Chesapeake Property Management
Welcome to ProActive Real Estate Services, your premier choice for property management in Chesapeake and the greater Hampton Roads area.
Hiring a Property Manager?
Why Choose Us
Chesapeake Property Management
Managing and maintaining a property as a real estate investment takes a team. Whether you are a first time rental owner or experienced real estate investor, at ProActive Real Estate Services, you will have just that: a team of expert rental managers, leasing agents, maintenance technicians, and property accountants ready to serve you. As real estate professionals, we are always looking forward to new opportunities to help clients reach their goals.
From Day 1, our goal is to set a foundation for success. It starts by having a conversation about you, your property, and where you want to take your real estate portfolio. From there, we will ensure your property is ready for the rental market. We will take care of safety and compliance issues, schedule professional marketing photos, and begin screening rental leads and applications. Once you have a strong tenant in place, our team will provide comprehensive ongoing service from rent collection and maintenance to lease management and property accounting.
Once you are part of the ProActive Real Estate Services community, we will work hard to provide you with complete peace of mind. We pride ourselves on being high-touch communicators and hands-on managers. Our ultimate goal is to keep growing together and to better the Hampton Roads community, one home at a time.
How It Works
Chesapeake Property Management
Managing a rental property in Chesapeake doesn’t have to be complicated. At ProActive, we simplify the process by taking care of everything from start to finish. It all begins with a free rental evaluation, where we assess your property and provide expert guidance on pricing based on current market trends in Chesapeake and the surrounding Hampton Roads area.
Once you're ready to move forward, we professionally market your property to attract quality tenants. Our listings are placed across top rental platforms and include high-quality photography and local targeting to ensure maximum visibility. We handle all tenant inquiries, showings, and applications, giving you access to a wide pool of prospective renters.
Every applicant goes through a rigorous screening process that includes credit, background, income, and rental history checks. Once a qualified tenant is selected, we take care of the lease, deposit collection, and move-in coordination. From that point on, our team manages rent collection, routine maintenance, tenant communication, and financial reporting so you don’t have to.
With ProActive, you stay informed without being overwhelmed. Our owner portal gives you access to real-time updates, monthly statements, and performance reports. We provide hands-on service, proactive communication, and full transparency every step of the way.
Why Chesapeake Property Owners
Choose Us
“We had a very smooth house sale with Gary Layne at ProActive. Knowledgeable, friendly, and took care of the details. Highly recommend!”
Brett Siegfried
“The Property Management has been very helpful through the process of being a tenant. They have been very patient plus polite. Staying at this property was no issue and even if I may have an issue, they'll be there to help solve that issue.”
Jorge "Too Sharp" theboxer
“Gary Layne was our agent and he was extremely helpful and knowledgable! He helped us find the perfect spot for our situation.”
Paul Mahoney
“Gary Layne was remarkably helpful in selling our commercial property. He is very knowledgeable and experienced real estate agent, highly recommended..”
Cecilia Welch
“Gary and his team always go above and beyond for their clients making the home buying or selling process simple and easy. A pleasure to work with!”
Melissa Pierce
“I had a fantastic experience with ProActive. They are total experts in property management (also have great merch).”
Alex Zajdel
“ProActive Real Estate Services help management and sell the townhome , very responsible and trusty”
gracemei65
“Great experience with this group so far. Attention to issues and immediate responses.”
M Huey
“Thank you to Gary and team for fixing problems and being attentive landlords.”
Cory Steiger
“Very professional. He goes above and beyond my expectation.”
Lucimar Musch
“Amazing people!!!”
Javier Santos
“We had a very smooth house sale with Gary Layne at ProActive. Knowledgeable, friendly, and took care of the details. Highly recommend!”
Brett Siegfried
“The Property Management has been very helpful through the process of being a tenant. They have been very patient plus polite. Staying at this property was no issue and even if I may have an issue, they'll be there to help solve that issue.”
