A Winning Offer Isn’t Always the Highest Offer
There’s a misconception in real estate that getting a home under contract is simply a matter of offering the most money. And while price certainly matters, I’ve seen enough transactions to know that the highest offer isn’t always the one a seller chooses.
Sometimes a seller needs to close quickly. Sometimes they’re more concerned about a transaction falling apart than squeezing every last dollar out of the sale. Other times, they’re overwhelmed by the prospect of moving and would gladly accept an offer that makes their lives a little easier.
Understanding those priorities can be just as important as understanding the property’s market value.
When I’m representing a buyer, I don’t approach the transaction as a competition to see who can offer the most money. I approach it as an opportunity to understand what matters to both parties and structure an offer that gives my client the strongest possible position without unnecessarily compromising their interests.
That takes research, relationships, communication, and a willingness to think beyond the standard terms of a purchase and sale agreement.
Here’s how I approach it.
1. I Start by Understanding the Seller’s Motivation
Before we write an offer, one of my first steps is to call the listing agent.
And I don’t just ask whether there are other offers.
I want to understand the seller’s situation, their priorities, and what an ideal transaction might look like from their perspective. Of course, the listing agent can only share what the seller has authorized them to disclose, but even a conversation about preferred terms can be incredibly helpful.
What’s motivating the sale?
Are the sellers relocating for a job? Have they already purchased another property? Are they downsizing after decades in the same home? Is the property vacant, or are they still figuring out where they’re going next?
More importantly, what matters most to them?
I generally think about seller motivation in four categories:
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Timeline: Does the seller need a quick closing, or would they benefit from additional time to move?
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Net proceeds: Is maximizing the amount they walk away with their highest priority?
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Certainty: Are they particularly concerned about financing, contingencies, or the risk of a transaction falling apart?
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Convenience: Would a simpler moving process, fewer logistical demands, or more flexibility make the transaction more appealing?
The answers can influence how I recommend structuring an offer.
A seller who’s already moved out may appreciate a quick, straightforward closing. Someone who’s lived in their home for thirty years might need more time and flexibility. And a seller who has experienced a failed transaction may place a particularly high value on a buyer who appears well prepared and financially qualified.
Not every seller has the same definition of a successful sale.
My job is to understand those differences and identify opportunities that benefit my buyer.
2. I Look for Ways to Make the Transaction Easier
One of my favorite parts of real estate is finding solutions that don’t necessarily cost my client more money.
Sometimes a little flexibility can make an offer significantly more appealing.
For example, imagine a seller who’s downsizing from a large farmhouse. They’ve accumulated decades of belongings, and the prospect of getting everything out before closing feels overwhelming.
If my buyer is comfortable with it, we might explore allowing the seller to leave certain agreed-upon items behind rather than requiring the property to be completely emptied.
Maybe the seller has old shelving in the basement, leftover building materials in the garage, or furniture they don’t want to move.
A buyer who plans to renovate or has the resources to handle those items might be willing to take on that responsibility.
The same goes for the condition in which a property is delivered.
Traditionally, sellers are expected to remove their belongings and leave the home in the condition required by the contract, often described as broom-swept or broom-clean.
But if a buyer is comfortable accepting a property without that level of cleaning, and the arrangement is clearly documented, it could remove another source of stress for the seller.
That doesn’t mean I recommend buyers agree to anything and everything.
We need to be thoughtful about what they’re accepting, including potential removal costs, disposal issues, and the condition of the property.
But when there’s an opportunity to offer convenience without meaningfully increasing my client’s risk or expense, I think it’s worth exploring.
Sometimes the most valuable thing you can offer a seller isn’t another $5,000.
It’s one less thing they have to worry about.
3. I Understand That Certainty Has Value
A seller doesn’t just want to accept an offer. They want to get to the closing table.
And those are two different things.
An offer can look fantastic on paper, but if the buyer isn’t financially prepared, the contingencies are poorly considered, or the timeline is unrealistic, the seller may see more risk than reward.
That’s why I put so much emphasis on preparation before my buyers ever make an offer.
I want them to understand their financing, their budget, the property they’re purchasing, and the obligations they’re taking on.
If they’re obtaining a mortgage, I want them working with a responsive lender who understands the transaction and can provide appropriate documentation of their qualifications.
I also want to understand the property-specific considerations that could affect the purchase.
