Hillside Investments

About Us

Hillside Investments, forged from the successors of Dembs Roth and the Osprey Companies, is a full-service real estate company that specializes in acquiring, developing, and managing strong investments.

Our Mission

It is our mission at Hillside Investments to provide our clients with risk-adjusted returns that exceeds expectations while maintaining transparency and accountability.

Throughout our history, we have acquired more than one billion dollars worth of commercial real estate assets across sixteen states with a total footprint that exceeds twenty million square feet. With extensive internal resources and a commitment to excellence, Hillside has an unparalleled ability to capitalize on investment opportunities.

Complete transparency, dedication, and professionalism in our investments are guaranteed to maximize our investors’ real estate experiences.

Strategic Principles

Investment beyond


The Hillside Investments team represents three generations of professional experience in commercial real estate. Our company’s cohesiveness, backed by our cumulative years of experience and knowledge, provides us with the necessary disciplines for integration resulting in unmarked success.

Client Service

We understand that every project and investment is different and as a result, we will tailor our service, process, and procedure to every client in a completely customized fashion. We have the ability to flex and adapt to work creatively with our clients to achieve positive and mutually beneficial results for all parties involved in every transaction.


Hillside Investments has access to and can provide a wide array of financing options for all your investments. The Hillside Investments leadership team has extensive relationships with local, national, and international financial institutions that can craft the most efficient and effective financing options for all deals.

Structural Integration

Hillside Investment’s seasoned professionals understand and act as first-tier service providers offering the highest quality occupancy services and environments. Our ability to provide this level of service starts from the integration of various knowledge bases internal to Hillside; design, budgeting, construction, asset management, financing, etc.

Market Perspective

Hillside Investment’s perspective is complemented by deep, local knowledge that influences economies of scale, best practices and best-in-class people to source, analyze and then embrace investment opportunities, across a vast geographical range.

Tax Strategies

We create tax sheltered returns while realizing our assets' maximum valuation before ultimate disposition. Prior to disposition, Hillside Investment’s seasoned professionals and group of tight-knit consultants can assist in providing our clients with the highest level of tax strategy and planning to maximize and utilize all available tax and financial incentives.


Interested in joining
our team?

Contact us today for more information on available positions and careers with Hillside Investments.

Contact Us