Realtors® in Chesapeake

More than 254,000 people live in Chesapeake. It’s home to many professional athletes and has the most deepwater canals in the nation. According to, the current market is ideal for buyers. Thanks to more supply than demand, the average home price is $360,000 and rising at an annual rate of just 2.9%. Chesapeake is a great place for families and young professionals to relocate because of its high quality of life, top-notch schools, and abundance of employment and business opportunities. Great Bridge, Hickory, and Greenbrier are among the top choices for neighborhoods. The best brokers in the city are here to help you.

Chesapeake Realtors® & Real Estate Agents

Cova Home Realty
Ryan Fleming

Ryan Fleming is passionate about assisting people in achieving their real estate goals in addition to taking great pleasure in providing his clients with exceptional service. He is committed to making sure their needs are met and that they enjoy the process as a whole. Due to his expertise and in-depth understanding of the local market, Ryan is the best option for those looking to find the ideal residence or investment property. Ryan is an enthusiastic volunteer who devotes his time and energy to organizations including Crossroads Church San Antonio, Children’s Emergency Relief International (CERI), and Christus Santa Rosa Hospice in addition to his real estate job.

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NextHome Luxury Boutique
market_expert Queen Claudine Ellis

Queen Claudine Ellis is a highly successful Realtor in Virginia with over 15 years of experience. She has earned numerous accolades, including the Top 100 Award and the Woman of Achievement Award from ACHI Magazine. Claudine holds a bachelor’s degree from Norfolk State University and a master’s from Harvard University. In addition to her career in real estate, she is also a philanthropist, volunteering at the USO and working with the Voice of Revival program. Claudine is in demand as a public speaker and is the author of a book on property investing.

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Rose and Womble Realty
most_responsive David and Kim Wilkey

David and Kim Wilkey are the premier real estate duo in Chesapeake and leaders of the Wilkey Extreme Team, one of the top groups in the area. With their extensive knowledge and wide connections, they know how to seal the deal. If you’re looking to buy, sell, or invest, David and Kim have the skills and experience to make it happen. They’re known for going the extra mile to help their clients achieve their goals. When it comes to getting the job done, Wilkey Extreme is the team to beat.

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Signature Realty Select
most_reachable Janice Hollowell

The real estate markets in Chesapeake, Virginia Beach, Portsmouth, and Norfolk have been dominated by Janice Hollowell since 1989. She is the agent buyers turn to when they want the best deal. Janice, an expert in financing and negotiating techniques, claims that every property she works with is ultimately sold. The best in her field, she has been a success in the business for more than three decades thanks to her undeniable charm and incredible talent. Give Janice a call if you want to turn your house-hunting fantasies into reality.

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Triumph Realty
most_responsive Rosalind Levy

One of the top-producing brokers in the Chesapeake region is Rosalind Levy of Triumph Realty. With years of experience, she is prepared to assist you with the purchase, sale, or investment of property because she has a thorough understanding of the local industry. Rosalind has a reputation for having a keen business sense and for being able to make the transaction process enjoyable. She has also received a significant number of positive reviews from satisfied customers. Rosalind is a specialist in her field and the ideal choice for all of your real estate requirements.

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The Bryant Group Real Estate Professionals
most_responsive Jenn Bryant

As head of The Bryant Group Real Estate Professionals, Jenn Bryant has been assisting the Chesapeake and Hampton Roads markets since 2003. Her degree in business, finance, and marketing from Old Dominion University has perfectly complemented her real estate skills. Jenn is a Certified Residential Specialist, Accredited Buyer’s Representative, Military Relocation Professional, and Certified Distressed Property Expert. She’s earned a fantastic reputation in the community and has connections with some of the best service providers in the area. Jenn started her own organization in order to help more clients achieve their goals.

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Lonnie Bush Real Estate
market_expert Lonnie Bush

Lonnie Bush is a real estate expert and Navy veteran with a passion for helping people buy, sell, and invest in Chesapeake, Hampton Roads, and the surrounding areas. As the founder of Lonnie Bush Real Estate, he has formed a team of award-winning agents who make sure every client gets VIP treatment. An investor himself, Lonnie loves sharing his wisdom with others to help them make smart decisions. When he’s not closing deals, he can be found coaching his kids’ sports games, cycling, or spending time on the golf course.