In Vermont, that might mean private wells, septic systems, shared roads, wastewater permits, or unusual ownership arrangements.
The goal is to identify potential complications early, rather than discover them after we’re under contract.
Strong Doesn’t Have to Mean Reckless
There’s an important distinction between making a competitive offer and taking unnecessary risks.
I don’t believe buyers should automatically waive inspections, financing protections, or other important contingencies just because a market is competitive.
Those protections exist for a reason.
Instead, I look at whether we can make the terms clear, practical, and realistic while preserving the safeguards my client needs.
Sometimes that means being flexible with timing. Sometimes it means having financing documentation organized before submitting the offer. Sometimes it’s as simple as ensuring every deadline is achievable.
A well-prepared buyer can be attractive to a seller without taking on risks they don’t fully understand.
4. I Build Relationships With Listing Agents Before We Need Something
Real estate is a relationship business, and that doesn’t change when I’m representing a buyer.
I believe communication between agents can have a meaningful impact on how smoothly a transaction progresses.
When I contact a listing agent, I’m not simply checking a box. I’m trying to establish a productive working relationship.
I ask questions, listen carefully, and make sure I understand the seller’s priorities and the property’s circumstances.
If the listing agent shares that the seller is worried about a complicated closing or has specific logistical concerns, I want to know that before writing the offer.
And if there’s something unusual about the property, I’d rather discuss it proactively than discover it through a series of emails after the offer has been submitted.
I Want the Listing Agent to Know I’m Accessible
One of the simplest things an agent can do is also one of the most important: respond.
I return calls. I communicate clearly. I follow through when I say I’m going to do something.
If there’s a question about financing, a contract term, or my buyer’s intentions, I want the listing agent to feel comfortable reaching out.
That doesn’t mean we’re always going to agree. Negotiations are negotiations, and my responsibility is to represent my buyer’s interests.
But professionalism and collaboration aren’t weaknesses.
They’re part of getting things done.
And when a listing agent is presenting multiple offers to a seller, confidence in the people on the other side of the transaction can matter.
5. I Don’t Just Submit an Offer. I Present It.
Imagine you’re a seller reviewing several offers.
One arrives as a collection of attachments with little explanation. Another comes with a clear summary outlining the price, financing, proposed closing date, contingencies, and any terms designed around your priorities.
Which one is easier to evaluate?
When I submit an offer, I want the listing agent to be able to understand and communicate its strengths without having to hunt through pages of paperwork.
That means providing a concise, organized presentation of the terms.
I typically highlight the purchase price, deposit, financing details, proposed closing timeline, contingencies, and any flexibility we’ve included.
If we’ve structured the offer to accommodate something important to the seller, I make that clear.
For example, if the listing agent told me the seller would benefit from a longer closing period, I might explain that we’ve intentionally proposed a timeline that accommodates their move.
Or if the seller is concerned about removing certain belongings, I can highlight an agreed-upon arrangement that makes that easier.
I’m not trying to overwhelm anyone with a sales pitch.
I’m making sure the seller and their agent can quickly understand what we’re offering and why it deserves consideration.
I Want the Offer to Tell a Clear Story
Every offer has numbers and legal terms.
But the strongest presentations also provide context.
Why does this timeline work? How is the buyer prepared to move forward? What aspects of the transaction have we already addressed? How do the terms respond to the seller’s stated priorities?
A little explanation can make an offer feel more intentional and easier to evaluate.
And in a competitive situation, clarity is an advantage.
6. I Share What My Buyer Loves About the Property
There’s another detail I like to include when appropriate: a little about what drew my buyer to the home.
Not a lengthy personal letter. Not a story about their family, background, or anything that could introduce Fair Housing concerns into the decision-making process.
Instead, I focus on the property itself.
Maybe my buyer loves the original woodwork in an antique Vermont farmhouse. Maybe they’ve been searching for a home with enough acreage to garden. Perhaps the layout is ideal for their needs, or they appreciate the care the seller has put into maintaining the property.
Those are details worth sharing.
A seller who’s spent years restoring a historic home might appreciate knowing that a prospective buyer recognizes the craftsmanship.
Someone who’s carefully maintained a property may be pleased to hear that those improvements haven’t gone unnoticed.