Jorge "Too Sharp" theboxer
“Gary Layne was our agent and he was extremely helpful and knowledgable! He helped us find the perfect spot for our situation.”
Paul Mahoney
“Gary Layne was remarkably helpful in selling our commercial property. He is very knowledgeable and experienced real estate agent, highly recommended..”
Cecilia Welch
“Gary and his team always go above and beyond for their clients making the home buying or selling process simple and easy. A pleasure to work with!”
Melissa Pierce
“I had a fantastic experience with ProActive. They are total experts in property management (also have great merch).”
Alex Zajdel
“ProActive Real Estate Services help management and sell the townhome , very responsible and trusty”
gracemei65
“Great experience with this group so far. Attention to issues and immediate responses.”
M Huey
“Thank you to Gary and team for fixing problems and being attentive landlords.”
Cory Steiger
“Very professional. He goes above and beyond my expectation.”
Lucimar Musch
“Amazing people!!!”
Javier Santos
“We had a very smooth house sale with Gary Layne at ProActive. Knowledgeable, friendly, and took care of the details. Highly recommend!”
Brett Siegfried
“The Property Management has been very helpful through the process of being a tenant. They have been very patient plus polite. Staying at this property was no issue and even if I may have an issue, they'll be there to help solve that issue.”
Jorge "Too Sharp" theboxer
“Gary Layne was our agent and he was extremely helpful and knowledgable! He helped us find the perfect spot for our situation.”
Paul Mahoney
“Gary Layne was remarkably helpful in selling our commercial property. He is very knowledgeable and experienced real estate agent, highly recommended..”
Cecilia Welch
“Gary and his team always go above and beyond for their clients making the home buying or selling process simple and easy. A pleasure to work with!”
Melissa Pierce
“I had a fantastic experience with ProActive. They are total experts in property management (also have great merch).”
Alex Zajdel
“ProActive Real Estate Services help management and sell the townhome , very responsible and trusty”
gracemei65
“Great experience with this group so far. Attention to issues and immediate responses.”
M Huey
“Thank you to Gary and team for fixing problems and being attentive landlords.”
Cory Steiger
“Very professional. He goes above and beyond my expectation.”
Lucimar Musch
“Amazing people!!!”
Javier Santos
“We had a very smooth house sale with Gary Layne at ProActive. Knowledgeable, friendly, and took care of the details. Highly recommend!”
Brett Siegfried
“The Property Management has been very helpful through the process of being a tenant. They have been very patient plus polite. Staying at this property was no issue and even if I may have an issue, they'll be there to help solve that issue.”
Jorge "Too Sharp" theboxer
“Gary Layne was our agent and he was extremely helpful and knowledgable! He helped us find the perfect spot for our situation.”
Paul Mahoney
“Gary Layne was remarkably helpful in selling our commercial property. He is very knowledgeable and experienced real estate agent, highly recommended..”
Cecilia Welch
“Gary and his team always go above and beyond for their clients making the home buying or selling process simple and easy. A pleasure to work with!”
Melissa Pierce
“I had a fantastic experience with ProActive. They are total experts in property management (also have great merch).”
Alex Zajdel
“ProActive Real Estate Services help management and sell the townhome , very responsible and trusty”
gracemei65
“Great experience with this group so far. Attention to issues and immediate responses.”
M Huey
“Thank you to Gary and team for fixing problems and being attentive landlords.”
Cory Steiger
“Very professional. He goes above and beyond my expectation.”
Lucimar Musch
“Amazing people!!!”
Javier Santos
Are You Rent Ready?
Find Out Now
Before listing your Chesapeake rental property, it’s important to make sure it’s fully prepared for showings and move-in. Our Rent Ready Checklist helps property owners cover every detail, from cleaning and repairs to safety requirements and curb appeal. A well-prepared home rents faster, attracts better tenants, and reduces potential issues down the line.
