Experience You Can Trust.
Service You Can Count On.
For over 15 years, we’ve helped property owners maximize returns, minimize stress, and confidently navigate every aspect of rental ownership.
Our Story
At Property Management of Southern Maryland, our journey began the same way many of our clients’ journeys do—with real estate investments and a desire to protect them. What started as managing our own properties quickly grew into a passion for helping other property owners achieve success while avoiding the stress and uncertainty that often comes with rental ownership.
Today, we are proud to be one of Southern Maryland’s most trusted property management companies, serving property owners, investors, and tenants throughout Charles, Calvert, and St. Mary’s Counties.
With more than 15 years of hands-on experience, we’ve built our reputation on honest communication, dependable service, and a commitment to doing things the right way. We understand that every property represents more than just an investment—it represents hard work, financial goals, and a vision for the future. That’s why we approach every property as if it were our own.
Whether you own a single rental home or a growing portfolio, our team is here to provide the expertise, support, and peace of mind you deserve.
15
Years of Experience
131
Satisfied clients around Southern Maryland
245
Current Rental Properties
The Goal
Our Mission
OUR OBJECTIVE IS SIMPLE:
To protect and maximize our clients’ investments while providing exceptional service to both property owners and tenants.
We believe successful property management is built on strong relationships, clear communication, proactive maintenance, and a genuine commitment to helping everyone involved succeed.
The Outlook
Our Vision
We envision a future where Property Management of Southern Maryland continues to set the standard for professional property management throughout the region.
As we grow, our commitment remains the same: creating greater opportunities for our clients, protecting property values, and delivering exceptional service to both owners and tenants.
By continuously improving our services, investing in our team, and maintaining the personalized approach that defines our company, we strive to help owners achieve their investment goals, provide residents with places they are proud to call home, and earn the trust of the communities we serve.
The Property Management of SOMD Team
The Faces Behind Your Success
Chris Gadway
Co-Owner
A proud U.S. Coast Guard Veteran, Chris brings more than 15 years of property management and real estate experience to the company. His vision for Property Management of Southern Maryland was built around helping property owners achieve long-term success while delivering exceptional service and accountability.
Julie Gadway
Co-Owner
Julie oversees the financial operations of the company, including accounting, owner reporting, and tax documentation. Her attention to detail and commitment to accuracy help ensure our clients have confidence in every aspect of their investment’s financial performance.
Lola Gilbert
Regional Manager - St. Mary's County
With nearly two decades of experience managing rental properties throughout Southern Maryland, Lola brings invaluable industry knowledge and leadership to our team. Her expertise helps ensure smooth operations for both owners and tenants alike.
Bri Tomlinson
Office Administrator
Bri manages day-to-day operations, communications, marketing initiatives, and administrative processes. Her focus on organization, efficiency, and client experience helps keep everything running smoothly behind the scenes.
James Paulin, Jr.
Property Compliance Representative
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CJ Ward
Home Technician
CJ is our go to trouble shooter. he drives more miles than any other employee, constantly on the move. On weekends when not working (this is property management after-all), CJ can be found on the river or the bay, fishing, crabbing, or just plain floatin’
Tony Wineke
Home Technician
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THE BEST OF THE BEST
We’re honored and humbled to have been named Best Property Management Company in the Best of Southern Maryland awards for four consecutive years — 2022, 2023, 2024, and 2025.
Voted on by local residents across Charles, Calvert, St. Mary’s, and Prince George’s Counties, this recognition reflects our team’s commitment to providing exceptional service to both property owners and tenants.
We’re also proud to partner with Ken Phipps, who was named Best Real Estate Agent in 2023 and 2024 and was a finalist in 2025. His expertise in real estate sales, acquisitions, and leasing provides valuable support for clients looking to grow their investments.
These awards are a reflection of the trust our clients place in us and our continued dedication to serving Southern Maryland with professionalism and care.
4 Consecutive Years. One Commitment: Exceptional Service.
Partner With a Team That Treats Your Property Like Their Own
Owning rental property should be rewarding—not stressful. Whether you’re a first-time landlord or an experienced investor, our team is here to help you protect your investment, maximize returns, and enjoy greater peace of mind.
EXPERIENCE THE AWARD-WINNING SERVICE PROPERTY OWNERS TRUST.