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The Waterfront Questions Every Southern Maryland Seller Should Ask, and My Answers

The Waterfront Questions Every Southern Maryland Seller Should Ask, and My Answers

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A Southern Maryland waterfront property at the shoreline with a pier reaching into the water
Dawn Riley, Associate Broker, Realtor, Master Certified Negotiation Expert and Pricing Strategy Advisor with Deep Roots Real Estate

I told waterfront sellers what to ask an agent. Here is every one of those questions answered by me, in writing.

BACK TO THE GUIDE

I wrote a guide telling Southern Maryland sellers what to ask a waterfront agent. Publishing that and then not answering any of it myself seemed like a bad look.

So here is the whole list with my answers. Under each one I put what a dodge sounds like, because on waterfront the difference between an agent who knows and an agent who is enthusiastic is usually audible within about two questions.

Where I am coming from.

  • Nearly 100 Maryland waterfront sales, and more than 40 years living in Calvert County and on the water
  • 1,338+ homes sold, $532,653,786+ in career volume, sold-to-list over 101%
  • Top 1% of Realtors nationwide, calculated against median member transaction volume published by the National Association of Realtors
  • MCNE, one of five negotiation designations, and PSA, plus negotiations coursework at Yale, Northwestern, UVA, Columbia and UC Davis
  • Maryland Associate Broker, license 531668. Verify it here.

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.

The waterfront questions, and my answers

"How many waterfront properties have you sold, and on which water?"

Nearly 100 across my career, and I have lived in Calvert County and along the water for more than 40 years. That second part matters more than people assume, because the differences here are local down to the creek.

The Bay is not the Patuxent. The Patuxent is not a protected creek off St. Leonard. Exposure, wind, boat traffic, depth and what a pier can be permitted to do all change from one to the next, and pricing them the same way produces confident nonsense.

What a dodge sounds like

All the examples come from one narrow slice of water, or from ten years ago. Both the rules and the buyers have moved since.

"How do you price the water separately from the house?"

As separate line items, because that is how buyers actually value it.

Lot orientation and what you look at. Whether the shoreline is usable or a bank nobody can get down. Water depth at the pier at mean low water, not at whatever moment I happened to stand on it. Pier condition and whether the lift works. Privacy from the neighbors. Flood exposure and what insurance is likely to cost. Then the house.

Two homes with identical square footage a mile apart can be a quarter million dollars apart, and none of that gap is explained by the kitchens.

What a dodge sounds like

Price per square foot, or comparables pulled by radius. A one mile circle around your house is full of properties with nothing in common with it.

"Will you advertise deep water, navigable or permitted pier?"

Only if I can show you the paper. Those are material claims, not adjectives.

If a buyer spends money on inspections and a survey and then finds out the pier was never permitted, that is not an awkward moment. That is a legal problem, and it is your legal problem more than mine. So I go find the records first. If I cannot verify it, it does not go in the listing, even when the previous owner is completely certain.

What a dodge sounds like

"It has been there thirty years, it is fine." Age is not a permit and neither is the absence of complaints.

"What do I need to know about the Critical Area?"

That most tidal waterfront in Calvert County is inside it, and that your buyer is going to ask.

In practice it governs the buffer near the water, what vegetation can come out, how much of your lot can be covered by impervious surface, and what mitigation is required to change any of that. Which lands directly on the buyer who is standing in your yard mentally building a pool, an addition, a bigger deck or a pole barn.

I can explain the framework and I can tell you where to get a real answer. What I will not do is tell you what your buyer can build, because nobody knows that without the county reviewing the actual parcel.

What a dodge sounds like

A confident answer about what can be built. That agent is guessing with your liability.

"What about flood zone and insurance?"

I want it settled before we list, not during a buyer's financing.

Flood zone from the FEMA Flood Map Service Center, the elevation certificate if one exists, and a realistic sense of what a buyer will pay for coverage. Because insurance cost is part of what your buyer can afford, which means it is part of your price whether anyone acknowledges it or not.

Handing a buyer this information up front is far better than having them discover it in week three and use it on you.

What a dodge sounds like

Nobody mentions flood insurance until the buyer's lender does.

"What are you going to check on the pier?"

Permits and approvals first. Then pilings, decking, and any electrical or water service running out there. Lift capacity and whether it actually operates. Depth at the end at mean low water. Whether the shoreline is stable, eroding, or has living shoreline or bulkhead work, and whether that work was permitted.

And somebody walks it with a flashlight, which sounds obvious and frequently does not happen. Marine construction is specialized, expensive and slow to permit, so a pier problem found during the buyer's inspection is a large negotiation rather than a small one.

What a dodge sounds like

The pier is described in the listing copy and nobody has been on it.

