Chester River Property Listings

**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 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. There is a first floor primary bedroom for one-floor living options. Upstairs, the second primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. 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. Listing Office

Price: $1,099,900

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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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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. 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: $786,900

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. 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: $765,900

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private second floor balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. 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: $753,500

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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.

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. 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: $813,900

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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.

Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. 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: $799,900

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Discover the luxury of coastal living with this masterpiece waterfront property located in a much sought-after location on the Chester River. When entering the home, you’re immediately greeted in the elegant foyer that opens to a formal dining room to the right, and an office to the left that could easily be converted to a first floor bedroom. The fully renovated chef’s kitchen features state-of-the-art appliances, a spacious island, and ample cabinetry, making it perfect for hosting both large parties and intimate gatherings. The expansive living room features a fireplace and full views of the sparkling waterfront. This meticulously renovated home features 3 bedrooms, each with an en suite bath. The second floor boasts a relaxing combination of a screened porch and an open deck spanning the full front of the house and overlooking the river. The very large primary suite, with it's pampering bath, also has an entrance to the inviting screened porch. When stepping outside, the gracious landscaping calls for you to unwind on the open deck and work on your tan, or step onto your own private dock and explore the river a bit. There is also a covered brick patio, perfect for firing up the grill and eating al-fresco. Located just minutes from local shopping and schools, this paradise offers you a life of convenience, without compromising privacy and luxury.

Price: $1,495,000

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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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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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THE COVE - 385 feet of waterfront shoreline, wrapping around two sides of this property, located in a premier boating destination. Large rancher, one-floor living on Long Cove. Very easy access from here to the Chester River and the Chesapeake Bay. The property has a rare offering of it's own wide boat ramp, along with bulkheading and dockage. Protected waters - your boat will be safe here during heavy weather. There is an adorable "boat-house" at the water's edge, perfect for storing all your water toys, decoys, or use as an art studio. The combination of an ample screened porch leading to a large deck, overlooking a beautiful lawn and water views, makes this the perfect location for fun parties or just quiet relaxing, and of course boating excursions. The house is surrounded by waterviews from the porch, the kitchen, the family room, into the primary bedroom. There is a cozy wood stove in the large den which has a cool retro "hunter's lodge" vibe. Serviced with public sewer, no septic to worry about. Would make a fantastic vacay rental. Exceptional opportunity for an active waterfront lifestyle just five minutes from downtown Rock Hall and 15 minutes to Chestertown. Just under two hours in either direction to Baltimore, Philadelphia, DC, Wilmington, South Jersey.

Price: $825,000

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Enjoy endless water views, breathtaking sunsets and easy access to the water from this four bedroom home that provides many of the highly sought after features of an Easter Shore waterfront property. This property also has a bulkheaded and rip-rapped shoreline, a blend of open lawn and mature shade trees and is in a great location by water.  Easy boating access on the Chester River with close proximity to the Corsica River, Langford Creek, or even Kent Island and just a short drive from Chestertown and Rock Hall.

Price: $945,000

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A diamond in the rough with nearly all the desired features for waterfront property. Broad expansive 180 degree southwesterly views of Langford creek, four season sunsets, protected dock and slip. Crabbing, fishing, wake boarding, water skiing, paddle boarding, sailing all in your back yard. Just a few minutes from historic downtown Chestertown and very easy access to points north, Philadelphia and Wilmington or south, Washington DC and Northern Virginia.

Price: $749,000

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10 building lots just released for sale in great water access community of Chester River Heights. Very easy access to points north and south, especially with the soon to open Middletown by-pass. Act soon to pick out your choice spot.

Price: $32,500 to $45,000

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<span>Very private 3 bedroom home in park like settling located on the upper reaches of Morgnec Creek with water access to the Chester River. Bring your boat to explore all nature has to offer, commune with eagles, herons, terns, deer, turtles and other wildlife on this lovely creek. This home offers waterfront views from nearly every room, numerous upgrades over the past few years, perfect for a weekend get away or a fulltime resident. Just minutes from historic Chestertown and with the new Middletown by-pass less than 1 hour from Wilmington and points north.</span>

Price: $589,000

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Cozy 3 bdr waterfront home with all the natural, private surroundings the eastern shore has to offer. Very easy access to more than 300 feet of bulkheaded shoreline. 2 large detached garages to store all the waterfront toys you will need to take advantage of all Langford Creek has to provide, fishing, crabbing, year round hunting or whatever you waterfront dreams desire.<br />View Property Video Below:<br /><a href="https://vimeo.com/300826586">https://vimeo.com/300826586</a>

Price: $538,000

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A spectacular waterfront location just outside of historic Chestertown providing privacy but not isolation, a blend of lawn and mature shade trees, over 200 feet of waterfrontage, private dock with a boat lift, beach, sunsets and is improved by a three bedroom home with a screened porch overlooking the water, hardwood floors, views of the river from almost every room and is situated to offer easy access from the house to the water's edge.<br />Click the Link below to View the Property Video<br /><a href="https://player.vimeo.com/video/226756065">https://player.vimeo.com/video/226756065</a>

Price: $645,000

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Beautiful building lot with broad water views and sunsets.  Fully bulkheaded, level lot close to Historic Chestertown and a county park.

Price: $349,000

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