Welcome Jill Brooks

Now Serving Chestertown, Cecil County, Chesapeake City, Warwick & the Fair Hill Area

As Coldwell Banker Chesapeake continues to grow throughout Maryland’s Eastern Shore—including Chestertown, Cecil County, Chesapeake City, Warwick, the Fair Hill area, Kent County, Queen Anne’s County, and surrounding waterfront and rural communities—we remain focused on trusted, relationship-driven real estate service.

From the historic charm of Chesapeake City along the C&D Canal to the scenic farmland around Warwick and the equestrian lifestyle near Fair Hill, the Upper Shore offers a unique blend of community, outdoor recreation, and space to breathe. Jill’s lifelong connection to the region gives clients a true local advantage—whether they’re moving across town or relocating to the Eastern Shore for the first time.

Rooted Locally, Committed to Service

Jill grew up in Chesapeake City and has stayed local her entire life. Today she lives in Warwick, Maryland with her husband, their two children and their two dogs. For the past 13 years, Jill has worked in estate management for a private company right in Chesapeake City, building a reputation for professionalism, discretion, and detail-driven service.

“A career in real estate has always been something I planned to pursue,” Jill shares. “I’m very excited that now is the time—and I truly look forward to meeting and working with everyone.”

Experience with Renovation, Resale & New Construction

Jill’s real estate knowledge is also personal. Before having kids, Jill and her husband purchased, renovated, and resold two investment properties in the area—one in Elkton and one in Cecilton. In 2020, they built their own home, giving Jill first-hand appreciation for the building process and the importance of smart planning, timelines, and budget clarity.

That mix of professional organization and real-life experience helps Jill support clients through every stage of a move—whether you’re buying your first home, upsizing for a growing family, or selling an established property with a lot of memories attached.

Real Estate for the Equestrian Community: Fair Hill & Beyond

Horses have always been a big part of Jill’s life. She grew up riding and competing, and in her 20s she was heavily involved in advocating for the aftercare of racehorses, especially Maryland-bred horses. That lifelong connection makes Jill a natural fit for clients seeking an agent who truly understands equestrian culture and rural property considerations.

If you’re exploring equestrian properties near Fair Hill, acreage with barns, or homes that offer quick access to trails and training facilities, Jill brings both lifestyle alignment and a polished, practical approach to the buying and selling process.

Family, Community & Shore Life

Jill is deeply involved in her community. She serves on her children’s school PTA as the volunteer coordinator. Outside of work, Jill loves coffee, being outdoors (when it doesn’t feel like we live in Antarctica), dogs—especially German Shepherds—watching her kids play baseball and soccer, and relaxing whenever time allows.

That authentic, down-to-earth energy is what clients often want most: an agent who is approachable, responsive, and genuinely invested in helping them feel at home on the Eastern Shore.

How Jill Helps Buyers & Sellers

Jill is a Maryland-licensed real estate agent dedicated to helping clients navigate buying and selling with:

• Clarity — straightforward guidance and transparent communication
• Confidence — informed decisions backed by local insight
• Care — people-first support from start to finish

Service areas include: Chestertown, Cecil County, Chesapeake City, Warwick, the Fair Hill area, Elkton, Cecilton, Kent County, Queen Anne’s County, and surrounding waterfront and rural communities.

Connect with Jill Brooks

If you’re thinking about buying or selling on Maryland’s Eastern Shore—or you want a trusted local resource for the Cecil County and Fair Hill equestrian lifestyle—Jill would love to connect.

• Office: Coldwell Banker Chesapeake – Chestertown Office
  114 B. South Cross Street | Chestertown, MD 21620
• Email: jill@cbchesapeake.com
• Phone: 443-566-2775
• Facebook

Please join us in welcoming Jill Brooks to Coldwell Banker Chesapeake!

Frequently Asked Questions

Where does Jill Brooks work?

Jill Brooks is a Maryland-licensed real estate agent with Coldwell Banker Chesapeake, based out of the Chestertown office.

What areas does Jill serve?

Jill serves Maryland’s Eastern Shore, including Chestertown, Cecil County, Chesapeake City, Warwick, the Fair Hill area, Kent County, and Queen Anne’s County.

Can Jill help with equestrian properties near Fair Hill?

Yes. Jill has a lifelong connection to horses and understands the equestrian lifestyle, including considerations for rural acreage, barns, and access to riding opportunities near Fair Hill.