Looking for the Best Realtor to Sell Your Calvert County Home? Start With These Questions
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Three agents, three folders, three different numbers. Here is what to ask so the ninety minutes actually tells you something.
Three agents are going to sit at your kitchen table over the next two weeks. All three will be pleasant. All three will have a folder. At least one will tell you a number that makes your stomach flip in a good way.
And you are supposed to pick one of them based on ninety minutes and a laminated marketing packet.
I have been on the other side of that table since 2000, so let me save you some time. The interview is not about whether you like the person. You will like most of us. The interview is about finding out who actually knows what they are doing before you hand them the biggest asset you own.
Here is what I would ask if I were you. And because it would be pretty gutless of me to write a list of hard questions and then not answer them, I answered every one of them myself on a separate page. Go check my work.
Before you take my word for anything, here is the record.
- 1,338+ homes sold and $532,653,786+ in career sales volume
- Average sold-to-list statistics over 101%
- Top 1% of Realtors nationwide, calculated against median member transaction volume published by the National Association of Realtors
- Master Certified Negotiation Expert (MCNE), one of five negotiation designations, and Pricing Strategy Advisor (PSA)
- Rookie of the Year, 2001, from both the Southern Maryland Association of Realtors and Long & Foster
- Maryland Associate Broker, license 531668, licensed since 2000
Production figures come from Bright MLS career production records, including data migrated from predecessor MLS systems. Past performance does not guarantee a specific result for any individual property.
I answered all ten of these in writing
Every question below, answered by me on its own page, with what a dodge sounds like underneath each one. Read my answers first, then go make two other agents answer the same list.
Question 1: "What do you need to know about me before you show me anything?"
Ask this first, before anyone opens a folder. It is the single most revealing question in the entire interview and it takes four seconds.
An agent who has done this work a long time will not have a price ready, because they cannot have a price ready. They have not seen your house. They do not know if you are moving for a new job in six weeks or thinking about next spring. They do not know if you are settling an estate with three siblings who disagree about everything. Every one of those facts changes the strategy.
An agent who came in with the number already printed prepared for a house, not for you.
The presentation starts immediately and it is about them. Awards, logos, a slide about their brokerage's global reach. You are selling a house in Calvert County. The global reach is not going to buy it.
Question 2: "What list price do you recommend, and show me how you got there"
Not what the price is. How they got there. Make them walk you through it.
You want to hear specific closed sales, and you want to hear why each one matters. You want adjustments explained out loud: this one had a finished basement and yours does not, this one backed to the road, this one sold in February when there were nine listings instead of three. You want to hear about the homes currently for sale, because those are what your buyer is actually choosing between.
You also want to hear the part nobody likes saying. Which comparable hurts you. What a buyer is going to object to. Every house has one. If an agent tells you your house has no weaknesses, they either did not look or they are managing you.
Price per square foot, used alone, as if that settles it. It treats a finished basement like a primary suite and a half acre on Route 4 like a half acre at the end of a private lane. It is the arithmetic people reach for when they have not done the analysis.
And if one agent's number is dramatically above the other two, ask that agent to show you the sales that support it. Not the vision. The sales. I wrote a whole page on why the highest number is usually the easiest number to give, because this is the thing that costs Southern Maryland sellers the most money and almost nobody warns them about it.
Question 3: "What is your sold-to-list ratio, and what is it measuring?"
The second half of that question is the one that matters. A percentage with no definition attached is a decoration.
Ask what time period it covers. Ask whether it counts listings that expired or were withdrawn, because leaving those out flatters the number considerably. Ask whether it is their personal production or the whole office. Ask if it includes the sales where they represented the buyer, which tells you nothing about how they price and market a listing.
Mine has stayed over 101% and it means homes closing at or above what we listed them for. Ask me to break it down and I will. Ask every agent to break it down. The ones who cannot will get vague fast, and the vagueness is your answer.