"Is my septic going to be a problem?"

On waterfront it deserves a look every time. These lots are frequently constrained and the systems are frequently older.

I want the permitted bedroom capacity, where the reserve area sits, and a realistic view of what replacement would involve on a lot with a buffer and setbacks. The expensive mistake is advertising four bedrooms on a three bedroom septic permit, which is a correction you very much want to make before the listing goes live.

What a dodge sounds like

The bedroom count came off the tax record and nobody compared it to the septic permit.

"How will you actually market it?"

Drone from above and from the water, so a buyer scrolling on a phone immediately understands how the house, the shoreline and the pier relate to each other. Stills shot when the light on the water is right, which is a narrow window and not the middle of the day.

Copy that is specific and verified. Orientation, what you genuinely see, what the access actually is. Waterfront buyers are sophisticated and vague superlatives make them suspicious, which is the opposite of what you are paying for.

What a dodge sounds like

Interior photos and one aerial shot at noon in flat light. Somebody bought the cheap package for an expensive house.

"What is on my title that could slow this down?"

I pull your deed before we list, and on waterfront there is usually more to find.

Riparian rights, easements, shared pier or shared access agreements, access strips, and old boundary questions all live on the title. Every one of them is easier to sort out in the weeks before listing than during a thirty day settlement with a buyer waiting and a moving truck booked.

What a dodge sounds like

"Title will catch that." They will, once you are under contract, which is exactly the wrong time.

"Am I going to get surprised on taxes at closing?"

Waterfront owners are often second-home owners, investors, or people who moved away years ago, and all three of those have tax consequences with deadlines that hit before closing.

If you are not a Maryland resident, Maryland withholds tax from your proceeds 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. A reduced withholding can be requested on Form MW506AE, filed at least 21 days before closing. I broke the whole thing down on Maryland nonresident seller withholding. If this is an investment property and you want a 1031 exchange, it has to be set up before you close. After is permanently too late.

I am not a CPA and will not act like one. I raise both at the first meeting and send you to your accountant while there is still time to do something.

What a dodge sounds like

Never heard of it, or a confident answer about your taxes from someone with no license to give one.

Three things I do that most agents do not

1. I have the credentials, not just the affection for the view

Every agent loves your water. That is a normal human response, not a qualification. MCNE from the Real Estate Negotiation Institute, one of five negotiation designations I hold. PSA from the National Association of Realtors. Negotiations coursework at Yale, Northwestern, UVA, Columbia and UC Davis. Associate Broker rather than a salesperson license. Waterfront contracts have more moving parts and more places to lose money, and I wanted to be trained for that instead of improvising.

How to verify it

Designations come from named organizations and can be confirmed. My license is 531668, public at the Maryland Department of Labor. Check every agent you interview.

2. I pull your deed before we list

Especially on the water, where riparian rights, shared pier agreements and access easements turn up regularly. Finding them early is paperwork. Finding them during settlement is a crisis with a deadline.

What to ask for

Ask your agent to pull the deed and tell you what they found. If that happens later in their process, you have learned something useful.

3. I raise 1031 and nonresident withholding at the first meeting

Both have deadlines that land before closing and neither can be fixed afterward. I cannot advise you on either one, and I can absolutely make sure you know they exist while there is still runway to act.

What to ask for

If you live out of state or this is an investment property, raise it at the first appointment, then call your own tax professional.

Take this to somebody else too

Bring this page to two other waterfront listing appointments. If another agent answers it better than I did, hire them. I mean that, and I would rather you sell well than sell with me.

What I am sure of is that these are the right questions, and that most waterfront sellers are never told to ask them.

Let's walk your shoreline

I will look at the pier, pull your deed, check the flood and Critical Area picture, read the septic capacity and give you a supported range with the evidence attached. Plus what would move the top of that range before we list.

Schedule a waterfront consultation

Call or text 410-414-2438 or email dawn@dawnriley.net. Calvert, St. Mary's, Charles and Anne Arundel counties.

Necessary disclaimer. Nothing on this page is tax, legal, engineering or insurance advice. Critical Area rules, flood maps, pier permitting, septic capacity and Maryland nonresident withholding all change, and what applies to your parcel depends on facts specific to it. Confirm Critical Area and permitting questions with Calvert County or the appropriate county office, flood information through the FEMA Flood Map Service Center, and tax questions with the Comptroller of Maryland and your own CPA.

Frequently Asked Questions

About Dawn Riley

Dawn Riley, Associate Broker and Master Certified Negotiation Expert with The Riley Team at Deep Roots Real Estate
Dawn Riley, Associate Broker, Realtor, Master Certified Negotiator and Pricing Strategy Advisor

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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