Commercial Real Estate Legal Assistant

Winderweedle, Haines, Ward & Woodman, P.A., a long-established and highly regarded Winter Park law firm, is seeking an experienced Commercial Real Estate Legal Assistant to join our transactional team. Our real estate practice handles complex commercial acquisitions, development projects, leasing, and multi-million-dollar financing transactions throughout the country. The work is sophisticated and fast-paced — but our environment is professional, collaborative, and sustainable.

This position is ideal for an experienced legal assistant who values high-level transactional work and client exposure but prefers a collegial setting over large-firm bureaucracy.

You will work directly with experienced real estate attorneys on active commercial matters from start to finish. This is a true transactional role — not purely administrative support.

• Coordinating commercial loan closings and real estate transactions nationwide
• Managing closing checklists, signature packages, and post-closing deliverables
• Preparing, formatting, and revising transactional documents
• Conducting due diligence (public records searches, entity filings, UCC searches, county/state databases)
• Tracking deadlines and maintaining transaction timelines
• Communicating professionally with clients, lenders, title companies, and opposing counsel
• Managing electronic and physical file systems
• Overseeing file intake, conflict checks, and closing procedures
• Providing proactive calendar and workflow support

We value legal assistants who take ownership of their matters, anticipate needs, and operate as an integral part of the transaction team.

• Sophisticated commercial transactions nationwide — without large-firm red tape
• Direct access to attorneys and meaningful involvement in complex deals
• Manageable structure and clear communication
• Professional, respectful workplace culture
• Long-term stability in a well-run firm
• Competitive compensation based on experience
• Generous PTO and eight paid holidays
• Health, dental, vision, disability, and life insurance
• 401(k) with firm contributions
• Free covered parking in Winter Park

We are seeking someone who wants to be part of a strong team and contribute meaningfully to high-quality transactional work — in an environment where professionalism and balance coexist.

Qualified candidates should send resumes (cover letter optional) to  Equal Opportunity Employer.

• Minimum 3 years of law firm experience supporting a commercial real estate or transactional practice
• Experience coordinating commercial loan closings
• Strong understanding of real estate terminology and closing workflows
• Advanced proficiency in Microsoft Word (styles, track changes, document comparison tools)
• Proficiency in Excel and Adobe Acrobat (or similar PDF platforms)
• Experience with document management systems (Perfect Practice a plus)
• Exceptional organization and attention to detail
• Ability to manage multiple transactions simultaneously
• Strong written and verbal communication skills
• Professional, client-service oriented demeanor
• Associate or bachelor’s degree preferred but not required