"Around 99, 100 percent, somewhere in there." Nobody who tracks their own numbers is fuzzy about them.
Question 4: "Have you pulled my deed?"
This one makes people blink, which is exactly why I love it.
Most agents do not look at title until the property is under contract and something ugly falls out. Then it is week three of a thirty day settlement, you are already packing, and there is an old mechanic's lien or a name on the deed that should have come off after a divorce in 2014, or the estate was never properly probated.
None of those are unfixable. All of them take time. Time you have plenty of before you list and none of once a buyer is waiting.
I pull the deed before we list. It takes me a few minutes and it has saved my sellers weeks.
"The title company handles that." The title company handles it when you are under contract. That is the whole problem.
Question 5: "What happens if we get no showings in the first two weeks?"
You are checking whether there is a plan or just optimism.
The right answer has a decision point in it, and it is specific. What gets reviewed, on what day, and what the options are. Showings, saves, online activity, agent feedback. And an honest statement of what each pattern means, because no showings and lots of showings with no offers are completely different problems with completely different fixes.
The wrong answer is "we will adjust as needed," which is a sentence that means nothing and commits to nothing.
The only plan is a price reduction, and it was clearly always the plan. If the strategy on day one already assumes a cut on day twenty one, ask why we are not just starting at the honest number.
Question 6: "Do you have actual negotiation credentials, or do you just say you are a good negotiator?"
Every single agent you interview is going to tell you they are a strong negotiator. Every one. It is the easiest claim in this business to make and the hardest for you to check.
So check it. Ask what training they have. Ask who issued it and when. Ask what they have taken since.
Here is mine, and you can verify all of it. I hold the Master Certified Negotiation Expert designation from the Real Estate Negotiation Institute, which is one of five negotiation designations I carry. I have negotiations coursework from Yale, Northwestern, UVA, Columbia and UC Davis. I am a Pricing Strategy Advisor, which is the National Association of Realtors designation specifically about building and defending a price. And I hold an Associate Broker license, which is a level above the salesperson license and requires additional education and experience to get.
I did not do all that because I collect letters. I did it because the contract and the negotiation are where sellers actually lose money, and I got tired of watching people improvise through the part that counts.
"I have been doing this twenty years, I do not need a class." Twenty years of repeating the same habits is not the same as twenty years of getting better. Ask what they have learned recently and watch what happens.
Question 7: "What about septic, well or Critical Area on this property?"
This is a Southern Maryland question and an agent who works here should not need a moment to think about it.
Septic records and permitted bedroom capacity. Well and water testing. Whether any part of the parcel sits in the Chesapeake Bay Critical Area, which affects what a buyer can do later with a deck, an addition, a pool or a shed. On the water, add the pier and the shoreline.
These are the items that detonate a contract three weeks in, after you have already picked out the house you are moving to. Deal with them before the sign goes up and they are paperwork. Deal with them after an inspection and they are leverage for the buyer.
A blank look, or "we will find out during the inspection." Finding out during the inspection means finding out when the buyer finds out, and now you are negotiating from behind.
Question 8: "Am I going to owe Maryland money at closing that I do not know about?"
If you have moved out of state, or you are selling an investment property, or you inherited the place and live in Ohio now, this question is worth real money.
Maryland withholds tax from the proceeds of nonresident sellers at settlement. As of 2026 that is 8.75% of the total payment for individuals, estates and trusts, and 8.25% for business entities such as LLCs, corporations and partnerships. You can apply for a reduced withholding on Form MW506AE, but it has to be filed at least 21 days before closing. If nobody mentions it until settlement, that opportunity is simply gone. I broke the whole thing down on Maryland nonresident seller withholding. And if the property is an investment, a 1031 exchange has to be set up before you close, not after. After is too late, permanently.
I am not your CPA and I am never going to pretend to be. But I raise both of these at the listing appointment, and I tell you to call your accountant while there is still time to do something about it. That is the whole job: know what you do not know, and say it early.
