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Explore Our Properties
JUNE 2026 Newsletter

JUNE 2026 Newsletter

DISCOVERING WHERE YOU BELONG - LET US HELP YOU FIND YOUR DREAM HOME!


Offices in Queen Anne's, Talbot and Kent Counties

FEATURED LISTINGS

ACTIVE UNDER CONTRACT

2238 Pig Neck Road

Cambridge, MD 21613


$1,495,000


Rare opportunity in Dorchester County to purchase 108 +/- acres on Pig Neck Road just outside of Cambridge. Estimated 93 +/- acres tillable with 11.9 acres +/- acres woodland. Gorgeous old home in need or major repair or tear down. Value is in the land only. Numerous outbuildings, 20 x20 garage is newer and in good shape. Please enter home at your own risk and call local health department and planning and zoning for potential uses of property.

ACTIVE UNDER CONTRACT

115 Congressional Drive

Stevensville, MD 21666


$1,425,000


This waterfront home rests on the banks of Price Creek, a protected waterway leading to the Chesapeake Bay. Offering 4 bedrooms and 3 full bathrooms, the home features two spacious primary suites, each with en-suite baths and walk-in closets.

ACTIVE UNDER CONTRACT

1719 Harbor Drive

Chester, MD 21619


$1,395,000


Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout.

PENDING

Lot 4, Finley Creek Drive

Centreville, MD 21619


$1,053,900


Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

106 Queen Street S

Chestertown, MD 21620


$865,000


Currently operating as one of the most successful Airbnbs in the area with a strong rental history ($32K in bookings last year!), this property offers the best of both worlds--an ideal vacation home and a turn-key income-producing investment. Furniture is negotiable.


127 Pleasant Springs Drive

Centreville, MD 21617


$749,900


Set on 4.0 picturesque acres, the property includes 2.1 acres owned plus an additional 1.937 acres under a 99-year lease, with an invisible dog fence already in place. A welcoming front porch overlooks a freshly manicured, park-like landscape featuring perennial gardens, a dedicated herb garden, and a full fruit orchard, creating a serene and private setting.

ACTIVE UNDER CONTRACT

201 Beachside Drive

Stevensville, MD 21666


$699,990


This home offers flexible living space in a water-privileged community and a lifestyle that's hard to beat. Set on a generous 0.8 acre corner lot directly across from the Bay, this 4-bedroom, 3-bath home delivers space, scenery, and access to the water in one great package.

441 Eagle Manor Drive

Church Hill, MD 21623


$685,000


House in picture is to be built. This floor plan is a 3-bedroom 2.5 bath layout. Finished bonus room upstairs would make great home office or craft room. Unfinished basement for even more space. Upstairs has a separate laundry room with cabinets and countertop. 

132 Deep Shore Road

Denton, MD 21629


$679,000


An inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons.

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ACTIVE UNDER CONTRACT

1033 Avalon Court

Stevensville, MD 21666


$659,900


Nestled on a quiet cul-de-sac in one of Kent Island's most desirable neighborhoods, Mayfair Glen. This beautifully maintained home offers a perfect blend of comfort, space, and everyday livability, all just minutes from shopping, dining, schools, and an easy commute to Annapolis, DC, and Baltimore.

6984 Bluebird Hill Place

Hughesville, MD 20637


$559.900


Spectacular Views on 3 acres. New carpet downstairs with open floor plan. The finished basement offers even more living space. Ideal for home theater, gym or guest suite.

ACTIVE UNDER CONTRACT

103 Meadowcroft Drive

Centreville, MD 21617


$555,000


Welcome to 103 Meadowcroft Drive in the highly sought-after Northbrook community on Maryland's Eastern Shore -- where charm, comfort, and thoughtful upgrades come together beautifully. From the inviting covered front porch to the exceptional curb appeal, this home makes a memorable first impression.


126 Meadowcroft Drive

Centreville, MD 21617


$539,000


A beautifully updated 5-bedroom, 2.5-bath home tucked in one of Centreville's most desirable neighborhoods. With a brand-new roof within the last few years and newer dual-zoned HVAC units, this spacious home offers modern comfort, low maintenance, and peace of mind from day one.

305 E Water Street

Centreville, MD 21617


$500,000


Prime Business Opportunity on High-Visibility Water Street in Centreville!

Well-established commercial property offering exceptional exposure in a sought-after location. The first floor features a large retail, office, and storage space that has successfully housed a communications company for 26 years. The second floor includes a 2-bedroom, 1-bath apartment--ideal for owner occupancy or rental income.




