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Explore Our Properties
August 2026 Newsletter

August 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

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.

106 Queen Street S

Chestertown, MD 21620


$829,000


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.

132 Deep Shore Road

Denton, MD 21629


$629,000


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.

7884 Laurel Lane

Denton, MD 21629


$569,900


Offered for the first time, this custom-built home is nestled on 2 private acres in the highly sought-after water access community of Forest Landing, conveniently located between historic downtown Denton and Easton. Beautifully updated and move-in ready, this property offers 3 bedrooms, 2.5 baths, and a finished bonus room, providing flexible space for a home office, gym, playroom, or guest accommodations.

161 Greenwood Creek Road

Queenstown, MD 21658


$549,900


This house is ready for your own personal touches and repairs, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches.

126 Meadowcroft Drive

Centreville, MD 21619


$534,900


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.

812 Teacher Mitchell Road

Glen Burnie, MD 21060


$530,000


Welcome to this beautifully maintained 4-bedroom, 3 full and 1 half bath townhome in the highly sought-after Tanyard Shores community! Offering three spacious levels of living, this home combines comfort, style, and convenience in one incredible package.

COMING SOON

214 Belvedere Avenue

Centreville, MD 21617


$499,900


Discover the space, convenience, and potential this 4-bedroom, 3-bathroom Centreville home has to offer. Situated on an expansive 0.45-acre lot, this property provides plenty of room to spread out and create a home that fits your lifestyle.

6984 Bluebird Hill Place

Hughesville, MD 20637


$499,900


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.

11598 Malvern Lane

Cordova, MD 21625


$479,000


Nestled in the serene Chapel Woods subdivision, this charming traditional home offers a perfect blend of comfort and functionality. With four spacious bedrooms and two full bathrooms, this residence is designed to meet your needs for both relaxation and entertaining.

305 E Water Street

Centreville, MD 21617


$450,000


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.

12690 Peach Lane

Cordova, MD 21625


$430,000


This home shows true pride of ownership in sought-after Fike's Orchard in Talbot County, located in the Chapel School District. Situated on over an acre, this property features mature landscaping, an established vegetable garden, and a welcoming front porch with views overlooking the original farm and orchard.

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.

123 Trafford Drive

Chestertown, MD 21620


$375,000


Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.

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.

306 Caroline Avenue

Ridgely, MD 21660


$340,000


Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash.

114 W Main Street

Sudlersville, MD 21668


$324,900


New Construction. 2 bedroom, 2 bath rancher loaded with upgrades.

9126 Fairlee Road

Chestertown, MD 21620


$324,000


Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs

COMING SOON

7474 Shortall Street

Chestertown, MD 21620


$304,000


Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy.

504 Sunset Blvd.

Ridgely, MD 21660


$270,000


***Back to Active due to no fault of the Sellers. They have found the home of their choice bring us an offer!! *** This delightful 3-bedroom rancher offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy block construction and inviting layout. The cozy 864 sq. ft. interior is complemented by essential appliances, including a refrigerator, stove, washer, and dryer, making daily living a breeze.

11167 Oak Lane

Worton, MD 21678


$269,900


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.

310 Park Avenue

Federalsburg, MD 21632


$205,000


This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style.

313 Washington Street

Cambridge, MD 21613


$185,500


Unlock the potential of this duplex located in downtown Cambridge! Whether you're looking to expand your investment portfolio or generate rental income, this property offers plenty of opportunity. The first unit features 3 bedrooms and 1 full bathroom, while the second unit offers 2 bedrooms and 1 full bathroom, providing flexibility for long-term tenants, owner-occupants, or future rental income.

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!


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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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