- Agent Pronto
- Maryland
- Chester
Find the perfect real estate agent in Chester, MD
We analyze top real estate agents in Chester and across the country to find you the most proven local agents, for free.
Compare the top real estate agents in Chester
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for June 2025. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
The easiest way to find the best real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Home buyers and sellers love Agent Pronto.
Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.
“I couldn't have had a better, more professional agent than Sam Kim. He was tops in not only carrying out the necessary paperwork, but also lending a hand to get the house into marketable condition. Kudos and ten stars to him.”
“Mac McCord is the best real estate agent on this side of the pond! ”
“Matt Arnold is a superior agent. He helped me sell my home and buy my new home. Matt made the process happen quickly and seamlessly. I would highly recommend Matt to everyone.”
“Agent Pronto was the best! I live on the west coast and my home I was selling was on the east coast. They made it better to be able to trust an agent.”
“Agent Pronto recommended John Collins as a possible realtor. John is very professional and organized. Our condo sold in 3 days. Thank you Agent Pronto for sending us the best of the best.”
“My overall experience was well achieved and your Agent, Don Roberts, made my transition very smooth. Great Don went above and beyond to make sure all my questions were answered. He was always available to help me in any matter concerning my house. What a great person Don was, showing nothing but compassion and was very organized. I will rate Don Roberts as a five-star Realtor. Job well done. ”
“The agent with whom I was matched was perfect. Terrific help, thank you!”
“My agent, Nisha Smithrick, was the ideal agent. We had tried to work with other Baltimore agents over the past year and they were terrible. Nisha was amazing from the get-go. She reached out immediately. She asked questions to understand our specific desires for my son's first home. She presented relevant listing within a day. She made herself available for appointments to fit our schedules. She showed us a great selection of homes. She followed up, gave her honest advice. She then was a great sounding board for creating an offer and negotiating with the seller. She was responsive and proactive through the whole process including to inspections and closing. She answered all our questions thoroughly and quickly. I highly recommend Nisha.”
“Quick response with well reviewed agents.”
“Working with Gary was a great experience. He was was very helpful, knowledgeable, and patient.”
Chester real estate Market Report.
Information and statistics on the latest trends in the Chester real estate market, updated for June 2025. *
The typical home value in Chester is projected to be $542,550 for the month of June. May’s finalized data reported the typical value of a home in the city to be $585,000—down 14.59% over the previous 12 months. For comparison, county-level data pegged home values at $532,660 in Queen Anne's County for the most recent reporting period. That number is expected to float around $523,270 in June.
Chester had 24 new listings and 22 listings that went under contract in May, increasing the area’s total available inventory to 64—up 8.47% from the previous month. Inventory is projected to have further increased in June.
Of those 64 active listings, 35.94% reduced their price in the month of May. The median listing price for homes in Chester fell 3.26% from April to May, bringing the current median listing price to $527,250. Based on projected data for June, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In May 2025, the median time for a listed property to go pending was 44 days, compared to 57 days in May 2024. However, in recent months the median number of days from listed to pending appears to be rising. That trend is predicted to have carried through to this June.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Chester has to offer.
Chester offers residents a charming blend of community warmth, scenic environs, and diverse amenities that create a welcoming and fulfilling place to call home.
Chester invites you to experience waterfront living where spectacular sunsets over the Kent Narrows set the backdrop for daily life. Life here blends tranquility and convenience, with convenient access to nearby Annapolis, unique restaurants, and vibrant marinas. Residents make the most of the Chesapeake Bay by kayaking, fishing, and boating from the lively Kent Island Yacht Club. Nature lovers appreciate easy access to the Cross Island Trail, where walkers and cyclists wind through scenic woodlands and marshes teeming with wildlife.
Families in Chester benefit from the area’s highly regarded Kent Island High School, along with active PTA groups and award-winning extracurriculars. Diverse educational programming continues at Matapeake Elementary School, fostering a strong sense of community and lifelong learning. Shopping for local produce is a favorite weekend tradition at the Chesapeake Heritage & Visitor Center, where local history meets curated artisan markets. Dining options range from fresh catches at the popular Fisherman’s Inn to innovative cuisine along the Narrows.
Chester’s distinctive charm lies in its seamless blend of coastal beauty, recreational opportunities, and close-knit neighborhoods, like those found in Stevensville—all set within bustling Queen Anne’s County. Whether you’re downsizing, upgrading, or newly relocating, Agent Pronto can connect you with the perfect real estate agent to help you navigate Chester’s unique market as you settle into this welcoming community.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
Take the guesswork out of finding an agent.
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Chester to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Data analysis with a human touch.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Chester. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Resources for buyers and sellers.
Tips and market insights to make your Chester real estate journey a success.
Frequently Asked Questions
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There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents.
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