Property Listings - Waterfront Townhomes and Condos

Bayfront condo with exceptional views, located in the heart of Rock Hall!  Beautiful open living space for entertaining, featuring a propane fireplace and bayfront balcony with awning. The eat-in kitchen features updated countertops and a Bosch electric range.  The primary bedroom has its own bayfront balcony and an updated attached bathroom. Two additional bedrooms share a full bathroom. The third-floor bedroom has a fantastic view and could be used as an office, studio, or overflow space for guests . On the ground floor, the bayfront storage room is a great space to keep fishing poles, kayak, or pool floaties to use at the condo pool! One-car garage with additional outside parking, as well as communal overflow space for guests. Tilghman’s Landing condo is a beautiful waterfront condo association! Located in the heart of everything, yet tucked away from the hustle and bustle. Enjoy the pool in the summertime and never miss a sunset on the balcony.  A sandy beach is located just outside the association, and the Rock Hall beach is just down the street. Short distance to ample restaurants, shops, and marinas.

Price: $650,000

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**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Price: $849,900

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Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern kitchen is designed to inspire culinary creativity, boasting stainless steel appliances and ample storage space. Just up the stairs you will find two large guest bedrooms, washer and dryer, and a full bathroom. The primary bedroom is located on the third level with a view of the Bay. You'll love the large private balcony overlooking the Chesapeake. The primary bathroom has a soaking tub as well as a shower, and a walk-in closet with ample space for storage. This residence is located a short stroll from marinas, a vibrant array of restaurants, and downtown shops. Easy access to festivals throughout the summer and fall, enjoy a delightful day out or a cozy evening at your favorite eatery. The charm of this location is not just limited to daytime adventures; it transforms into a magical setting at night! The best part is the unobstructed views of spectacular 4th of July fireworks, all from the comfort of your own home. This condominium offers relaxation and convenience while taking in all the charms of Rock Hall. With a focus on comfort, every corner is thoughtfully designed to cater to your needs, blending modern amenities with the natural beauty of its surroundings. Don’t miss the opportunity to make this beautiful condominium your own! Embrace the coastal lifestyle and let the Chesapeake Bay become your new escape.

Price: $545,000

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Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes. On the second floor, the spacious primary deck boasts expansive views of the Chestertown skyline and treats you to breathtaking summer sunsets—your personal oasis in this vibrant community. Just a short stroll away, you'll find the charm of Historic Downtown Chestertown and the scenic Wilmer Park, offering the perfect blend of convenience and lifestyle. Chester River Landing is a coveted water-access community offering a host of amenities, including an in-ground pool, two grilling and dining areas, and ample community space. Enjoy the large community dock with boat slips available for sale or lease—a dream for boating enthusiasts. Don't miss this opportunity to own a piece of Chester River Landing paradise!

Price: $579,000

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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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CONDO BY THE BAY - Beautiful condo with Chesapeake Bay views from every level. On a clear day, you can see the Chesapeake Bay Bridge. Decks on two levels - one from the living room and the other from the primary bedroom - for catching the sunsets and the sparkling bay. You'll love the poolside location, with views from the gourmet kitchen of the iconic Gratitude neighborhood and marina right next door. The town's sweet beach on the Chesapeake Bay is just a short distance down the street - as is a great restaurant with a tiki bar in the other direction. Multiple marinas nearby, as well as several public boat launches. Two generously sized bedrooms and baths on the third level, as well as a top level bedroom with a cute kids built-in "hideout." The ground level features a one-car garage and an extra room that you could set up as a workshop. New roof in 2020. Come see - this condo has it all for a most enjoyable Rock Hall lifestyle!

Price: $550,000

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Stately waterfront Victorian home rich in history with endless possibilities depending on your needs or desires. Original home built in the late 1800’s could be redesigned to its original grandeur. Currently the building is a six-unit multifamily property offering plenty of potential. The entire first floor and part of the lower level is a large approximately 2,700 square feet “owners’ home” that was recently renovated with top quality materials and redesigned to take advantage of the waterfront living this building offers. There are also five other units providing income and cost sharing, including a one-bedroom garden apartment on the lower level and two additional one bedroom units on both the 2nd and 3rd floors. The five apartments have separate entrances from the first-floor apartment and provide a gross monthly income of $5000. Investors will appreciate the 6-unit rental with an approximate cap rate of 5.75%. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. 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. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. There is a recently installed deep water fixed/floating dock with two new boat lifts.

Price: $1,295,000

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Completely renovated 4 bedroom waterfront condominium located in the heart of historic Chestertown. 2 boat slips, adjacent to Wilmer Park and a few block from the main commerce area of the town including shopping and restaurants. Condominium renovations include but not limited to new kitchen, new baths, hardwood floors throughout, new dock, recently replaced roof, new HVAC systems just to name a few.

Price: REDUCED! $1,398,000

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Crews Landing- a small townhouse complex with their own beach and dock located in Betterton, Jewel of the Chesapeake! End unit with conditioned Florida Room. Spacious townhouse with great views of the Bay. Boat slip with boat lift included.<br />View the property Video Below: <br /><a href="https://vimeo.com/350789290">https://vimeo.com/350789290</a>

Price: $395,000

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One of the premier units located in the front building of Crews Landing townhouse. Unobstructed view of the upper Bay. Spacious deck with a screened porch attached. Best kept secret on the Eastern shore, Betterton Beach. Boat slip with lift included, unknown condition of boat lift, no warranties as to the operation of, private beach. Let the condo association take of the the maintenance outside while relaxing taking in that beautiful view or enjoy taking a boat ride to dinner. Great location by water to venture to North East or the western shore.<br />View Property Video Below:<br /><a href="https://vimeo.com/350789290">https://vimeo.com/350789290</a>

Price: $445,000

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Exceptional 4800+ sq ft corner unit townhouse with expansive views of Swan Creek and the Bay. Elevator to the top. There are 4 bedrooms, each with an attached full bath. 4th bedroom is currently used as a professional office. Private pool. Two-car garage plus two more parking spaces. Short walk to bay-front beach. Everything customized to the highest standards; nothing left to do except move in.

Price: $795,000

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First unit to be offered for sale in Crews Landing in three years. This second row unit which has had only one owner has been impeccably maintained. Beautiful views of the Bay. Some custom cabinetry, oak floors,and balcony off mastersuite are just a few wonderful amenities. Walkway to the dock and beach or access road to drive down to the dock. Deep water boat slip with lift included.

Price: 405,000

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