Property Listings

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

View additional photos »

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

COMING SOON! 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

View additional photos »

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

A beautiful setting on Grays Inn Creek - this home features a large private dock as well as a boat ramp/launching area. The house is situated on 1.11 acres on a wonderful, peaceful creek located just around the corner from the mouth of the Chester River and the Chesapeake Bay. Enjoy the best sunsets over dinner on the side patio. Ample lawns maximize views of the creek; gorgeous spot for boating, birdwatching, fishing, crab feasts, or simply enjoying the waterfront. It could use some updating, but it's solid, and the location makes it a very worthwhile effort. Just a short drive into Rock Hall, yet a very peaceful property on the creek. Just under two hours from Philadelphia, DC, South Jersey, Baltimore; even closer to Wilmington.

Price: $850,000

View additional photos »

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

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

View additional photos »

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

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

View additional photos »

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

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

View additional photos »

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

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

View additional photos »

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

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

View additional photos »

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

Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. 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: $212,000

View additional photos »

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

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

View additional photos »

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

<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

View additional photos »

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

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

View additional photos »

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

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

View additional photos »

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

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

Price: $349,000

View additional photos »

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