Jenna Levin August 31, 2026
Almost every buyer I work with walks into their first multiple offer situation thinking the same thing. Whoever offers the most money wins. Sometimes that's true. A lot of the time, it isn't, and I've watched buyers lose homes to an offer that was actually lower than theirs, because the seller had reasons to trust the other offer more.
Price gets all the attention because it's the easiest number to compare. But sellers, and the attorneys and agents advising them, are reading the whole offer. Here's what else is actually in play.
Your deposit size.
In Massachusetts, your initial deposit comes in with the offer, and a larger second deposit typically follows once the Purchase and Sale Agreement is signed. A buyer putting down a meaningful deposit is signaling something. This isn't a maybe. That matters to a seller who's about to take their home off the market and turn down other offers to accept yours.
How clean your contingencies are.
Every offer has some combination of inspection, financing, and sometimes appraisal contingencies. None of that is wrong to include, and the goal is never to waive protections you're not comfortable losing. But there's a real difference between an offer with a tight, clearly defined inspection window and one that leaves the timeline vague or stacks on extra conditions. Sellers read a clean, well structured contingency section as fewer places for the deal to fall apart later. That reads as confidence.
Your closing date flexibility.
This one gets overlooked constantly. Some sellers need to close fast. Others need extra time to find their next place and would love a rent back arrangement that lets them stay in the home for a few weeks after closing. Asking your agent what the seller's timeline actually looks like, instead of defaulting to a standard 30 or 45 days, can make your offer feel like it was written for that seller specifically, not copied from the last one.
How prepared your financing looks.
There's a real gap between a pre-qualification letter and a full underwritten pre-approval, and sellers' agents know the difference immediately. A buyer whose financing has already been through underwriting is a buyer with far less risk of a financing surprise mid contract. If you haven't gotten that far with your lender yet, it's worth doing before you're competing for a home you actually want.
How the offer is written.
An offer with a lot of extra asks, small credits, unusual terms, odd deadlines, tends to read as a buyer who's going to be difficult to get through closing. A straightforward offer, even at the same price, often reads as the safer, easier transaction. Sellers are choosing who they want to go through the next month and a half with, not just the biggest check.
None of this means price doesn't matter. It does. But in a competitive offer situation, price is one lever out of several, and the buyers who understand that are usually the ones who end up with the keys.
If you're getting ready to write an offer and want to talk through how to structure it for the home you're actually competing for, I'm always happy to walk through it with you.
617-970-5144
Warmly, Jenna Levin
Stay up to date on the latest real estate trends.
Farmers markets, pond days, and the unscripted reasons families put down roots here.
It's not about who has the most money, it's about who has the clearest strategy.
The Neighborhood Insider for Natick, Needham, Newton and Wellesley
Etiam non quam lacus suspendisse faucibus interdum. Orci ac auctor augue mauris augue neque. Bibendum at varius vel pharetra. Viverra orci sagittis eu volutpat.