ACTIVE UNDER CONTRACT

31729 W Edge Road

Millington, MD 21651


$475,000


Spacious waterfront rancher with pole barn--priced below appraised value for a quick sale! Appraised at $534K, this motivated seller is offering a rare opportunity for instant equity on the upper Chester River. Conveniently located with easy access to Rt. 301, making commuting to Philadelphia, Middletown, or the Chesapeake Bay Bridge surprisingly convenient while still enjoying the perks of waterfront living.

121 1st Avenue

Betterton, MD 21610


$450,000


This property truly has a little something for everyone! Spacious 4-bedroom, 2-bath rancher situated on 1.94 private acres in the charming waterfront town of Betterton. Featuring a full walkout basement, attached 2-car garage, and a 30x40' pole building, there's plenty of room for hobbies, storage, boats, workshops, or recreational toys.

108 John Patrick Drive

Stevensville, MD 21666


$439,900


This well-appointed 3-level townhome located in the amenity-rich Ellendale community, just minutes from the Bay Bridge. This spacious 1,900 estimated sq. ft. home offers 3 bedrooms, 3.5 baths, and a 2-car rear-entry garage with additional driveway parking.

The entry level includes an inviting foyer and a private bedroom with a murphy bed and full bath, ideal for guests or flexible use, such as an office.

ACTIVE UNDER CONTRACT

116 Kent Point Road

Stevensville, MD 21666


$449,000


Priced below value and featuring a brand-new roof (completed 9/24/2025), this move-in ready home offers both value and peace of mind. Additional updates include a new well pump, HVAC system, stove, and refrigerator. For added confidence, a one-year home warranty is included.

24295 Langford Road

Chestertown, MD 21620


$430,000


The classic brick rancher features over 1,800 square feet of living space with a full, unfinished basement offering endless potential for storage, a workshop, or future expansion. Inside, you'll find 2 comfortable bedrooms, a small room that could serve as dressing room, den or office, 2.5 baths, along with thoughtful details such as elegant pocket doors that enhance both function and flow. A cedar closet adds a touch of luxury while providing ideal storage for clothing and linens.

COMING SOON

24254 Mallow Drive

Preston, MD 21655


$399,000


This Log cabin rests on over 12 acres of open and wooded land that backs to the Choptank River. Access canoes, kayaks or prepare for waterfowl and deer seasons. The private lane leads to the large White Cedar Cabin with cathedral ceiling in the Great Room that offers an open floor plan. Home features hardwood floors and a separate loft for a bedroom or construction to make more. 


240 Merganser Drive

Chestertown, MD 21620


$389,000


Practically brand new and just 2 years young, this beautifully maintained home is perfectly situated in a desirable water-oriented community--offering the best of Eastern Shore living! Located in the Queen Anne's County school district and just minutes from downtown Chestertown, you'll love the convenience paired with the peaceful setting.

1010 S 2nd Street

Denton, MD 21629


$375,000


Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot water baseboard heat as backup.

29316 Will Street

Easton, MD 21601


$354,900


Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout.

Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come.

114 W Main Street

Sudlersville, MD 21668


$355,000


New construction. 2 bedroom, 2 bath rancher loaded with upgrades. Picture from previous model.

109 Wilton Road

Chestertown, MD 21620


$344,900


Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and restaurants, offering the perfect blend of peaceful Eastern Shore living and nearby amenities.

ACTIVE UNDER CONTRACT

29809 Captain Adamouski Street 15A

Easton, MD 21601


$318,000


Closing help offered!!! Welcome to your unique dream home in Hunters Mill! This "Charleston Villa" model built as a true townhouse with fireproof and sound proof walls. This is one of a kind twin, semi-attached duplex over 2600 sq ft. featuring hardwood floors, and crown molding thought the main level, granite countertops and a fully finished basement.

11167 Oak Lane

Worton, MD 21678


$288,500


Affordable, updated, and close to the water! Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. 

21245 Tanyard Road

Preston, MD 21655


$275,000


A spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.

406 High Street

Cambridge, MD 21613


$260,000


Looking for more space without sacrificing comfort or convenience? Welcome to 406 High Street - a move-in ready home offering over 2,700 square feet of living space, 5 bedrooms, and 2 full bathrooms, giving you the flexibility and room today's buyers are searching for!

Are you ready to embark on an exciting journey in the world of real estate? At Chesapeake Real Estate Associates, we invite you to discover your true passion and unlock a realm of endless possibilities for success. Our unique agent-owned model fosters a supportive and collaborative environment, where new agents can thrive alongside experienced mentors. Join our friendly, community-oriented team and experience the difference of personalized service that prioritizes trust and client satisfaction. Together, let's explore the dynamic real estate market on Maryland's Eastern Shore and turn your aspirations into achievements. Team up with us and take the first step towards a fulfilling career in real estate!


Work With Us

We live in a beautiful area on the Eastern Shore of Maryland, and we want you to experience that lifestyle as well. Call us today and we can get you started.

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