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Judy Reed Realty
most_reachable Judy Reed

Judy Reed is a successful real estate agent who is in the Top 1% of all brokers nationwide. She has won numerous accolades, including the RE/MAX Diamond Club, Platinum Club, and Lifetime Achievement awards. Judy is also a 5-Star Zillow Agent and has received Circle of Excellence honors for her 40 years of service. She oversees Judy Reed Realty, the top team in the region. They have a great deal of combined experience and an incredibly successful track record. Judy and her group are the professionals to turn to if you’re looking to buy or sell local properties.

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Community Partner Group
best_negotiator Tyson Bradley

Tyson Bradley established Community Partner Group, a full-service real estate team in the Chesapeake and Hampton Roads area. His specialties include investors, first-time homebuyers, luxury listings, and VA military buyers. In less than 10 years, Tyson has advanced to the position of one of the top-producing agents in the region. He has received numerous accolades, including the Hampton Roads Magazine’s 5-Star Award and The Virginia-Pilot’s “Best of the Beach” honors. Tyson is dedicated to continuing his real estate education and using his expertise to help his clients accomplish their goals.

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Trustworthy Agents Group
most_reachable Robert and Nate Pickles

Robert and Nate Pickles founded Trustworthy Agents Group, one of Chesapeake’s top real estate teams. With almost 40 years of experience, they are authorities on the local market. The team’s website is a comprehensive resource for those looking to buy or sell in Virginia Beach, Chesapeake, Suffolk, Norfolk, Portsmouth, Hampton, and Newport News. They offer listings with comprehensive details for new construction, short sales, foreclosures, resale homes, condos, and renovated properties. Trustworthy Agents Group will help you find the most affordable, high-quality homes that meet your needs so that you can live a better life.

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Keller Williams Chesapeake/Western Branch
rising_star Jarrett Caldwell

Jarrett Caldwell embarked on his real estate journey in 2008 as a real estate investor. As a military spouse with more than 20 years of active duty service, Jarrett has acquired properties in various locations. In 2017, he decided to represent buyers and sellers by purchasing residential, commercial, and investment properties. Jarrett’s marketing degree from Tiffin University and expertise in real estate investment provided him with an advantage in his career. He has experience in tailored digital marketing and advertising and remains current with the latest real estate technologies and industry trends. Jarrett specializes in military relocations, first-time home buyers, and the programs that cater to them.

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Berkshire Hathaway HomeServices Towne Realty
Johnathan King

Johnathan King is a highly respected real estate professional known for his impeccable integrity, strong work ethic, and commitment to innovative solutions. Raised in a small farming community, he understands the value of honesty and hard work, qualities that continue to define his career. As a representative for sellers, buyers, investors, and others in the local Tidewater market, John brings a wealth of experience and expertise to each transaction. His exceptional communication and negotiation skills enable him to build lasting relationships with his clients and proactively address any challenges that may arise. Above all, he is dedicated to providing unparalleled service and always places his clients’ interests first.

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RE/MAX Ultra
market_expert Michael Zimmerman

Mike Zimmerman is a seasoned real estate and mortgage professional with a proven track record of success. He has achieved the prestigious RE/MAX Hall of Fame member status and has consistently ranked in the top 1% of agents. In addition, Mike is a RE/MAX Platinum Club Member for 2016-2020 and achieved Chairman Club status in 2021. With a focus on providing exceptional service, he is highly regarded for his expertise in selling, marketing, and negotiating. He approaches each transaction with an unwavering work ethic, energy, and attention to detail. Mike is dedicated to understanding his client’s unique needs, thoroughly educating them, and securing the best deal possible while ensuring a fun and enjoyable experience.

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CoVA Collective Realty, LLC
rising_star Megan Morris

Megan Morris and her colleagues at CoVA Collective Realty are among the top Keller Williams teams in Chesapeake. The agents have their own unique strengths, and their sales keep rising as a result of their combined efforts and dedication. CoVA Collective was recognized as the Top Team at Keller Williams Coastal VA in 2018, while Megan was personally honored as the Top Listing Agent at her office in 2017. If you’re looking to buy or sell property in the Chesapeake area, Megan and her staff should be your first call.

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The Ron Sawyer Team
best_negotiator Ronald Sawyer

The Ron Sawyer Team is a full-service real estate group serving all of Chesapeake, Hampton Roads, and the surrounding areas. They specialize in new construction, short sales, property management, and first-time homebuyers. Founded and led by Ron Sawyer, they are dedicated to giving their clients the best results possible. The organization’s honors are numerous, including being members of the RE/MAX Chairman’s Club Team, Diamond Club Team, and Circle of Legends. In addition, Ron has personally won his firm’s Lifetime Achievement Award and has been inducted into its Hall of Fame.

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