Of course, sellers should evaluate offers based on their terms and other lawful considerations, not a buyer’s personal characteristics.
But there’s nothing wrong with communicating genuine enthusiasm for the property.
I think it adds a human element to a process that can otherwise feel very transactional.
7. I Make Sure My Buyers Understand the Entire Offer
Before an offer goes to the listing agent, my buyers need to understand what they’re agreeing to.
Not just the purchase price.
I want them to understand the deposit, financing terms, contingencies, deadlines, closing costs, and what happens if an issue arises during the transaction.
We also discuss how different terms could affect their negotiating position.
For example, a faster closing might appeal to the seller, but only if it’s realistic for the buyer’s lender and other transaction requirements.
Agreeing to accept leftover personal property might help the seller, but it could also create expenses or complications for the buyer.
And offering a higher price may not always be the most effective way to improve an offer, particularly if appraisal or financing considerations become relevant.
My responsibility is to help my buyers understand the tradeoffs so they can make informed decisions.
I want them to feel confident about their offer, whether it’s accepted or not.
8. I Stay Proactive After the Offer Is Submitted
Submitting an offer isn’t the end of the negotiation.
Sometimes the listing agent has follow-up questions. Sometimes the seller wants clarification about a particular term. Sometimes circumstances change, or there’s an opportunity to adjust an offer before a final decision is made.
I stay available and engaged.
If the listing agent needs additional information about financing, I work with the buyer and lender to provide appropriate clarification.
If a seller is concerned about timing, I explore whether there’s flexibility.
If another offer enters the picture, I help my buyer evaluate whether changing our terms makes sense.
What I don’t do is disappear after emailing the paperwork and hope for the best.
I believe proactive communication demonstrates that we’re serious, organized, and prepared to move forward.
And if our offer isn’t selected, I try to learn what I can from the outcome.
That feedback can be valuable as we refine our approach to the next property.
9. I Negotiate With the Entire Transaction in Mind
It’s easy to become focused on winning an individual negotiation.
But my goal isn’t simply to get an offer accepted at any cost.
It’s to help my buyer purchase the right property, on terms that make sense, and successfully get to closing.
That requires thinking beyond the initial offer.
A contract with unrealistic deadlines or poorly considered terms can create problems later. A concession that seems minor during negotiations may have a significant financial impact once the transaction is underway.
I want to understand not just how an offer will be received today, but how the transaction is likely to unfold over the following weeks.
This is particularly important in Vermont, where property-specific issues such as septic documentation, private road agreements, title questions, and older homes can introduce additional considerations.
When we anticipate those issues and communicate clearly, we’re in a better position to address them without unnecessary surprises.
10. My Approach Is Strategic, But It’s Also Personal
I’ve spent years working in real estate, including leading large organizations and consulting with agents across the country.
That experience has shaped how I think about negotiations, communication, and the details that influence successful transactions.
But I’ve also made a deliberate decision to work directly with my own clients.
When you’re buying a home with me, you’re working with me.
I’m the person helping you evaluate the property, understand the market, think through the offer, and communicate with the listing agent.
I don’t believe in a one-size-fits-all offer strategy because no two buyers, sellers, or properties are exactly alike.
Some transactions require creativity. Others require patience. And sometimes the most effective approach is simply a well-supported price, reasonable terms, and excellent communication.
What matters is understanding the situation and responding thoughtfully.
Getting a Vermont Home Under Contract Takes More Than a Good Price
There will always be transactions where the highest price wins. There will also be situations where a seller has very specific priorities that no amount of creativity can overcome.
I can’t guarantee that every offer I write will be accepted.
But I can control how prepared we are, how thoughtfully we structure the offer, how clearly we communicate its strengths, and how professionally we approach the people on the other side of the transaction.
I believe those details matter.
When I represent a buyer, I want the seller and listing agent to see more than a number on a contract. I want them to see a serious, well-prepared buyer, a thoughtful offer, and an agent who’s committed to making the process work.
Because sometimes the difference between an offer that’s accepted and one that isn’t comes down to understanding what the seller actually needs, and finding a way to deliver it.
If you’re thinking about buying a home in Vermont, I’d love to help you approach the process with a strategy that goes beyond simply deciding how much to offer.
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Erin McCormick | Realtor, Keller Williams Vermont
Founder, Travel Like a Local® Vermont | Live Local Vermont