SPECIAL ADVERTISING SECTION
Vice President | TTR Sotheby’s International Realty
For Courtney Chipouras, real estate is deeply personal. Born and raised in Rock Hall, she has built a career rooted in deep local knowledge, long-standing relationships, and a genuine appreciation for the Eastern Shore lifestyle. As Vice President with TTR Sotheby’s International Realty, Courtney represents buyers and sellers across Kent, Queen Anne’s, Talbot, and surrounding counties, with a particular focus on waterfront and water-access homes.
With an MBA and nearly two decades of executive sales leadership prior to real estate, Courtney brings a strategic, results-driven approach to every transaction. She is consistently recognized as a top-producing agent, trusted by clients for her market insight, disciplined negotiation skills, and ability to navigate complex deals with clarity and confidence. Her expertise spans everything from legacy waterfront estates to primary residences and weekend retreats.
Beyond transactions, Courtney is deeply invested in the communities she serves. Through her platform My Chesapeake Home, she highlights the people, places, and experiences that define life on the Shore—local businesses, seasonal traditions, and the everyday moments that turn a house into home. She is also actively involved in regional philanthropic and civic efforts, reinforcing her commitment to the area’s long-term vitality.
Known for her professionalism, discretion, and relationship-first philosophy, Courtney approaches her work with a simple belief: the most meaningful results happen when clients feel understood, informed, and well represented—every step of the way.
mobile 410-200-1224; office 410-673-3344; courtney@mychesapeakehome.com; mychesapeakehome.com
