How I Win Multiple Offers for Buyers in Southern Maryland
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In a competitive offer there is no coming up later. You get one look, and most buyers lose before the offer is ever written. This is how I plan and execute a multiple offer for my buyers in Calvert County and the rest of Southern Maryland, including the one concession that has won us more houses than money ever has.
You get one look
In a multiple offer, there is no second round. Not usually.
The seller sits down with their agent, reads the stack once, and picks. Nobody calls you to say your offer was close. Nobody invites you to try again. That is the whole event, and most buyers lose it before the offer is ever written, because they are still playing the game they read about online — come in reasonable, leave room to come up, see what happens.
There is no coming up. That is the part people cannot make themselves believe until they have lost two houses.
So I plan the entire scenario from the beginning. Before we tour anything, my buyers and I have already talked about what a competitive situation looks like, what we are willing to do in one, and what our real ceiling is. Not the comfortable number. The real one. When we find the house, we are not inventing a strategy under pressure at eight o'clock at night. We are executing one we built on a calm afternoon.
And we go in at our highest and best the first time. Every time.
What I want the seller doing at bedtime
I will tell you how I actually think about this, because it is not complicated.
I want the seller thinking about our offer the second it comes in. I want them still thinking about it when they go to bed that night. I want the rest of the stack to feel like paperwork they have to get through.
That happens when an offer is obviously written for them. Not a good generic offer. A targeted one. Most of the other contracts in that pile are not at their highest and best, and they do not show the seller how far that buyer is willing to work with them. They are a price and a set of defaults. Ours reads like somebody paid attention.
You cannot do that without knowing something about the people on the other side. Which is the actual work.
Finding out what the seller needs
Before I write anything, I call the listing agent. I have called this prospecting for information for as long as I have been doing it, and it is the least glamorous, highest-returning part of my whole process.
Every seller is weighing the same three things, and what changes from house to house is the order. The money. The calendar. And how confident they are that the deal will actually close.
So I ask about all three:
- Money. Are there offers already, and how high? Would your seller rather have a lower price with help toward their own costs? Is there personal property they would like handled outside the sale?
- Calendar. Short settlement or long? Do they need time in the house afterward? Is there a job start, a lease ending, or a contract on their next place driving this?
- Risk. Does your seller favor a preapproval over a prequalification? Does the loan type matter to them, and why? Is the appraisal a worry at this number?
- Anything else. My last question is always some version of: what else really matters to your seller here? That single question has produced more useful answers than the rest of the list put together.
I go first. I tell the listing agent something true and general about my buyers before I ask for anything, because a person who has just been given something feels the pull to give something back. That is not a trick. It is how people are built.
Some agents will not tell you a thing. Fine. Then I know I am writing partly blind, and I plan for that. But a surprising number will tell you plenty, and almost nobody bothers to ask. Information is the cheapest advantage in this business.
The two weeks that win houses
Here is the single most useful thing I have learned about competing for a house in Southern Maryland, and it has nothing to do with money.
Moving is miserable.
People forget that when they are looking at a stack of contracts. A seller is not just choosing a number. They are choosing what the next sixty days of their life feel like. If they have to be out of the house on the day they close, they are packing, closing, and unloading a truck inside one week, usually while working. If their next place is not ready, they are moving twice, into storage and back out. That is a genuinely awful thing to face.
So we write in a free two-week rent-back. The sellers close, they get their money, and they stay in the house two more weeks at no charge while they finish moving on a human schedule.
And in that same offer, the sellers buy a home warranty.
Those two terms travel together every time, and the reason is worth understanding. My buyer is giving up two weeks of possession they were not going to use anyway, and in exchange they get a year of coverage on the systems in a house they have just met. The sellers are paying a few hundred dollars for that warranty, and in exchange they get two weeks of their life back at the worst moment of the whole process. Both sides are handing over something cheap to them and valuable to the other. That is what a good trade looks like, and it is why neither side feels worked over.
If the house shows that they have taken real care of it, I do not ask for a security deposit on the rent-back either. The rent-back addendum already covers damage during the move-out, so the protection is written into the document. Asking a careful homeowner to also post a deposit adds very little real safety, and it changes the feeling of the whole offer from "we are trying to help you" to "we do not trust you." That feeling is worth more than the deposit.
Two weeks of peace of mind costs my buyer almost nothing and is invaluable to somebody staring down a move. We have won a lot of contracts on that pair — including ones where we were not the highest number on the table.
That is the whole principle in one example. Find the thing that costs your side little and is worth a great deal to theirs, and put it on the table early.
