We Are Chesapeake Painting Services (but we do a lot more than painting!)

Having spent 20 years in the area, we have built a range of expertise and provide many services. Generally speaking, we are a painting contractor, but we also have many other skills on our team and thus services we provide for your home improvement needs.

We generally expect people to shop around so we believe it is essential to know who you are hiring and what to consider. We try to be very transparent with our capabilities and our pricing so don’t hesitate to ask any questions. Though we take our job very seriously we also like to enjoy a good, genuine relationship with our customers and our team.

Our Mission

We aim to provide remarkable high quality work with extraordinary customer service. We expect the experience of working with us to be genuinely remarkable. Our business relies on word of mouth and referrals. We could not have survived as long as we have and would not continue to grow if we don’t consistently delight our customers and continue to earn their respect and trust.

Our Vision

We built our reputation as the best painters in Annapolis, Md but, in addition to branching far outside of the area these days, we also provide a full range of home services to serve as a one stop shop for discerning homeowners. No one provides the level of accountability and transparency that we do and we aim to earn more of your trust and your business across all of your contracting and home service needs.

Meet Our Team

We are nothing without our team. We only employ true gentlemen (and gentle-ladies) who work hard, care about their families and take pride in the work they perform each day. We support one another, pitch in where necessary, and do our best to keep smiles on not just our customer’s faces but also our own. We believe the more you know about each of us, the more you can trust in the service we provide and the relationship we value.

James GuthJames Guth, Owner – James was raised in the Annapolis area. He is a Broadneck High School grad (we won’t say when) who has been serving the surrounding region for over 20 years. He loves it here and his reputation allows him to continue growing a very successful business because of the honesty and quality he brings to his customers. James has traveled the world extensively, lived and worked at fish canneries in Alaska, spent 6 years in the US Army, earned two university degrees from Towson, and now spends most of his time focusing on Chesapeake Painting and the growing community of customers we have in the area. Feel free to email James anytime.

Stephen ReillySteve, Owner – Steve is also a local, who grew up in Annapolis, graduated from Broadneck High and Salisbury University. Steve manages all of our marketing efforts and growth planning, from print media to the web, business systems and operations tools. He built this fabulous website and helps to capture the essence of our company, which to him is: “..a totally different kind of painting company, one that serves it’s clients better than any other. We also strive to be unique in our character but quality in our final product.” He lives in the area with his wife and 3 kids. Feel free to email Steve anytime.

Our Field Team

We have many talented, dedicated and hard working employees that bring a broad range of experience and skills to our growing team. We hire more men and women each year, who become an integral part of our team. As our services expand to new areas and demand more skills, we are always looking for the best skilled individuals who want to be part of a growth-oriented team. We are always looking for new team members so please check out our Job Openings if you or someone you know is interested in building their career with us.

Our Subcontracting Family

As a growing business that continues to broaden its range of capabilities, we are constantly partnering with the highest quality, most accountable partners in the industry. We won’t take on projects that our team can’t perform at a high level but we always find a way to get the job done through our extensive network of established contractors who bring a wealth of talent and experience to our team. We continue to manage every project, leaving our customers with a single point of contact and not having to manage multiple contractors. Meanwhile we work with each contractor to keep our price points to the same as if you had hired them directly yourself. This is a win win for you the customer, our team at Chesapeake, and our contractors.

Let’s Get Started!