Three Robust Divisions, One Successful Formula.

Featuring three individual divisions operating in unison under the Chesapeake Investment Group umbrella, we allow investors to benefit from our end-to-end approach. Simplifying the process and maximizing future outcomes: Welcome to the world of Chesapeake Investment Group.



The in-depth experience in local property markets gives Chesapeake Investment Group a strong edge; one that very few are able to proclaim. We maintain strong relationships with bankers, brokers, auction agencies, and market insiders who let us know where to the best opportunities are waiting. Chesapeake Investor Group makes it easy to invest by offering affordable buy-in opportunities and full real estate acquisition, renovation, and rental management services.

We will match a property investment with an individual investor based on their needs

Using investor capital, we will direct the entire sale – from contract to closing.

Whether it’s a resale or a rental, we will rehabilitate the property to obtain the best possible return.

We protect property values by providing expert in-house real estate management services – including upkeep, collections, tenant retention, and more.



Our team of designers and licensed contractors provide a broad range of critical services. From designing and engineering, to construction coordination from inception through project completion, Chesapeake Investment Group takes pride in the execution of each investment property’s construction project. Doing the job right; maintaining project safety; refusing to cut corners – these are all longtime hallmarks of the contracting team at Chesapeake Investment Group

We are involved in every phase of the contracting process. From selecting materials to obtaining permits to executing the actual construction phase, we’ll get it done right.

Time is money. Our team places an emphasis on speed to keep downtime to a minimum and productivity to a maximum, so projects get completed faster.

Budget planning is something we place a prime focus on. We’ll crunch the numbers to accurately calculate total projects costs and ensure investors walk away with a sizeable profit.

By having a comprehensive understanding of local zoning laws and building codes, we know how to avoid potential issues, allowing projects to get finished on-time and on-budget.



The core business of Chesapeake Investment Group is supported by a business infrastructure that includes a traditional property management group to oversee and maintain real estate investments. We currently provide management services to our numerous residential properties including standard servicing of inquiries, collection of all fees and rents and investor reporting/record retention, along with professional facility maintenance, repairs and improvements, for improved cycle times.

Quality properties command quality asking prices. Our management team works hard to ensure that every investment has the highest possible potential for maximum rental rates and value.

One call to us does it all. Whether it’s placing a new tenant or collecting the rent or getting an electrical problem repaired, dealing with it is our business – the only thing investors do is keep an eye on their rising dividends.

We don’t just do the fixing – we prevent the need for costly repairs. Preventative maintenance and periodic routine inspections are held to keep properties in tip-top shape all year long.

Monthly reports clearly detail the profits and losses involved for each property – so keeping tabs on investment expenditures and returns are easier than ever