Everything else you can offer that is not price
Price is one line in a Maryland contract. There are dozens of others, and several of them are cheaper for you to give than money is.
- Closing cost help, in reverse. A buyer offering $495,000 with $10,000 toward the seller's costs can land that seller in nearly the same place as a clean $505,000, because no commission is paid on the credit. Same net, and a much easier appraisal. That trade wins houses.
- Earnest money. A larger deposit says you are serious. Making part of it non-refundable after contingencies are met says it louder. I only do that once my buyer is protected, never on day one.
- The settlement date. If my buyers can be flexible, that is free to give and sometimes decisive. If we are promising a fast close, I confirm the date with the lender before I write it, because a date you miss is worse than a date you never offered.
- The inspection. There is a wide range between waiving inspections entirely, which I do not recommend, and a normal inspection contingency. Inspecting for information only, or capping what we would ask a seller to repair, reduces their risk without leaving my buyer blind.
- Appraisal. Agreeing up front to cover a set amount above the appraised value removes the seller's biggest fear in a hot market. It only works if my buyer actually has that cash, and we check first.
Notice that none of those are about being tough. They are about knowing which terms carry real value and spending in the right place. More on that in every concession should buy something.
The escalation addendum, and the hundred dollar mistake
Maryland has a standard form for escalating a price above a competing offer, and used properly it is one of the strongest tools a buyer has. It lets you win at a price below your maximum instead of paying your maximum to find out whether you needed to.
But I see the same mistake constantly, and it drives me a little crazy.
The escalation is written to beat the best offer on the table by $100.
No seller is moving to your contract for $100. They are not moving for $1,000 either. Honestly, most are not moving for $2,000. You have just asked a family to change their decision, redo their thinking, and take on whatever unknowns come with your buyer, and you have offered them roughly the cost of a dishwasher to do it. It reads as a technicality, not as an offer. It can even irritate them.
If you want a seller's attention, the increment has to be big enough to feel like a real difference. Take our buyer's contract and we will give you $5,000 above the highest and best. That is the kind of number that makes a seller put the other contracts down.
And here is what buyers find reassuring once I explain it: on the Maryland form, the escalated price comes back to you as a counter-offer that you have to sign. The number can climb toward the ceiling you set, but it never lands on you without your pen touching the paper. You are in control the entire time. I go into the mechanics in the Maryland escalation addendum, explained.
And no, I am not going to lay out every technique I use with this form. A couple of them stay in my pocket, because that is part of what my clients are paying for. But I will sit down and show you precisely how I would use it on your deal.
How the offer arrives matters
A contract by itself is a stack of numbers from a stranger. The seller has no idea who you are, and what they cannot see, they treat as risk.
So we do not send a bare contract. We send a package: the contract, a short cover letter explaining why the terms are built the way they are, and something that makes my buyers real people with a real ability to close. A strong preapproval from a lender the listing agent has heard of. An invitation for the listing agent to call that lender directly, which surprisingly few buyers extend and which listing agents almost always appreciate.
The principle I follow is to include anything and everything that might possibly matter, and let the seller decide what counts. Do not make that judgment for them. The detail you almost left out is sometimes the reason you got the house.
More on building that in the offer package.
Present it to a human if you possibly can
When I started in this business, you hand-delivered an offer. You drove to the listing agent's office, you sat down with the seller in the room, and you presented it out loud.
Almost nobody does that now, and something real was lost. An email cannot read a room. It cannot notice a seller's face change at the word "June."
So I still ask. Not every time, but any time we are close and I need to understand what will actually secure the contract, I ask to present in person or on video. Plenty of agents say no. The ones who say yes are usually the ones who will also answer a question, and that half hour has won my clients houses that an email would not have. I go into what that used to look like in how real estate negotiation has changed.
Know who is working for you
I want to tell you something I see from the listing side, because it should affect who you hire.
On one of my listings we took in 27 offers. Seven of them simply appeared in my inbox with no phone call, no text, no heads-up of any kind. The agent sent a contract into the void and went back to their day.
One of those offers I found three weeks later, sitting in my spam folder. When I went back through the correspondence to see whether I had missed something, there was nothing. No email. No text. That agent's buyers never knew their offer was never read. They almost certainly assume to this day that they were beaten on price.
They were not beaten on price. They were beaten by their own representation.
So when you interview a buyer's agent, ask them what they do after they hit send. The answer should involve a phone call confirming the offer arrived, a conversation about what the seller needs, and a plan for staying in front of that listing agent while the decision is being made. If the answer is "I email it," you have learned something important.
Where buyers get stuck
Almost every buyer I have watched lose a house they wanted lost it the same way: they held something back for a second round that never came.
