“Diane is a wonderful agent. She is very professional, courteous and knowledgeable agent. Recommend her as a excellent agent that goes above and beyond to get the job done.”
Pearson Smith Realty
- Agent Pronto
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- St. Michaels
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 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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St. Michaels real estate Market Report.
Information and statistics on the latest trends in the St. Michaels real estate market. *
Latest Rolling 3-Month Snapshot
Jul 1, 2026 - Sep 30, 2026
Median sale price
$1.5M
+61%
from Q2 '26
Median list price
$787K
-39%
from Q2 '26
Active listings
24
-7.7%
from Q2 '26
Homes sold
9
No change
from Q2 '26
New pendings
10
-17%
from Q2 '26
New listings
11
+10%
from Q2 '26
Quarterly Pricing Trends for St. Michaels
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for St. Michaels
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for St. Michaels
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for St. Michaels
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for St. Michaels
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for St. Michaels
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
24
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).
St. Michaels currently reflects a seller-leaning market, with the local gauge reading in seller’s favor even as conditions moderate. Months of supply has climbed to 4.6 in this rolling three-month view, up sharply from a year ago, indicating buyers have more options than they did last year.
Home values have surged over the past year, with the typical home value up more than 150 percent compared with the same three-month period a year earlier. At the same time, median list prices are down year over year, and the average sale-to-list ratio has edged below 95 percent, suggesting sellers are adjusting expectations while still achieving strong prices.
On the activity side, the number of homes sold over the rolling three months has fallen by nearly a third year over year, and new listings and pending sales are also lower than last year. Homes are taking longer to sell, with median days on market rising to 111 days, while active listings are modestly higher than a year ago, giving buyers a bit more breathing room. Buyers and sellers who want to navigate these shifting dynamics can turn to Agent Pronto to connect with a local agent who understands the St. Michaels market.
Learn more about what St. Michaels has to offer.
St. Michaels offers residents a welcoming waterfront town with preserved history, vibrant local shops and dining, boating and outdoor recreation, and a close-knit community that makes everyday life enjoyable.
St. Michaels is a historic waterfront town on the Miles River, known for its walkable streets, maritime heritage, and easy access to outdoor recreation. Residents enjoy a small-town feel with enough modern comforts to support full-time living as well as weekend getaways.
Daily life here centers on the harbor and downtown. The Chesapeake Bay Maritime Museum anchors the waterfront, while the town’s public marina and nearby St. Michaels Harbour Inn Marina & Spa make boating and sailing highly accessible. Talbot Street offers casual and upscale dining, from dockside seafood to coffee and breakfast spots, all within a compact, pedestrian-friendly core.
Families and active residents value parks and open space like Muskrat Park and the St. Michaels Nature Trail. Local schools such as St. Michaels Middle High School and St. Michaels Elementary School serve the community, while larger services and shopping in Easton and Oxford are within an easy drive. Nearby Tilghman Island and Cambridge expand options for dining, events, and employment.
Whether you are relocating, purchasing a second home, or preparing to sell, navigating waterfront regulations, historic properties, and seasonal demand can be complex. A local Agent Pronto recommended real estate agent can interpret neighborhood nuances, pricing trends, and buyer expectations so your move in or out of St. Michaels is more straightforward and less stressful for both buyers and sellers.
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“James did a wonderful job helping us to sell our home in difficult market. HIs negotiation skills are fantastic along with his demeanor. He was able to get us a deal that we were comfortable with. He has a good eye and provided great recommendations on things to address prior to pictures. Overall, I would highly recommend James to sell you home.”
Northrop Realty
“Karen was Great in every way, i am not to good with words i just would like to say, If i would buy another house i would go with Karen again 100%. Karen is professional, a great listener, We bought the house we wanted at the price we wanted .Thank you Karen again for all that you did for us.”
IN-VISION REALTY
“Working with Jamie has been such an amazing experience! She is super attentive to what we wanted in a home and was wonderful at communication with her timely responses to our questions throughout the process! We found our very first home with her and are so excited to move in! My husband and I would most assuredly recommend her to anyone who wants the best in this field!”
Keller Williams Flagship
“We have moved and purchased several homes in the past 3 years. For our home in Delaware, we were very luck to find Dale. As we all know, the stress of finding a home and then moving can be overwhelming. This is where the professionalism, knowledge, and practical experiences of Dale took over. If he didn't have an answer (very rare) he would research and present the best solution. Without a doubt, Dale is the best Real Estate Partner that we have ever worked with in our home search. You and your Family will benefit working with Dale.”
Bayside Realty
“We had an exceptional experience working with Laura Anderson during a very difficult time for our family. After losing our father, we needed to sell our mom’s home in Maryland while living in Virginia, and Laura was truly a lifesaver. We first connected with her about six months before listing, and she immediately provided clear, practical advice on how to prepare the home for sale. She went above and beyond by coordinating with vendors on our behalf, which saved us countless trips back and forth. Laura was responsive, compassionate, and always had our family’s best interests in mind. Thanks to her expertise, she was able to secure a great outcome for our mom. We’re incredibly grateful for her support and highly recommend Laura to anyone looking for a knowledgeable, trustworthy realtor.”
Coldwell Banker Realty
“We couldn’t be more grateful for the incredible experience we had with Amy during the purchase of our first home. From day one, she was patient, knowledgeable, and truly invested in helping us find the perfect place. She guided us through every step of the process with clear communication and genuine care, making what could have been a stressful experience feel exciting and manageable. Highly recommend to anyone looking for a smooth, supportive home-buying journey.”
Chesapeake Real Estate Associates, LLC
“If you call anyone besides Dallas Watson you're wrong. Point blank. Made buying my first home such a stress free, comfortable experience. Top notch knowledge. Top notch professionalism, and communication with Dallas makes you think you're talking to a friend you've known your whole life. On a scale of 1-10 on every category I'd give him infinity! Thank you Dallas! I love the house and loved working with you man! Keep being #1!!!”
Keller Williams Walt Taraila
“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.”
REAL Brokerage LLC
“I have worked with Chevelle on four separate occasions. There is no one better. She is knowledgeable, responsive and an expert negotiator. I have used her on both the seller and buyer’s side and she was a superstar in dealing with both. I have recommended her to family, friends and co-workers and all have been thrilled!”
Monument Sotheby's International Realty
“Lauren was extremely helpful and knowledgeable. She always answered all my questions with a lot of detail, which was really helpful for a first time home buyer. Lauren was super patient with me as we looked at houses all over the place and I was super indecisive.”
Keller Williams Flagship of Maryland
“Debbie is wonderful at what she does! She has years of experience and expertise, gives honest advice and looks out for her clients best interest! She is very responsive and flexible. She sold me my first home ten years ago and I just worked with her again to purchase my new home. 100% recommend her!”
SAMSON PROPERTIES
“Marc helped my partner and I buy our first home. We were new to the whole process and Marc offered much appreciated advice and support every step of the way. When the seller couldn't make our original closing date and we had already gave notice to our apartment building, Marc went above and beyond to make sure we were taken care of. Marc was always one step ahead of us, making sure everything happened as smoothly and fairly as possible. Marc was a true advocate for us and I highly recommend him to all of my friends!”
Washington Fine Properties, LLC
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 covering the housing market in and around St. Michaels. 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. Find your St. Michaels Realtor® or real estate agent today.
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