Samantha Grimes, Associate Broker of Chesapeake Real Estate Associates, LLC

Samantha Grimes, Associate Broker of Chesapeake Real Estate Associates, LLC Associate Broker, Co-Owner of Chesapeake Real Estate Associates, LLC. Your Eastern Shore Real Estate Connection, showing and selling the shore for 24 years.

Top producing agent in Queen Anne's, Talbot, Kent and Caroline Counties.
40 sales for 2025! Hello and thank you for visiting! It is my goal as your full service real estate agent specializing in the Queen Anne's County, Caroline County, Talbot County and Kent County areas, to provide you with superior service at all times. My local expertise consist of working with first time home buyers, new construction sales, subdivisions, lot/land sales and farms. As a resident of the Eastern Shore, I consider this community an excellent place to reside and would love to share with you my enthusiasm for the many neighborhoods that encompass it. I pride myself on providing unparalleled service and look forward to developing a long-term relationship with you. Please feel free to contact me if you would like to discuss how I can best assist you with your real estate needs.Cell is 410-310-6426

Thank you for all of the votes! Grateful to be selling the Shore even if at times its on the back of Stetson! Congrats t...
09/24/2026

Thank you for all of the votes! Grateful to be selling the Shore even if at times its on the back of Stetson! Congrats to the other agents in our office for also winning favorite Realtor!

🏡✨ SOLD! ✨🏡There is nothing quite like handing over the keys to first-time homebuyers! Congratulations to these amazing ...
09/22/2026

🏡✨ SOLD! ✨🏡

There is nothing quite like handing over the keys to first-time homebuyers! Congratulations to these amazing clients on purchasing their very first home. It was such a pleasure guiding them through the process and helping them take this exciting next step.

Thank you for trusting me to be part of your homeownership journey. Wishing you many years of happiness, memories, and new adventures in your new home! And no GHOSTS!

Many thanks to Erin Anderson, Realtor, Chesapeake Real Estate Associates, LLC the lisitng agent, Jennifer Dudley Title Excellence for Title and to Trent Riggs- Main Street Home Loans- NMLS #2143938 the money man, for making everything go so smooth! Congrats to all

Thinking about buying or selling? I'd love to help make your real estate goals a reality.

📞 Samantha Grimes, Chesapeake Real Estate Associates, LLC at 410-310-6426 Cell or office 410-643-4663

Love productive weekends! Client received multiple offers on this cutie and we are offcially under contract! Congrats to...
09/21/2026

Love productive weekends! Client received multiple offers on this cutie and we are offcially under contract! Congrats to my seller!

🌻 Big News in Denton! 🌻This stunning home at 7884 Laurel Lane has just been reduced to $559,900!Imagine enjoying your ow...
09/18/2026

🌻 Big News in Denton! 🌻

This stunning home at 7884 Laurel Lane has just been reduced to $559,900!

Imagine enjoying your own backyard oasis with a sparkling pool, peaceful wooded surroundings, and plenty of room to entertain family and friends. Inside, you'll find beautiful spaces designed for comfortable everyday living.

If you've been waiting for the right opportunity, this could be it!

📍 7884 Laurel Lane, Denton, MD
💲 Now $559,900

Contact Samantha Grimes today for more information or to schedule your private tour. Full Listing details below:
https://samanthagrimes.chesapeakerealestateassociates.com/properties/7884-laurel-lane-denton-md-us-21629-805283461726

📞 410-310-6426 Cell
410-643-4663 Office


If you missed the Open House on Sunday, you have another opportunity to tour this beautiful waterfront home on Cox Creek...
09/15/2026

If you missed the Open House on Sunday, you have another opportunity to tour this beautiful waterfront home on Cox Creek!

📍 1717 Harbor Drive, Chester
📅 Thursday, September 17
⏰ 5:00 PM to 7:00 PM

Come experience the stunning waterfront views, private dock, and spacious interior for yourself. We look forward to seeing you there!

If you missed the Open House on Sunday, you have another opportunity to tour this beautiful waterfront home on Cox Creek...
09/15/2026

If you missed the Open House on Sunday, you have another opportunity to tour this beautiful waterfront home on Cox Creek!

📍 1717 Harbor Drive, Chester
📅 Thursday, September 17
⏰ 5:00 PM to 7:00 PM

Come experience the stunning waterfront views, private dock, and spacious interior for yourself. We look forward to seeing you there!

Full Listng Details:
https://samanthagrimes.chesapeakerealestateassociates.com/properties/1717-harbor-drive-chester-md-us-21619-805319084832

Samantha Grimes, Associate Broker of Chesapeake Real Estate Associates, LLC
410-643-4663 Office
410-310-6426 Cell

🚨 PRICE IMPROVEMENT! Now $254,900 🚨 Almshouse ( Lot 2) Rd, Oxford, MD 21654Build your dream home on this beautiful...
09/09/2026

🚨 PRICE IMPROVEMENT! Now $254,900 🚨
Almshouse ( Lot 2) Rd, Oxford, MD 21654

Build your dream home on this beautiful 2.3-acre wooded lot between Easton and Oxford!

✔ Perc approved for a 4-bedroom home ✔ Cleared and ready for permits ✔ House plans available ✔ Private setting in a highly desirable location

Opportunities like this are rare. Don't wait! Full Listing Details: Please note price has not updated yet but it is now $254,900!
https://samanthagrimes.chesapeakerealestateassociates.com/properties/almshouse-lot-2-road-oxford-md-us-21654-805177093572

📲 Contact me today for details.
Samantha Grimes, Associate Broker of Chesapeake Real Estate Associates, LLC
410-643-4663 Office
410-310-6426 Cell

🏡🌳

09/08/2026

🌅 Imagine waking up on the water, enjoying peaceful mornings, and living the relaxed Kent Island lifestyle you've been dreaming of.......

Tomorrow, 1717 Harbor Drive in Chester, MD officially hits the market! This stunning property offers the perfect opportunity to enjoy everything the Eastern Shore has to offer while remaining conveniently connected to Annapolis and beyond.

📍 1717 Harbor Drive, Chester, MD 📅 Going Live Tomorrow

Don't miss your chance to tour this exceptional home. Click the link below for more info:
https://samanthagrimes.chesapeakerealestateassociates.com/properties/1717-harbor-drive-chester-md-us-21619-805319084832

For a personal tour reach out to
Samantha Grimes, Associate Broker of Chesapeake Real Estate Associates, LLC
410-643-4663 Office
410-310-6426 Cell

🚨 NEW LISTING ALERT! 🚨The wait is over! 🎉7464 Shortall St, Chestertown has officially hit the market, and you won't want...
09/03/2026

🚨 NEW LISTING ALERT! 🚨

The wait is over! 🎉

7464 Shortall St, Chestertown has officially hit the market, and you won't want to miss it. If you've been searching for a home that offers space, comfort, and a fantastic location, this could be the one.

🏡 Beautiful home 📍 Desirable Chestertown location 🔑 Ready for its next owner

Want a first look? Send me a message today to schedule your private showing before it's gone!

More Details:
https://samanthagrimes.chesapeakerealestateassociates.com/properties/7464-shortall-street-chestertown-md-us-21620-805293270356

📞 Samantha Grimes
Samantha Grimes, Associate Broker of Chesapeake Real Estate Associates, LLC
410-643-4663 Office
410-310-6426 Cell

Address

1563 Postal Road, Suite 2B
Chester, MD

Telephone

+14103106426

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