Rental Property
Management in
Wicomico County

Voted Best Property Management Company on the Eastern Shore!
70+ Reviews
Happy Owners
0 +
Years of Combined Experience
0 +
Total Managed Units
0 +

About Whitehead Rental Management

For property owners, managing rental properties can cost you a lot of time, money and headaches. Let Whitehead Rental Management, Inc. protect your investment, maximize your income, and minimize your stress —all without inconveniencing your daily life. Whether you own a single home or many investment properties, you can depend on the Whitehead Rental Management’s team for attentive, professional property management. We’ll manage even the smallest detail so you can spend your time doing the things that are important to you.

Our Services

We provide professional service and build trust through integrity and reliability.

Property Marketing

Inspections

Maintenance

Rent Collection

Tenant Screening

Brokerage Services

70+ Reviews

What Our Clients Say About Us

Posted on Google Google
Tracie profile picture
Tracie
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
It’s a good rental property I have been here for 9 years wonderful staff any problems I have with my unit they make sure it’s taken care of right away they have really reasonable rent rates and clean nice properties if u are looking for your first place or another location definitely look into whitehead rentals
Posted on Google Google
Whitney Tawes profile picture
Whitney Tawes
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
I’ve had an excellent experience renting from Whitehead Rental Management. From day one, they’ve been professional, responsive, and genuinely attentive to tenant needs. Communication is always clear and respectful, which makes a huge difference when it comes to renting. Any maintenance requests are handled quickly and efficiently, and it’s obvious they take pride in keeping the property in great condition. The home is well-maintained, safe, and comfortable, and I’ve always felt like my concerns are taken seriously. What really stands out is how reliable and fair they are. Everything—from rent expectations to lease terms—is straightforward and transparent, which builds a lot of trust. It’s not always easy to find a landlord who balances professionalism with genuine care, but they absolutely do. I would highly recommend renting from them to anyone looking for a stress-free and positive living experience.
Posted on Google Google
Ammar Alhaddad profile picture
Ammar Alhaddad
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
I’ve been with Whitehead Real Estate Management since 2022 and couldn’t be more satisfied with their service. They handle everything seamlessly, allowing me to be completely hands-off as a property owner. Their ability to find the right tenants is exceptional — my current tenant has been in the property for over three years with zero issues. If you’re looking for a reliable, professional property management company, I highly recommend Whitehead.
Posted on Google Google
Tyrone profile picture
Tyrone
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
Man, what can I say about this business!!!!!!! I’ll start here. Everything about them is phenomenal. I was a tenant at one point and any need that I had…… It was taken care of the most timely manner ever, communication great, and you can tell that it’s a lot of love and care in the business. They always treat you like family. Love, respect, integrity flows through everyone there. Our business relationship is top notch they trust me and I appreciate every opportunity given to me. I wouldn’t trade them for anything. Contact them for all rental and home needs.
Posted on Google Google
Graham King profile picture
Graham King
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
Whitehead Rental Management are the best on the shore, and probably beyond. For the four years and counting that I've partnered with them, they've batted a thousand for responsiveness, proactive management, communication, cost savings, and any special requests I've thrown their way. Always on their A game for me 4 yrs and counting, and at this point I couldn't imagine using anyone else!
Posted on Google Google
Phillip Ellis profile picture
Phillip Ellis
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
Austin is very professional and a great communicator. I look forward to working with him moving forward.

What Sets Us Apart

We Actually Know Your Name

Communication between property owners, tenants & vendors is essential for any rental property management company. Our services are personalized through a commitment to understanding the unique needs and preferences of each client.

We are Experienced Pros

We know communication and maintenance are the two biggest complaints from investment property owners regarding their management company. We are 100% dedicated to answering all of your questions.

Our Systems and Processes

Rental systems, maintenance systems, and eviction systems are vital. Our systems are tried and true, ensuring you have a worry-free experience with Whitehead Rental Management. Our goal is to give you time, money, and freedom to grow your investment portfolio!

Get a Free Rental Analysis

  • Determine what’s the optimal rate for your rental.
  • Discover how we can boost your profitability.
  • See if your property is a good fit for our services.

Get a Free Rental Analysis

Learn what your property should rent out for
More details how we can maximize your profitability
See if your property is a good fit for our services
The free rental property analysis is provided as an informational service to help property owners understand potential rental values and strategies for maximizing profitability. It is based on current market data and expert insights but does not guarantee specific outcomes. The analysis includes an estimated rental rate, suggestions for improving profitability, and an assessment of whether your property aligns with our property management and leasing services. Actual results may vary based on market conditions, property details, and other factors. This service is non-binding and does not establish a contractual relationship.