Proudly serving the greater Downtown Annapolis area, Flagship Property Management is a locally owned and operated company specializing in residential and commercial property management. We provide full-service solutions tailored to the unique needs of property owners and tenants alike.
At Flagship, we’re backed by a passionate team of property managers and maintenance professionals committed to creating and maintaining vibrant, well-managed communities. Our hands-on approach and dedication to responsive, detail-oriented service set us apart in the Annapolis market.
We utilize the latest property management technology to ensure seamless communication and efficient operations. Tenants enjoy 24/7 access to a user-friendly portal for rent payments, maintenance requests, and important updates—anytime, anywhere.
For property owners, we provide peace of mind. From marketing and leasing to maintenance, landscaping, and beyond, we take care of every detail—making property ownership simple and stress-free.
At Flagship Property Management, we’re more than just a property management company—we’re your neighbors right here in Annapolis. Locally owned and operated, we take pride in caring for our community and making property ownership stress-free and rewarding.
Our dedicated team of managers and maintenance pros treat every property as if it were our own. Whether it’s keeping things running smoothly behind the scenes or making sure tenants feel right at home, we’re all about the details and the personal touch that make a big difference.
We also use the latest technology to keep things simple and convenient. Tenants get 24/7 access to an easy online portal for rent payments, maintenance requests, and updates, while owners enjoy seamless communication and complete transparency.
From marketing and leasing to maintenance and landscaping, we handle it all. You can sit back, relax, and enjoy the benefits of property ownership—knowing your investment is in good hands.
Flagship Property Management was founded in 2023 with a clear vision: to honor the past while shaping the future of Annapolis. Our mission goes beyond property management—we are caretakers of the city’s most iconic and time-honored buildings. By thoughtfully restoring these architectural treasures, we ensure their stories live on while creating vibrant, welcoming spaces for today’s residents and businesses.
Today, our growing portfolio includes more than 30 apartments, 6 offices, 4 storefronts, and the beloved Gibson’s Inn—three historic buildings offering 20 beautifully appointed rooms. Each property reflects the rich heritage of Annapolis while fostering a sense of community, comfort, and connection.
At Flagship, we believe every building has a story to tell, and we’re proud to preserve that legacy while offering exceptional places to live, work, and gather.
Flagship Properties takes great pride in preserving the charm of Annapolis by thoughtfully restoring historic buildings and giving them new life through careful renovation and preservation. Many of these residences are located above locally owned shops, cafés, and other small businesses that give the city its vibrant character. Flagship deeply values the partnerships formed with these business owners, recognizing that their success helps keep the historic districts thriving and full of life. By maintaining the integrity of these buildings while fostering a supportive environment for local commerce, Flagship is committed to helping both residents and small businesses flourish together as part of Annapolis’s rich heritage.
Annapolis is a city steeped in history, featuring colonial architecture, cobblestone streets, and waterfront charm. Whether you’re looking to live here or establish a commercial space, you’ll be part of a vibrant, picturesque community with marinas, scenic views of the Chesapeake Bay, and a lively downtown atmosphere.
The city boasts a dynamic economy driven by tourism, government, education, and maritime industries. This creates a strong customer base for businesses and abundant opportunities to connect with both residents and visitors throughout the year.
Strategically located between Baltimore and Washington, D.C., Annapolis offers easy access to major metropolitan areas while maintaining its welcoming small-town feel.
Home to the U.S. Naval Academy, Annapolis benefits from a steady flow of students, faculty, staff, and visitors, providing a culturally rich environment for residents and a stable population for businesses.
Residents enjoy an exceptional quality of life, including top-rated schools, boutique shopping, farm-to-table dining, cultural events, and outdoor activities like sailing and boating. For businesses, the city’s high foot traffic and engaged community create a prime environment for growth.
As one of Maryland’s top tourist destinations, Annapolis attracts thousands of visitors annually, making commercial spaces highly desirable for retail, dining, and professional services. The city fosters a supportive, close-knit community, with abundant networking opportunities through local events and partnerships that help both businesses and residents thrive.
