FEATURED LISTINGS

NEW PRICE

$2,200,000

7989 Quaker Neck Rd

Chestertown, MD 21620


Open House:

Sun May 17, 11:00AM-1:00PM

Sat May 23, 11:00AM-1:00PM

Sun May 31, 11:00AM-1:00PM


Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with sandy beach, and stunning new...

NEW PRICE

$1,350,000

5419 Ragged Point Road

Cambridge, MD 21613



Open House:

Sat May 30, 12:00PM-4:00PM
Sun May31, 1:00PM-4:00PM


An exceptional private retreat with approximately 1,500 feet of stunning waterfrontage, creating a rare sense of seclusion and serenity. This impressive 4,000+ square foot contemporary home is thoughtfully designed to capture panoramic water views from every room, seamlessly blending indoor and outdoor living...

NEW PRICE

$1,295,500

105 High Street

Chestertown, MD 21620


Open House:

Sat May 16, 10:00AM-12:00PM


This masterpiece is finally complete. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most...

JUST LISTED

$828,000

407 High Street
Chestertown, MD 21620


Open House:

Sat May 30, 10:00AM-1:00PM


Built in 1780/1840, Highcroft is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. More details and pictures coming soon!

ACTIVE

 $624,900

222 Mooring Circle # 126
Stevensville, MD 21620




Open House:
Sat May 16 , 1:00 PM - 3:00 PM


Welcome home to refined coastal living on Maryland’s Eastern Shore in this beautifully designed 3-bedroom, 3-bath home located in the premier 55+ community of Bay Bridge Cove in Stevensville, Maryland. This lovely and well-maintained home was built in 2022 and offers 2,074 square feet over two levels. The home blends light-...

JUST LISTED

 $499,000

109 Flintstone Drive 
North East, MD 21901





Spacious and beautifully updated 4 bedroom, 3.5 bath home with a finished walkout lower level offering exceptional flexibility for multi-generational living or guest space. The lower level features a complete in-law suite with a possible 5th bedroom, living room with slider leading to walk-up stairs, full kitchen, and full bathroom with private access possibilities. The main level offers...

NEW PRICE

 $499,000

4 Hidden Hills Court

Seaford, DE 19973


Open House:
Sat May 16, 2:00 PM - 4:00PM


Welcome to the desirable Rivers End community, where lifestyle and location come together. Residents enjoy a community fishing pond, recreational area, and basketball courts, along with neighborhood events and the convenience of golf cart–friendly streets...

COMING SOON  $425,000

6202 Rock Hall Avenue

Rock Hall, MD 21661


Open House:

Sat, May 30, 10:00AM-12:00PM


This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with...

NEW PRICE

 $419,900

103 Trafford Drive

Chestertown, MD 21620

Tastefully updated 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places for modern convenience and classic charm. A brand new kitchen, crown and baseboard moldings, tray ceilings, wonderful new oak ...

NEW PRICE

 $379,000

104 Main Street

Betterton, MD 21610


Open House:

Sun, May 24, 11:00PM-1:00PM


Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second...

COMING SOON

 $384,000

23416 Cloquet Road
Chestertown, MD 21620



Custom-Perfected Home with Luxury Finishes — Without the Luxury Price. This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches.Step inside to discover modern farmhouse ...

NEW PRICE

 $309,999

16 Willis Avenue
Easton, MD 21601


Open House:

Sat, May 16, 3:00 PM-5:00 PM

Sun, May 17, 12:00 PM-2:00 PM



Charming 3-Bedroom Rancher in an Ideal Easton Location!Nestled in a prime Easton location, 16 Willis Avenue offers the perfect combination of comfort, convenience, and charm. This well-maintained 3-bedroom, 1-bath rancher is ...

CBC NEWS

COUNTY SPOTLIGHT: Discover Kent County, MD


Where historic waterfront towns, scenic Chesapeake Bay views, and a relaxed Eastern Shore lifestyle come together. From Chestertown’s rich colonial heritage to the boating community of Rock Hall, explore why so many buyers are drawn to this unique corner of the Shore. Whether you're searching for a waterfront retreat, country estate, or small-town living, our local experts are here to help you find your perfect place.

Ready to explore all that Kent County has to offer?



The Maryland Eastern Shore housing market is sending mixed signals. Buyer demand remains active across many local communities, yet some home prices are beginning to soften as affordability pressures, inventory changes, and evolving buyer behavior reshape the market.

In this week’s edition of The Real Estate Market Pulse, we take a closer look at why strong demand isn’t always translating into rising prices — and what these local trends could mean for buyers, sellers, and homeowners moving forward.


Tune in for insight into what’s really happening across the Eastern Shore housing market and how to navigate today’s changing conditions with confidence.


Selling your home and want to
know how much it's worth?

For your home financing needs,

contact Trent today.



Trent Riggs

Home Loan Consultant

Main Street Home Loans

NMLS #2143938

Phone: 410-490-7061

triggs@mainstreethl.com

www.mainstreethomeloans.com

Chestertown Office 

114 S Cross Street,

Chestertown, MD 21620

410.778.0330 | 410.885.2200

Easton Office 

17 N Harrison Street

Easton, MD 21601 
410.822.9000