Sometimes it was money. More often it was smaller and sadder than that — a flexible settlement date they would have happily given, a repair cap they never thought to offer, two weeks of rent-back that would have cost them nothing.
The fix is not to overpay. It is to decide in advance what you are genuinely willing to do, find out what this particular seller actually needs, and then put all of it on the table the first time, because there is no second time.
That is the whole method. It is not aggressive and it is not clever. It is just prepared.
The forty-eight hours before we write
By the time I am typing a contract, most of the work is already done. Here is what happens in the two days before that, because this is the part buyers never see and it is the part that decides whether our offer is credible.
I call the lender and I actually talk to a person. Not to collect a letter — to find out how far along the file really is. There is a wide gulf between a buyer who filled in an online form and a buyer whose income, assets and credit have been through underwriting. Both of them can produce a piece of paper with the word "approved" on it. Only one of them can survive a nervous seller asking a hard question.
If my buyers are further along than most, I want the listing agent to know it, and I want them to be able to confirm it directly. So I ask the lender if they are willing to take a call from the other side, and I say so in the offer. Very few buyers extend that invitation. Listing agents notice it every single time.
I also want to know what we are walking into physically. If the home has a well and septic, those tests take scheduling, and a buyer who already has an inspector on standby can commit to a shorter due diligence window without gambling. If it is waterfront, the pier, the shoreline and the flood zone all raise questions that can slow a contract down later. Knowing the answers early lets us write tighter dates with confidence instead of hope.
None of that is negotiation in the way people picture it. All of it is why our offer reads as real.
When I tell a buyer not to do it
I would rather lose a deal than put a client somewhere they should not be, and competitive situations are where that comes up most.
If the number we would need to win is above what my buyer can comfortably carry, I say so out loud, and I say it before we are emotionally committed. Wanting a house badly is not a financing strategy. A buyer who stretches to win in April and cannot breathe by October did not get a good outcome, no matter what the contract says.
I will also tell a buyer to stop when the terms required to compete have stripped away the protections they actually need. Waiving an inspection entirely on a sixty-year-old house with a well and a septic system is not aggressive negotiating. It is buying a lottery ticket with your down payment. There are ways to reduce a seller's risk without going blind, and if a seller will only accept blind, that is information about the seller.
Losing a house hurts for about three weeks. The other thing hurts for years.
After you win
Winning the offer is the beginning of the transaction, not the end of it, and the way you won shapes the sixty days that follow.
This is the quiet argument for competing the way I have described. A buyer who won by being prepared, communicative and generous with the things that cost little arrives at the inspection with goodwill in the bank. A buyer who won by squeezing arrives with none. When something unexpected turns up in the crawlspace — and something usually does — those two buyers get very different responses from the same seller.
I have had sellers volunteer to fix things they were under no obligation to touch, simply because the whole process had been decent. That is not sentimentality. It is the practical return on not being difficult when you did not need to be.
Frequently Asked Questions
Usually not. In a competitive situation the seller reads the offers once and chooses, so there is rarely a second round. Going in at your highest and best terms the first time is the only reliable approach.
A rent-back lets the sellers stay in the home for a period after closing. Offering two weeks free gives a seller room to move on a human schedule, costs the buyer very little, and often matters more to them than a higher price.
Not always. The rent-back addendum already covers damage during move-out, so when a home has clearly been well cared for, skipping the deposit removes friction and makes the offer feel cooperative rather than suspicious.
Enough for the seller to feel a real difference. Beating the highest offer by $100, or even $1,000 or $2,000, rarely moves anyone. An increment such as $5,000 gets genuine attention.
No. On the Maryland form the escalated price returns to the buyer as a counter-offer that the buyer must sign and deliver, so the final price is always approved by the buyer.
Flexibility on the settlement date, a larger earnest money deposit, a cap on repair requests, appraisal protection, closing cost help structured in the seller's favor, and possession terms that suit the seller's move.
Enormously. Offers have been missed entirely because the buyer's agent never confirmed the listing agent received them. Ask any agent you interview what they do after they send an offer.
When the listing agent allows it, yes. Presenting in person or by video lets your agent learn what will actually secure the contract, which an emailed contract cannot do.
Thinking About Competing for a House?
Let us build your multiple offer plan before you find the house, not the night the offer is due. I will show you exactly what I would put on the table and why.
Dawn Riley
Associate Broker, Realtor, Master Certified Negotiator
The Riley Team at Deep Roots Real Estate
410-414-2438
dawn@dawnriley.net
https://dawnriley.net/