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Dynamic Team Bare Is a Family Affair

Cheryl Bare and the Home Pros, a team of four including her two daughters and an assistant in White Plains, Maryland, posted more than $40 million in sales volume last year.

Home Industry News
By Barbara Pronin
December 15, 2025, 4 pm
Reading Time: 4 mins read
Dynamic Team Bare Is a Family Affair

Cheryl Bare, third from left, with her Home Pros team. 

Cheryl Bare held two careers for four years, teaching school by day and selling real estate evenings and weekends under the auspices of her father-in-law’s small Maryland brokerage.

“It was the craziest time in my life, working 24/7” said Bare, who spent 15 years as a teacher and teacher trainee while balancing a home life with a husband and three busy kids and the real estate career for which she was licensed in 1989.

In 1992, convinced that real estate was her priority, the Maryland native joined Century 21 New Millennium in White Plains, Maryland, serving such upscale areas as Annapolis, the Solomon Islands, North Beach, and Chesapeake Beach, where she soon became a top producer.

Today, the award-winning Realtor® is the founder and the driving force behind Cheryl Bare and the Home Pros, a team of four including her two daughters and an assistant, which last year posted more than $40 million in sales volume.

Barbara Pronin: Cheryl, what finally motivated you to leave teaching for a career in real estate?

Cheryl Bare: I have a master’s degree in education, and I enjoyed reaching, but after so many years in a classroom, it was nice to spend more time around adults–and my background in education helps me educate clients, especially in markets like we are seeing today, so they know how to prepare and what to expect during their real estate journey.

BP: When did you decide to team, and what led you to do that?

CB: It was about six years ago, and the motivation was simple; I had more business than I could handle. I hired an assistant, Melinda Sasscer, who is still with us today.

BP: And how did your daughters get involved?

CB: My daughter Jenna Anderkovitch, with 10 years as a military spouse, was a natural choice to become a licensed military relocation specialist, as we are near both Annapolis and a Naval air station. My other daughter, Mallory Bare, has a background in psychology. She is a people person at heart with an outgoing personality and great negotiating skills.

BP: Who manages your social media?

CB: We each handle our own to one extent or another, but we also hired a part-timer not long ago who has been doing a great job with that.

BP: And what is your team communication like? How do you ensure that you are all on the same page?

CB: We are a close-knit family. In fact, my son-in-law is a photographer and videographer who does most of that work for us, so it’s nearly impossible not to talk real estate whenever we’re together, which is often. But we stay organized by having a weekly team meeting, when we are each responsible for reporting to Melinda and the rest of the team. We share updates, print-outs, and clientele, and discuss whatever needs the team’s attention.

BP: I imagine it’s hard to keep business out of your shared family time!

CB: It is, but we usually have grandkids around, so we do try not to talk shop.

BP: What can you tell us about the areas you serve?

CB: I am licensed in Virginia, but most of our business is in the southern area of Maryland’s Western Shore. That’s four counties including historic Prince George’s County. It’s a mix of lovely rural and suburban areas with diverse architecture, great dining, several annual festivals and events and a lot of waterfront recreation.

BP: What would you say is the average sale price?

CB: Average is probably $550,000, though many properties are significantly higher.

BP: What do you think sets Cheryl Bare and the Home Pros apart from the competition? 

CB: We have a great reputation as local experts and experienced professionals in our market. People trust us. More than 90 percent of our business today is repeat and referral business. In many cases, we’ve worked with a whole family – aunts, grandmas, siblings, and cousins, and sometimes a second generation. We never sugarcoat things or set unrealistic goals. But we do deliver on what we promise in any given market, and our clients know that.

BP: In what ways do you give back?

CB: We host two client appreciation events each year, and we support the Special Olympics. Also, I serve on the advisory board of our local hospital.

BP: What motivates you to go to work every day?

CB: I love this business because no two days are alike. Every day, every transaction is different. It takes energy, skill, and a lot of flexibility. People are depending on you. But you get out of it what you put into it, and that is exciting to me.

Cheryl Bare Team Listing

3815 Watson Road
Brandywine, Maryland

6 Bedrooms
5 Baths
4,560 Square Feet
5 Acres

Listing Price: $1,000,000

To see the full listing, click here.

To contact Cheryl Bare, click here.

Tags: Century 21 New MillenniumCheryl BareCheryl Bare and the Home ProsReal Estate TeamsRISMedia Team Tuesday
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Barbara Pronin

Barbara Pronin is a contributing editor to RISMedia.

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