At Flagship Property Management, we see ourselves not just as property managers, but as devoted stewards of Annapolis—a city rich with history and character. Since our founding in 2023, our mission has been clear: to preserve the architectural treasures that define our community while reimagining them into modern, luxurious spaces for today’s residents. Every building we purchase and restore carries a story, and we take pride in honoring that legacy with craftsmanship, care, and vision. From historic storefronts and offices to luxury apartments and the iconic Gibson’s Inn, each property in our portfolio reflects both the timeless heritage of Annapolis and the vibrant future we are helping to shape. By combining attentive property management with a deep respect for history, Flagship creates exceptional places to live, work, and gather—ensuring that the soul of Annapolis not only endures but thrives for generations to come.
At Flagship Property Management, we’re more than a property management company—we’re invested neighbors dedicated to the heart of Annapolis. As a locally owned and operated business, we take pride in strengthening our community by making property ownership effortless, rewarding, and secure. Our experienced team of managers and maintenance professionals treat every building with the same care and attention we would our own, ensuring that every detail is handled with precision. From behind-the-scenes operations to creating welcoming spaces where tenants feel right at home, we believe it’s the personal touches that set us apart.
We also embrace the latest technology to make property management simple and seamless. Tenants enjoy 24/7 access to an intuitive online portal for rent payments, maintenance requests, and updates, while property owners benefit from clear communication, complete transparency, and peace of mind. From marketing and leasing to landscaping, renovations, and day-to-day maintenance, we manage every aspect of your investment. With Flagship, you can relax knowing your property is cared for with integrity, expertise, and a commitment to excellence.
Founded in 2023, Flagship Property Management was built on a vision to honor Annapolis’s rich past while shaping its vibrant future. Our work extends far beyond traditional property management—we serve as caretakers of the city’s most treasured historic landmarks. With thoughtful restoration and modern reinvention, we breathe new life into Annapolis’s iconic architecture, preserving its legacy while creating luxury apartments, offices, storefronts, and community spaces designed for today’s lifestyles.
Our portfolio now includes more than 30 apartment residences, 6 professional offices, 4 unique storefronts, and the celebrated Gibson’s Inn—three historic buildings thoughtfully restored to offer 20 beautifully appointed rooms. Each property embodies the spirit and story of Annapolis while providing comfort, connection, and character to those who live, work, and visit. At Flagship, we believe every building has a soul, and we are proud to preserve that legacy while curating exceptional places where history and modern living thrive together.
