Chesapeake Bay Properties

Maryland's Eastern Shore is a place unlike any other — waterfront estates, charming historic towns, and a pace of life that draws buyers from across the country.

Chesapeake Bay Properties has been guiding buyers and sellers through this distinctive market for decades, with Team Lead Brian Gearhart calling the Eastern Shore home since 1983 and a full team of dedicated agents who know every community, every road, and every nuance of this region.

The Whole Shore, Covered From Easton and St. Michaels to Oxford, Cambridge, Chestertown, Stevensville, Centreville, Denton, and beyond, our team serves the full breadth of the Eastern Shore — with listings ranging from attainable first homes to multi-million dollar waterfront properties.

Search, Explore, and Connect Browse featured listings, explore neighborhood guides for every major Eastern Shore community, request a home valuation, and reach our team directly — all within one easy-to-use app built for buyers and sellers who take this market seriously.

The Team That Shows Up Clients consistently highlight one thing above all else: this team picks up the phone. Whether it's a weekend, late evening, or a complicated multi-month transaction, Chesapeake Bay Properties is there — responsive, knowledgeable, and genuinely invested in your outcome.