They have never heard of it. Or worse, they give you a confident answer about your taxes. An agent who plays tax advisor is telling you something important about their judgment.
Question 9: "Show me the marketing plan for my house. Not a sample."
Everyone has a marketing packet. The packet is beautiful. The packet is also identical for a $300,000 rambler and a $1.4 million waterfront property, which should tell you what it is worth.
Ask what happens for your house specifically. Which photos, shot when, and does this property need drone or video or a floor plan. What the listing copy will emphasize and what it will not claim. Where the paid promotion runs, to whom, for how long, and what the reporting looks like. What day it goes live and why that day.
"We syndicate to over 900 websites." So does everyone, automatically, because that is how the MLS feed works. That is not a marketing plan, it is a description of plumbing.
Question 10: "Who is actually going to be doing this? And who picks up at 8pm?"
Teams are fine. I run one. But you should know exactly who does what before you sign, not after.
Who sets the strategy. Who is at the showings. Who reads the offers and calls you about them. Who answers when you call on a Sunday because something scared you. If the person sitting at your table is not the person doing those things, that is not automatically wrong, but you deserve to know it now rather than discovering it in week two.
You never see the person who won the listing again. If the closer and the worker are different people and nobody told you, that was a choice they made about you.
Three things I do that most agents do not
Since I am asking you to interrogate everybody, here is where I would tell you I am different. Hold me to these.
1. I got the actual education
Anyone can say they are a negotiator. The question is whether there is anything behind it. MCNE from the Real Estate Negotiation Institute, one of five negotiation designations I hold. Pricing Strategy Advisor from NAR. Negotiations coursework at Yale, Northwestern, UVA, Columbia and UC Davis. Associate Broker rather than a salesperson license. Your contract and your negotiation are where the money is won or lost, and I wanted to be trained for that part instead of winging it.
2. I pull your deed before we list
Not after we are under contract. Before. Title surprises are cheap and boring in the four weeks before listing and expensive and terrifying in the four weeks before settlement.
3. I bring up 1031 and nonresident withholding at the kitchen table
Both have deadlines that arrive before your closing does, and both are unfixable once you have missed them. I raise them early and send you to your CPA with time to spare. I would rather have an awkward tax conversation in month one than watch a client lose real money in month three.
The bottom line
Interview three agents. Ask all of them the same questions. Take notes, because by Thursday they blur together.
And pay less attention to who gives you the best answers than to who gives you the most honest ones. The agent willing to tell you your kitchen is going to be a problem, or that your number is not there yet, is the one who is going to tell you the truth in week six when it actually costs something to say.
The best answer to any of these is never a smooth answer. It is a specific one.
Ask me all ten. I already wrote down my answers.
I put every one of these questions on its own page with my actual answers, including the ones agents dodge. Read them before you call me, so you can decide whether I am worth ninety minutes of your Saturday.
Ready to talk instead? Call or text 410-414-2438, email dawn@dawnriley.net, or schedule a consultation. Calvert, St. Mary's, Charles and Anne Arundel counties.
One necessary disclaimer. Nothing here is tax or legal advice, and I am not a CPA or an attorney. Maryland nonresident withholding and 1031 exchange rules change, and the amounts and deadlines that apply to your sale depend on facts specific to you. Verify current requirements with the Maryland Comptroller and talk to your own tax professional before you make a decision.
Frequently Asked Questions
Ask what they need to know about you before they show you anything. An agent who walks in with a price already printed prepared for a house, not for your situation. Timeline, reason for moving, whether an estate or a divorce is involved and what you are moving to next all change the strategy, and none of it fits in a packet made before they met you.
Tell them your goals, absolutely. But let each agent bring independent evidence first. If you lead with your number, you will hear your number repeated back to you three times, and you will have learned nothing about which agent can actually price a house.
