibraltar is a stunning 6 bedroom masterpiece built circa 1995 at a “then” cost of two million dollars. The very open floorplan has ceiling heights from 9 feet to 22 feet. Primary bedroom suites on both upper and main floors, both with jacuzzi tub, separate shower, double sinks, and heated bathroom floors. Elevator and level stone walk to front door allow ease of access, floating marble staircase in 43 foot wide heated marble entry way. The three floor to ceiling stone fireplaces have gas inserts and stone mantles. Large bedrooms with walk in closets in every room. Hardwood floors in Dining Room, Living room, and Office. Custom designed kitchen with Sub-Zero refrig, Dacor cooktop with grill, GE Monogram oven and microwave, Miele Dishwasher, U-line Beverage refrig, trash compactor, Wet Bar in Entertainment room with sink and service window to outside terrace. The pantry/laundry room with floor to ceiling cabinets, utility sink. Security system, water treatment system. Grounds are beautifully landscaped with a variety of flowers, bushes, trees and lovely stone walkways. The outdoor terrace has a built in hot tub and grill. The circular driveway presents an elegant way to enter the home. The driveway will hold at least 15 cars. The home has 3 Geothermal HVAC systems with 7 thermostats. Three car side entry garage. Gibraltar is being sold in “As Is” condition. Any inspections are for informational purposes only.

14079 Crataegus Ct, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact: (410) 885-1606

3 Beds 3 Baths
Nestled on a little over 2 acres, this charming home has had many wonderful updates throughout! The large, screened-in front porch will be the perfect spot to entertain guests or drink your first cup of coffee each morning. The main level of the home is bright & airy, and features a living room, full bathroom with shower, laundry/mud room, bedroom and gorgeous kitchen. The kitchen updates include modern cabinetry, upgraded stone countertops, stainless steel appliances and large island. The primary suite is just up the stairs, and has a cathedral ceiling, office area (or maybe your new walk-in closet!), and stunning bathroom. Also located on the 2nd level is a fully updated hallway bathroom and additional bedroom. The top floor features a large bonus space, just waiting for you to design for your family room, craft/hobby room, or office. The Chestertown area feels tucked away from it all, with beautiful farm and forest views along with your commute home. Looking for a delicious meal or sweet treat? Consider visiting Get the Scoop for a sundae, Waterman’s Crab House for your crab fix, Java Rock for a coffee, or maybe enjoy the outdoor dining at Harbor Shack. There are plenty of marinas nearby if you are an avid boater, or maybe take classes at the Delmarva Sailing School if it is a hobby you have been wanting to get into! THE SELLER JUST REPLACED THE WHOLE ROOF AND MORE. Sale is As-IS,

8891 Georgetown Rd, Chestertown

Listing courtesy of Caprika Realty. Contact:

6 Beds 9 Baths
Can your investments pay these dividends. Sassafras River Compound uniquely centered in between New York City, Philadelphia, Baltimore and Washington DC. Less than one hour from Philadelphia International Airport. 17 bedrooms 16.5 baths, 1900's renovated Manor house with spectacular down river views and summer sunsets. Find your favorite resting spot on the dock, the Manor house the Cottage, Pool house, Guest house or in the Barn tavern. Perfect location for plenty of water sports, Water skiing, Wakeboarding, Sailing, Paddle boarding and fishing. Just minutes by boat to Georgetown Harbor, with 5 restaurants. Must see to appreciate, but make sure you block out enough time to see all this Upper Eastern Shore gem has to offer.

32180 Wilson Point Rd, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

3 Beds 2 Baths
Price Improvement: Welcome to Hepbron's Choice c.1770 aka. WILMIL Farm. This fabulous Eastern Shore estate is nestled on 18 acres in the northwest portion of Kent County Maryland. This property has been lovingly owned by the same family since 1963. Hepbron's Choice is a rare opportunity to acquire a totally restored/renovated and immaculately maintained piece of history. Originally part of a 200 acre tract of land, the long lane leads you through open meadows and gracefully between two serene ponds, one of which has a fountain. The drive continues to capture your attention with the grace of the main residence elegantly standing on a slightly elevated part of the land. Enhanced with a large lighted flag pole, lovely mature trees (one from the Wye Oak/ Maryland's former state tree), beautiful gardens and the third large pond on the western side that offers amazing sunsets. This 18th century three-story brick home is an amazing piece of Eastern Shore History. Featured in the book, Historic Houses of Kent County published by the Historic Society of Kent County in 1998. The homeowners selectively hired local talented craftsmen over a 5 year renovation period. Historical colors were used, inspired by American History and the details are too numerous to mention. The pictures and video speak for themselves. Meticulous care was taken to recreate a kitchen honoring the historic past. With exposed original beams and custom made antique style cabinets that are truly one of a kind. Cooking will be a joy with the beautiful soapstone counter tops, a Wolf stove top and Sub-Zero refrigerator. Talk about details, the beautiful monumental open hearth fireplace with a herringbone pattern is guaranteed to be a conversation piece for all who gather. The backyard is just as lovely as the front with mature trees, lush lawn, a brick patio, one silo remains and two outbuildings that complement the home. The larger of the two features a recreation room, 3 car garage with finished interior, and a loft for storage. The other with one car space, workshop, and a fabulous screened in porch to watch the sunset over the pond. The perfect setting for a family crab feast and watching the waterfowl/wildlife. Just minutes from where the Chesapeake Bay meets the Sassafras River, a quick drive or bike ride will lead you to Betterton Beach. Venture into Chestertown, a lovely waterfront town that is home to Washington College. Residents and visitors alike enjoy the restaurants, farmers market, parks, annual festivals, and river cruises. Located about 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing of this gem today.

12807 Still Pond Rd, Still Pond

Listing courtesy of Taylor Properties. Contact: