Roland Labana

​Roland has over 20 years experience in real estate investing and property management.  He has respectfully and loyally represented many clients in purchasing & selling homes and investment properties and consistently exceeds expectations in serving his clients.  Earning his Bachelor’s degree from the University of Michigan in engineering and his MBA from Kellogg specializing in marketing, Roland possesses extensive business knowledge as well as unique expertise in the area of property management, having served as the president of Illuminating Software, a company producing property management software.

We're always looking to expand our pool of talent. We want passionate, dedicated, affable people who love working with our clients to make their home-owning dreams a reality. Making that deep connection with your clients is something few jobs can offer.


For your expertise, we offer:


  • Competitive compensation
  • Generous benefits
  • The prestige of working at one of the metro and suburban areas fastest-growing agencies.
  • Tutelage from experienced agents

HighStreet Realty & Investments is also a dynamic workplace when you're not showing our numerous clients gorgeous properties. We urge you to come check us out – you'll be surprised by how un-like other offices we really are.


You'll also get to meet (and hopefully work alongside) our mascot Ruby, the most adorable French bulldog you've ever met, who has neither bark nor bite.

Jack and Thom officially start HighStreet Realty & Investments, opening an office in Sunnydale (which, they might add, was a great value and a beautiful property – thanks to a keen eye and lots of patience).


who we are

Kevin Matti

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The present day – Jack and Thom are still out there selling houses and making dreams come true.

job opportunities

executives and brokers


Jack hires Thomas Moyer as his first real estate agent, taking on an even larger area of the valley under his purview. Lots of great successes and happiness follow.


Jack and Thom expand even further from the metro area into the 'burbs. They find great success in exploring new markets and new possibilities.


Six new agents get onboarded, as well.

Lisa Berkshire

Lisa, a full time agent and active member of the Bloomingdale and Roselle community, is a graduate of DePaul university and began her real estate career with a strong background in math, finance, insurance and business communications.  She represents both buyers and sellers with commitment and dedication.  Lisa has been professionally trained to satisfy all your real estate needs and keeps current on the latest real estate news, events and topics.  Lisa is also an experienced property manager covering single family and multi-unit properties.

our historY

Jack Pointsman, our founder and CEO, sells his first home to his sister, Amanda, sparking a passion for finding the right house for the right person.

At HighStreet, we specialize in making our clients our #1 priority!  We have  extremely flexible schedules and are available to serve you full-time, including evenings and weekends.   We have experience in both real estate brokerage and investment and serve customers in both the suburban and Chicagoland areas.       

We are…

• Committed to serving a limited number of customers in
  order provide highly personalized service

· Focused on meeting our clients’ individual needs

· Dedicated to making availability and responsiveness the priority with our clients

· Members of the National Association of Realtors and a licensed HUD brokerage


William Randall

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