Select Land and Homes Inc. is an independent and locally owned real estate company focusing on personalized individual service. Our competent and sensitive approach continues to produce positive and lucrative results for our customers.





Tel: 410-708-0956

Billy, the Broker of Select Land and Homes, is an Eastern Shore native with over 34 years of full time, local real estate sales and management experience. Billy specializes in the sale and management of Farm, Residential, Waterfront, and Commercial properties in Kent, Queen Anne, and Lower Cecil Counties.

Billy has consistently produced over ten million dollars worth of sales volume per year for the past fifteen years and three times in the past eight years has been awarded the leading sales producer for the Bay Area Association of Realtors. Billy earned his GRI (graduate of the Real Estate Institute) and Broker designations in 2000.

Billy enjoys coaching youth sports, hunting, fishing and working on his farm with is wife, Nan and children Miles and Hayley.





Tel: 410-708-5423

Miles, Sales Associate of Select Land and Homes, was born and raised in Chestertown. Miles is familiar with the real estate business as his father and grandfather both were Brokers. He has a deep interest in all types of properties and enjoys exploring real estate.

Miles graduated from Auburn University with an honors degree in Agriculture Business and Economics. His favorite hobby is studying animals through hunting, fishing and photography. While in college, Miles researched and volunteered at the Auburn Raptor Center, the largest raptor center in the southeast. Miles is a current member of the Chesapeake Bay Foundation, Bay Area Association of Realtors and National Association of Realtors.





Tel: 410-200-1224

Courtney Chipouras is a native of Rock Hall, Maryland. She recently joined Select Land & Homes after over 19 years as a top-producer at a leading global communications and technology company. She was inspired and educated by her mother and great uncle, both Realtors, and inherited their passion for the business. Courtney has developed a keen eye for design after living in older homes, new construction, and recently taking on her own ‘fixer upper.’ Real estate was a natural career course for her. She loves helping clients realize their residential dreams. One glowing testimonial sums up all of Courtney’s attributes, which would make any buyer or seller want her as their partner:


“Courtney is an absolute pleasure. She listens to your needs/wants, inserts local knowledge and expertise when needed, and was reliant through every step of the process of purchasing a home. She is always accessible, as well as prompt and thorough with anything that requires a response or an explanation. I know we were not every Realtor’s dream clients, however Courtney is absolutely a dream to work with. A 110% positive experience!”

Courtney is a graduate of Salisbury University where she played varsity tennis. She holds her MBA in Marketing from Wilmington University. Courtney volunteers as the assistant girl’s tennis coach at Kent Island High School and coaches the HERO Boy’s Run Club at Kennard Elementary School in Centreville. Courtney and her husband reside in Prospect Bay and are members of the Naval Academy Sponsor Program. She also enjoys traveling and fishing as often as possible.

Our office is located in the Heart of Chestertown's Historic District on the corner of High and Queen Streets just one block off the scenic Chester River. The office underwent a complete restoration in the winter of 2002-2003. Our unique display windows on High Street offer our listing customers some of the greatest advertising exposure to the many visitors of Chestertown and Kent County! If you are unable to find a property of interest to you on our web site, please do not hesitate to contact us. We have access to the region's extensive inventory of properties!

The market is changing everyday and with our extensive knowledge of the region we will be happy to keep you informed as new properties come available. We are often able to locate properties for our customers prior to them hitting the market!

Select Land & Homes

127 High Street, Chestertown, MD 21620