We analyze thousands of real estate agents in Chesterfield and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 2026.*
*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.
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Information and statistics on the latest trends in the Chesterfield real estate market. *
Jul 1, 2026 - Sep 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).
Year over year, Chesterfield’s rolling three-month data shows values holding fairly steady while listing prices climb. The typical home value is down less than 1% from last year, but the median list price has jumped about 15%, suggesting sellers are testing higher price points. At the same time, active listings are up more than two thirds from a year ago, giving buyers more options than they had before.
Looking at recent activity, the latest rolling period through September 2026 shows 10 homes sold and 10 pending sales, both up strongly compared with last year. New listings have risen about 16% year over year, yet months of supply sits at just 1.6 months, reinforcing Chesterfield’s status as a seller’s market. Median days on market have increased to 36 days from much faster conditions last year, indicating homes are still moving but buyers may have a bit more time to decide.
Pricing dynamics have shifted, with only 10% of recent sales closing above list price and the average sale-to-list ratio at about 96%, both lower than a year ago. This pattern points to buyers gaining a bit more negotiating power even as inventory stays tight. With these mixed signals of higher asking prices, modest value changes, and evolving buyer leverage, both buyers and sellers can benefit from Agent Pronto’s help in finding a Chesterfield agent who understands the current numbers and trends.
Chesterfield offers residents a welcoming, connected community with accessible parks, local amenities, and practical services that together support a high quality of life.
Chesterfield stands apart from nearby Anderson and Daleville with its quieter pace and small-town identity that still connects easily to major routes and jobs. Many residents appreciate how quickly they can reach larger employers and shopping along I‑69, then return home to a community where neighbors recognize one another at local events and ballfields.
Life here often centers on local parks and schools. Families make frequent use of Millcreek Civic Center for sports leagues, classes, and gatherings, while outdoor enthusiasts enjoy river access points along the nearby White River and trail connections into Mounds State Park, known for its ancient earthworks and wooded hiking paths. The Anderson Public Library and its outreach services are popular with Chesterfield residents, adding cultural programs and study resources without a long drive.
Everyday needs are close at hand, with local diners, convenience shopping, and quick access to larger retail in Madison County. School options, including those within the Anderson Community Schools, help anchor long term residents and attract new households who value a manageable commute paired with community roots.
For buyers and sellers in Chesterfield, timing and preparation matter in a market where well kept homes can move quickly. Agent Pronto can connect you with a real estate professional who understands local trends, pricing, and how to position your move so you are ready when the right opportunity appears.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“I was a work relocation, and Valerie was simply outstanding in helping me understand the local communities. She has amazing attention to detail and made sure I was informed every step of the way. Great negotiation skills and great tenacity. I've bought and sold several homes, and Valerie was the best agent I have worked with.”
“Honestly, We were in perfect hands. If you're looking for the one that goes out of there way. Matt is one of those guys. There wasn't a time, he didn't answer a text or call. Did his best to take in consideration what we were looking for. He never took long to get us in to see a house we was interested in. He did his best to answer any questions we may have on the houses. He walked us thru the paper work. He was always there to answer questions on the paper work. All around was great thru the process of buying a house. We definitely would recommend Matt to help you!!!”
“Adam's professionalism is exceptional. He is knowledgeable, attentive to details and goes out of his way to help his clients. His marketing skills and network of resources such as photographers, interior decorator, and cleaning team “gets the job done.” We highly recommend Adam for your real estate needs.”
“Working with Alex was an outstanding experience from start to finish. This is the second rental property I’ve purchased in the last two years, and having an experienced Indianapolis realtor who truly understands investment properties made all the difference. We were able to negotiate $20,000 off the list price, which immediately improved my cash-on-cash return and overall equity position. Even better, the property already had a tenant in place at closing, so I had instant cash flow from day one. The rental income exceeds the 1% rule, which was a major goal for me when evaluating this deal. Alex’s knowledge of the Indianapolis investment market, rental comps, and negotiation strategy gave me a real advantage. If you’re looking for an Indianapolis realtor who understands how to structure strong investment deals and identify properties that actually cash flow, I highly recommend working with him.”
“David always went out of his way to satisfy all my questions and concerns. He also always made sure I was getting the most out of buying and selling and I really appreciated that. We shot for the moon and I got exactly what I was looking for. This was a verily nice transition and he made it very easy.”
“Ashley is Very organized and quick to reply to my questions. She explained every step of the way very clearly. In addition the mission of match properties to customer needs is very complex, and Ashley knows how to do it with alot of patience and sensitivy. I HIGHLY RECOMMEND Ashley!!”
“This is my second time around having Metrie help me buy a house and then sell the house. Both times Metrie was efficient, very professional, helpful, knowledgeable and very easy and fun to work with. He gives you very helpful opinions. He is gentle and patient. I loved working with him. I have recommended him to all my friends and people I know.”
“Justin was most helpful dealing with an uncooperative property manager. He got the property sold quickly. I was very happy with his performance.”
“Brad has been great through the whole house buying experience. He never made us feel like we were disrupting him & we never felt rushed, even with our hundreds of questions. This was our first time buying a home & would highly recommend.”
“Tim is a super realtor! He was very responsive, knowledgeable, and helpful! He was always on time when showing houses, and was very patient, I never felt rushed.”
“Regina helped me with my rental properties by providing advise on rental rates, upkeep costs, choosing renters, rent collection, advise on economical furnishings. Regina was also our realtor for our home. She was with us for all aspects of the building of it, choosing our plot, choosing plans, the selling of our previous home, etc. She was so helpful and made the experience an easy move. I would highly recommend her.”
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 covering the housing market in and around Chesterfield. 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.
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.
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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