Bailey focuses her practice on real estate matters including condominium and homeowners association development, purchase and sales transactions, financings, title and survey, and due diligence, and in corporate transactions, including joint venture formations and governance.

Previously, Bailey worked as a Staff Attorney on the Covid-19 Eviction Legal Help Project at the Central West Justice Center in Worcester, Massachusetts, as a Judicial Intern to Administrative Law Judge Neile Eisner at the United States Equal Employment Opportunity Commission in Boston, Massachusetts.

Bailey was a Systemic Lawyering Corps Member at the Covid-19 Rapid Response + Systems Summer Institute, Harvard Law School in Cambridge, Massachusetts, and a Judicial Intern to The Honorable O. Rogeriee Thompson at the United States Court of Appeals for the First Circuit in Boston, Massachusetts.

Bailey received a B.S. from the University of Vermont and a J.D. from Boston University Law School.

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