Don’t Blow the Deal: Ask These Questions Before Submitting Your Offer

Buying a home on Long Island in 2025 isn’t exactly a casual Sunday afternoon stroll through an open house. It’s more like trying to buy concert tickets to Taylor Swift—everyone wants in, prices are sky-high, and if you blink, it’s gone. So, before you throw your hat into the real estate ring and submit an offer, pause. Breathe. And ask the right questions. Because making a smart offer is how you win the house and sleep at night—with your HVAC intact and your taxes semi-sane.

What’s the Seller’s Motivation?

Are they relocating for work? Downsizing? Or did they just binge-watch HGTV and now want to "try something new in Vermont?" Understanding the seller’s motivation can help you craft a more compelling offer—whether that means flexible closing terms, a lease-back, or simply not asking them to fix that cracked tile in the bathroom. In a market with more eyes than inventory, reading between the lines matters more than ever.

How Competitive Is the Market Right Now?

Spoiler: it’s still hot, but not everything’s flying off the shelves like it did in 2021. Look at current comps, days on market, and ask if the listing has had price reductions or multiple offers. In Nassau and Suffolk, neighborhood dynamics shift faster than LIRR delays. Garden City might be booming while Massapequa chills for a minute. You don’t want to show up to a poker table with Monopoly money.

Are There Any Recent or Upcoming Assessments or Repairs?

Because nothing says "fun" like finding out the basement floods every March. Ask about roof age, HVAC systems, foundation issues, and whether the home has had any recent or pending repairs. In 2025, repair costs are up 18% over pre-pandemic levels, and contractor delays are real. If it’s a condo or co-op, check for special assessments—because surprise bills are not the kind of excitement you're looking for.

Have There Been Other Offers? If So, What Happened?

Sometimes, a house has seen multiple buyers come and go. Find out if previous offers fell apart due to financing, inspection, or if the seller suddenly decided they were emotionally attached to their kitchen backsplash. This gives you leverage and insight—and possibly a good story.

Are There Red Flags in the Disclosure?

Take your time combing through that disclosure form. If you spot anything sketchy—like mold, leaks, or mysterious "past repairs" without documentation—it’s worth asking for more details. Or at least bringing a flashlight and a healthy amount of skepticism to the home inspection. Mold isn’t a vibe. Neither is asbestos.

What’s the Appraisal Risk?

In fast-rising markets like Garden City or Merrick, there’s always the risk of offering over asking... and then watching the appraisal come in light. Know the comps, talk to your agent, and be ready with an appraisal gap strategy if you’re playing that game. Because nobody wants to explain to Grandma why you're backing out of escrow.

What’s the Exit Strategy?

We don’t love to talk about this, but it matters. If you had to resell the house in 3-5 years, would it hold value? Is it in a flood zone? Is the town planning major infrastructure changes or school rezoning? Think ahead—your future self (and your future budget) will thank you. Especially when you're staring at that cracked driveway wondering where it all went wrong.

What Does the Property Tax History Look Like?

Taxes on Long Island aren’t just high—they’re practically an Olympic sport. Get a record of recent tax bills and look for unexpected jumps or looming reassessments. Nassau’s reassessment plans and Suffolk’s storm infrastructure bonds can swing your tax bill hard. Better to know now if your mortgage payment is about to balloon from "manageable" to "we’re eating ramen until 2030."

How Walkable or Drivable Is the Location, Really?

That dreamy listing near the "village center" might actually mean a 15-minute drive and a parking nightmare. Use maps and your feet—check access to coffee shops, groceries, and public transit. With gas prices creeping past $4 again and LIRR still being... LIRR, this question can make or break daily sanity.

What Are the Homeowners Association Rules (If Any)?

If the house is part of an HOA, ask to see the rulebook—and then brace yourself. From flag restrictions to approved lawn colors (yes, really), HOA policies can kill the vibe if you’re not ready. Know what you're getting into before you move into a Stepford scenario. Your golden retriever deserves better.

About to make an offer? Let’s make sure it’s the right one.

Submitting an offer isn’t just paperwork—it’s strategy, psychology, and a little bit of poker. Asking the right questions up front saves you time, money, and heartache—and keeps you from buying the prettiest money pit on the block.

I’m Dean Miller, Long Island’s only AI-certified real estate agent.
Whether it’s your first bid or your fifth, I’ll help you play smarter, not just harder.

Text me before you hit "send" on that offer. Seriously. You’ll thank me later—maybe even buy me a bagel. Just not from a chain store. This is Long Island. We have standards.