Chesapeake Property Management Services

Are you looking to hire a property manager in Chesapeake, VA? If you are, then you’ve come to the right place!

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1400 +
Doors Managed
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1400 +
Owners Served
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2500 +
Tenants Served
Chesapeake PM

If you’re looking for a professional to help manage your Chesapeake, VA, rental property, Osprey Property Management is here to help.

Since 1999, we have provided a full and extensive range of management services that gives property owners assurance knowing their rental is in good hands. From performing detailed market analyses, screening tenants thoroughly, and conducting regular inspections, Osprey Property Management has you covered.

We operate with an accountability approach to our services. This means we get paid only if we’re able to find a suitable tenant for your rental property. We call this our “Guaranteed Rent” program. We ensure that your Chesapeake property will have quality tenants in 60 days, or else we pay for you.

Our headquarters are located in Virginia and we’re presently serving the following areas in Hampton Roads:

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What Others Say

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The team at Osprey Property Management is amazing! Such a great company and a group of total professionals. Nicole K has always been a great resource; she is always very knowledgeable, responsive, and professional. I would highly recommend this team to anyone. Thank you, Nicole!

Lauren Cook
Rental Property Owner
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Angela B. manages my property, and does a phenomenal job. I live out of state, so making sure that I can trust my property manager to look after my home as if it were their own is of the utmost importance. If you are looking for peace of mind to manage your property, she is top notch!

Laurie Oldham
Rental Property Owner
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Jade and the Osprey Property Management Team are amazing! They are great to work with, easy to get a hold of, and very knowledgeable! Jade is always available to answer any questions I have! They took the stress out of managing my rental! I would highly recommend it!

DeAnna V
Rental Property Owner
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The team at Osprey property management, led by Ruth Ann, has provided expert service for our rental property for the past 5 years. From promptly finding quality renters, to coordinating repairs and routine maintenance, to providing the entire revenue and cost accounting service that is used to file tax returns, Osprey Property management is superb.

Ronald Babski
Rental Property Owner
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Guaranteed Rent, Every Month—No Hassle, No Risk

Tired of late or missing rent payments? With Osprey Property Management’s Guaranteed Rent Program, you’ll receive on-time rent payments every month, no matter what. Whether your Chesapeake property is occupied or vacant, your income is secure.

  • Consistent Cash Flow
  • No Tenant Payment Delays
  • Stress-Free Property Management

Experience true peace of mind with our reliable rental income solution.

Why Choose Osprey Property Management?

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Guaranteed Rent Program

Never worry about late or missing rent payments again. Our Guaranteed Rent Program ensures you receive on-time rent every month, no matter what.

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24/7 Owner Portal Access

Stay in control with real-time access to financial reports, maintenance updates, and tenant details anytime, anywhere through our secure owner portal.

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Cutting-Edge Technology

We utilize PMOS—an advanced property management operating system—to streamline leasing, maintenance, and tenant communication, ensuring peak efficiency.

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Optimized Rental Income

Our data-driven pricing strategy and market expertise help you maximize rental income, reduce vacancies, and secure the best tenants for your Chesapeake property.

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Proactive Property Maintenance

With routine inspections and preventative maintenance, we catch small issues before they become expensive problems—saving you time and money.

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Superior Tenant Screening

We conduct a thorough vetting process that includes background checks, credit assessments, and rental history verification, ensuring you get reliable, long-term tenants.

Local Market Insights

Expert Property Management in Chesapeake

Two kayakers paddling through the Great Dismal Swamp National Wildlife Refuge

With its natural beauty, cultural landmarks, and growing appeal, Chesapeake is an ideal location for renters seeking both comfort and convenience. From scenic trails to rich heritage sites, the city offers a unique blend of outdoor adventure and historical exploration that enhances its residential charm.

At Osprey Property Management, we help property owners tap into Chesapeake’s rental potential with expert guidance, personalized service, and full regulatory compliance. Whether you’re renting out a single-family home near Chesapeake City Park or a multi-unit property close to the Great Dismal Swamp, our team ensures your investment thrives.

Why Renters Choose Chesapeake?

  • Family-Friendly Atmosphere
    Quiet suburban neighborhoods, spacious parks, and a strong sense of community make it perfect for families.
  • Convenient Location
    Easy access to major highways and proximity to Virginia Beach and Norfolk offer both work and leisure convenience.
  • Great Schools and Education Options
    Highly rated public schools and nearby colleges appeal to families and students alike.

Trust Osprey Property Management to handle every aspect of your Chesapeake rental with precision and expertise.

Meet The Team

RuthAnn Fields

Principal Broker/President

Cat Nicholls

Resident Services

Kathy Flores

Owner Services

Connor Lowery

Maintenance
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Free Resources

Guide to Finding the Best Property Manager in Hampton Roads

Whether you’re a seasoned investor or getting started as a new rental property owner, you’ve probably faced a few challenges that come with operating your properties. 

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Free Resources

How to Grow a Real Estate Portfolio in Virginia Beach

In this guide, we will cover essential topics such as getting started, managing a growing portfolio, investment strategies, out-of-state investing, and more.

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Free Resources

Expert Guide to Rental Property Management

Many first-time rental property owners aren’t sure what it takes to find good tenants, keep up with maintenance, and collect the rent (on time). 

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Speak with Hampton Roads Experts

Prefer a call? Talk directly with property management experts in the Hampton Roads area.