Stephen DeBaise is a seasoned condominium and homeowners association (HOA) management professional with over five years of direct experience managing community associations throughout Connecticut. As Principal of insight real estate & management and a licensed Real Estate Broker, Stephen specializes exclusively in condominium and HOA management, bringing a finance-driven, compliance-focused approach to community governance and long-term asset protection.
Stephen holds a Bachelor of Science in Finance, cum laude, from St. John’s University, and began his career in commercial real estate finance with Webster Bank’s Commercial Real Estate group. There, he supported underwriting and portfolio management for complex credit facilities, contributing to financial modeling, property cash-flow analysis, lease review, and loan approval materials for transactions totaling more than $50 million in credit exposure. This institutional finance background directly informs his disciplined approach to association budgeting, reserve planning, and capital project oversight.
Prior to entering institutional real estate finance, Stephen founded and operated DeBaise Lawn, a successful landscaping company he grew over seven years to 50 weekly accounts and more than 250 satisfied clients before selling the business. This hands-on operational background gives him a practical understanding of vendor management, scope definition, pricing, and field-level execution – experience that directly benefits condominium associations overseeing landscaping, snow removal, and exterior maintenance contracts.
Since transitioning into full-time condominium and HOA management, Stephen has overseen the collection of more than $10 million in association dues, administered over $1 million in repair and maintenance expenditures, and directed approximately $5.3 million in capital improvement projects on behalf of the communities he serves. His expertise includes reserve funding strategies, capital planning, vendor procurement, fiduciary oversight, risk management, and transparent financial reporting for boards and unit owners.
Stephen is deeply engaged in professional and civic leadership. He currently serves as Treasurer of the Wallingford Housing Authority, the President of the Wallingford Rotary Club for the 2025–2026 fiscal year, and actively serves on multiple committees with the Community Associations Institute of Connecticut (CAI-CT), reflecting a strong commitment to industry best practices and ethical governance.
Known for clarity, responsiveness, and strategic guidance, Stephen positions insight real estate & management as a trusted advisor to condominium boards and HOA communities. His management philosophy emphasizes proactive planning, regulatory compliance, and long-term financial stability—ensuring communities are well governed, financially sound, and positioned for future success.