Director, Real Estate

Job Category:
Administration & Management

Milton Hershey School (MHS) is one of the world’s best pre‑K through 12th grade private schools, where approximately 2,200 students from disadvantaged backgrounds are provided with a cost‑free home and a top‑notch education. Thanks to the generosity of Milton and Catherine Hershey in 1909, the school is fully endowed today, with the resources to ensure students can thrive. The school has prepared over 12,000 graduates to lead fulfilling and productive lives and is expanding to serve more students.

MHS is seeking an experienced and mission‑aligned Director of Real Estate to oversee a diverse and expansive portfolio of more than 160 properties across 2,200+ acres. Reporting to the Vice President of Administration, this leader is responsible for the full lifecycle management of all Milton Hershey School Trust Directly Held Real Estate, ensuring that all holdings strategically support MHS’s mission, long‑term vision, and campus master plan.

This role requires a seasoned real estate professional with strong strategic planning capabilities, deep technical expertise, and exceptional leadership skills.

• Strategic Leadership & Planning.
• Lead real estate strategic planning and coordinate the school’s real estate master plan.
• Ensure all real estate holdings align with MHS’s strategic plan and campus master plan.
• Oversee acquisitions, gifts, sales, leasing, easements, and related transactions.
• Maintain accurate and current inventory records for all properties.
• Collaboratively ensure exceptional property maintenance and conduct annual appraisals.
• Oversee annual financial projections, tax record keeping, and compliance.
• Coordinate the capital plan for real estate assets.
• Team Leadership & Stakeholder Engagement.
• Supervise and develop a team of three real estate professionals.
• Build and maintain strong relationships with internal and external stakeholders, including legal, finance, facilities, community partners, and regulatory entities.

• Minimum of 8 years of experience in real estate management.
• Active brokerage license required.
• Certified Property Manager (CPM) and/or Certified Commercial Investment Member (CCIM) credentials are a plus.

• Proficiency with Microsoft Office applications and real estate‑related software.
• Strong understanding of real estate markets, regulations, valuation, and best practices.

• Demonstrated success in innovative problem‑solving and sound decision‑making.
• Exceptional ability to manage multiple complex priorities and projects independently.
• Strong leadership skills, including relationship building, negotiation, and team development.
• High level of professionalism, discretion, and attention to detail.
• Demonstrated integrity and alignment with MHS’s values, serving as a role model for students.
• Eagerness to engage with MHS students as part of the school’s whole‑child approach.

Milton Hershey School does not discriminate against applicants or employees, in hiring, promotion or any terms or conditions of employment, on the basis of race, color, national or ethnic origin, ancestry, sex, age, religion or religious creed, veteran status, disability or use of a guide or support animal because of the blindness, deafness or physical handicap of the user or because the user is a handler or trainer of support or guide animals, or any other status protected under applicable federal or Pennsylvania law.

Milton Hershey School does not discriminate in admissions or other programs and services on the basis of race, color, national or ethnic origin, ancestry, sex, religious creed or disability. Read important MHS policies on equal opportunity and diversity, equal employment opportunity, and more.