Built On A Foundation Of Success

Chesapeake Investment Group is a leading real estate investment firm based in Baltimore, MD. For nearly a decade, we’ve successfully generated market-leading returns through accelerated and sustained growth of each investment property it represents.

By identifying, purchasing and developing undervalued investment property markets throughout the Greater Baltimore area, we’ve created a foundation of stability for investors, using proven investment strategies that are based on in-depth knowledge of the Greater Baltimore real estate market.

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

Investor Advantages That Offer More

Chesapeake Investment Group generates investment returns that regularly outperform similar wealth building platforms… and offers a greater opportunity for investors and shareholders alike.

  • Low Risk Less Risk, More Gain

    High Returns Bigger Numbers, Smaller Hassles

  • Chesapeake Investment Group is offering investors the opportunity to purchase properties that will be acquired, renovated and rented out – with the possible potential of receiving Section 8 tenancy.

    Although the depressed housing prices and increasing rental rates have remained consistent, the demand for livable housing in the region offers the opportunity to realize higher returns.

  • The properties will be registered under the investors title vehicle of choice and will be fully owned by purchaser. The property, in essence, provides the purchaser with a full guarantee on the investment.

    By tapping into our in-depth knowledge of the Greater Baltimore real estate market and wide base of industry professionals, we are poised to capture properties quicker – and for less – than other investors.

  • Given the structure of the Baltimore rental market, the risks of this opportunityare deemed as very low. Demand for rental properties is strong and long waiting lists of Section 8 tenants increases the likelihood for rapid occupancy of newly renovated homes.

    Our broad portfolio speaks volumes. To date, Chesapeake Investment Group has acquired and rehabilitated over one hundred properties that are collectively worth well over $26.7 million. By building upon a reputation of success, we are indeed putting our Foundation First.

Get To Know Chesapeake... From The Foundation Up.

The real estate market in Baltimore is booming. The city has a very unique layout; each neighborhood has its own personality, and living options run the full gamut – from quaint apartment units to sprawling homes. Above all, Baltimore offers a dynamic array of employment opportunities, cultural features and famous attractions that make it a popular choice for people of all ages and backgrounds to call home.


    Baltimore ranks 8 out of 100 metropolitan areas for its high concentration of jobs in the science, technology, engineering and math fields. A large percentage of residents work in the governmental sector as well, taking the short daily commute to nearby Washington, DC.


    Baltimore is home to the Hopkins Hospital and Johns Hopkins University. These institutions – in addition to employing thousands of residents – are ranked among the world’s top teaching hospitals and provide world-class healthcare to the Baltimore population.


    Baltimore is home to the Super Bowl XLVII Champions, the Baltimore Ravens. Baltimore and Washington also offer baseball fans two teams: the Orioles and the Washington Nationals. In addition, there are a number of local top college teams to follow and attend games.


    Baltimore is in close proximity to three major airports, including Baltimore-Washington International, which is 15 minutes from the city’s downtown, Ronald Reagan Washington National Airport, and Dulles International Airport.


    Baltimore’s impressive housing market is rising steadily, with home sales and rentals up by over 18% this past year. Featuring numerous styles of housing, Baltimore is proving to be popular with first-time homebuyers, along with renters, looking for well-kept, popular neighborhoods to call home.

Creating A Foundation Of Financial Stability. Literally.

A Clear Map For Future Success