It depends entirely on who is calculating it, which is why you have to ask. Find out the time period, whether expired and withdrawn listings are excluded, whether it is personal production or the whole office, and whether buyer-side sales are mixed in. Dawn Riley's average sold-to-list statistics have stayed over 101% per Bright MLS career production records, including data migrated from predecessor MLS systems, and she will break down what that covers on request.
Because title problems take time to clear and you have plenty of time before you list and almost none once a buyer is waiting. Old liens, a name that was never removed after a divorce, or an estate that was never properly probated are all fixable. They are just miserable to discover in week three of a thirty day settlement. Most agents never look at title until the property is under contract.
Every agent says they are a strong negotiator, so ask what actually backs it. Who issued the training, when, and what they have taken since. Dawn holds the Master Certified Negotiation Expert (MCNE) designation from the Real Estate Negotiation Institute, one of five negotiation designations, plus Pricing Strategy Advisor (PSA) from the National Association of Realtors and negotiations coursework from Yale, Northwestern, UVA, Columbia and UC Davis.
Septic records and permitted bedroom capacity, well and water testing, and whether the parcel sits in the Chesapeake Bay Critical Area, which limits what a buyer can add later. On the water, add the pier and shoreline. These are the items that blow up a contract after the inspection, and handling them before listing turns them from leverage into paperwork.
Then ask about nonresident withholding at settlement. As of 2026 Maryland withholds 8.75% of the total payment from individuals, estates and trusts, and 8.25% from business entities such as LLCs, corporations and partnerships. You can apply for a reduced withholding on Form MW506AE, which must be filed at least 21 days before closing. If the property is an investment, a 1031 exchange has to be set up before you close, not after. Dawn raises both at the listing appointment and sends you to your own CPA. Verify current requirements with the Maryland Comptroller.
Ask what happens for your house rather than what the company does in general. Which photos and when, whether the property needs drone, video or a floor plan, where paid promotion runs and to whom, what the reporting looks like and what day the listing goes live. “We syndicate to hundreds of websites” describes the MLS feed, which is automatic for every listing including your neighbor's.
A price well above the other agents with no closed sales behind it. It wins listings and then costs sellers money, because the plan behind that number is almost always the price reduction you will be asked for three weeks later.
Yes, and get specific. Who sets the strategy, who runs showings, who reads the offers and calls you about them, and who answers on a Sunday night. Teams work fine, but you should learn how yours is structured before you sign rather than in week two when the person who won your listing has moved on to the next appointment.
All ten are answered in writing on a companion page, with what a dodge sounds like under each one, plus the three things Dawn does that most agents do not: getting real negotiation credentials rather than just claiming to be a negotiator, pulling the deed before listing rather than after going under contract, and raising 1031 and nonresident withholding at the first appointment while there is still time to act.
About Dawn Riley
Dawn Riley is an Associate Broker, Realtor, Master Certified Negotiation Expert (MCNE) and Pricing Strategy Advisor (PSA) with The Riley Team at Deep Roots Real Estate in Huntingtown, Maryland. She holds Maryland license 531668, has been licensed since 2000, and has more than 25 years of real estate experience. She was named Rookie of the Year in 2001 by both the Southern Maryland Association of Realtors and Long & Foster, and has additional negotiations coursework from Yale, Northwestern, UVA, Columbia and UC Davis. Dawn combines strategic pricing, advanced property marketing and detailed Maryland contract knowledge to represent buyers and sellers throughout Calvert County and Southern Maryland.
Career results as of 2026: 1,338+ homes sold, $532,653,786+ in sales volume and average sold-to-list price statistics over 101%, per Bright MLS career production records, including data migrated from predecessor MLS systems. Production places her in the top 1% of Realtors nationwide, calculated against median member transaction volume published by the National Association of Realtors. Past performance does not guarantee a specific result for any individual property.
Dawn Riley
Associate Broker, Realtor, MCNE, PSA | MD License 531668
The Riley Team at Deep Roots Real Estate
2425 Solomons Island Rd., Suite C, Huntingtown, MD 20639
410-414-2438
dawn@dawnriley.net
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