Don’t Let Zillow Pick Your Real Estate Agent (And Don’t Trust That Payment Pie Chart Either)

If you’ve ever opened Zillow “just to browse” and suddenly found yourself scheduling a showing… welcome to what I call the Zillow itch.

It happens fast:

• You see a house you love

• You peek at the little payment pie chart

• You think, “Okay cool, I can do that”

• You click Request a tour

• And now you’re on the phone with an agent you didn’t choose

Here’s the problem: that path is one of the worst-case scenarios for homebuyers — and I see it play out all the time.

I’m Chelsea Winstead — a mortgage broker and home-financing strategist — and I help buyers build a plan before they fall in love with a house they can’t comfortably buy.

Let’s walk through what Zillow gets wrong, what the real process should look like, and how to set yourself up to win (without turning your home purchase into a stress-fueled circus).

Why “Request a Tour” Can Backfire

When you click that button, Zillow connects you with an agent — often based on routing and lead distribution, not “best fit.”

What happens next is the part buyers don’t see coming:

• You meet the agent in person

• You tour a home

• You sign paperwork (sometimes without realizing what it is)

• And now you may be locked into working with an agent you don’t even like

This isn’t about villainizing agents. There are great agents out there.
It’s about how you choose one.

Because Zillow choosing your agent is like letting a vending machine pick your therapist. Convenient? Sure. Ideal? Absolutely not.

The Zillow Payment Pie Chart Problem (Why It’s Usually Wrong)

That “estimated monthly payment” is often misleading because it commonly assumes things that don’t match reality.

1) Zillow often defaults to 20% down

Most buyers today are not putting 20% down — especially first-time buyers.

So from the start, Zillow may be showing you a payment based on a down payment you’re not actually using.

2) Property taxes are often off

Taxes vary wildly by:

• county

• homestead exemptions

• reassessments after purchase

• whether it’s primary vs second home

Zillow’s estimate can be close… or wildly wrong.

3) Homeowners insurance is often off

Insurance depends on:

• zip code and risk factors

• rebuild cost (not purchase price)

• wind/hurricane zones

• claims history

• deductible choices

So if your insurance is underestimated, your payment is understated.

Result: buyers fall in love with a home thinking it’s affordable — then later find out it’s not what they expected.

And yes: it hurts your feelings.

The Real Homebuying Order of Operations (The One That Works)

Here’s the truth:
A real estate agent cannot help you buy a home if you can’t finance it — unless you’re paying cash.

Most people aren’t cash buyers.

So the proper process is:

Step 1: Talk to a financing professional first

A lender (or mortgage broker like me) helps you determine:

• credit score impact

• income and job history requirements

• available loan options

• down payment and cash-to-close

• realistic monthly payment

• realistic purchase price

This is not an extra step.
This is the first step.

And no — it doesn’t cost you anything.

Mortgage professionals and agents are typically paid at the end of the transaction. You’re not writing me a check out of your personal checking account just to run numbers.

Step 2: Start with your monthly payment and back into purchase price

This is how I run my process with clients.

Because “what you qualify for” and “what you can comfortably afford” are not the same thing.

And your payment depends on location:

• South Florida ≠ Maryland

• Different taxes, insurance, home prices, HOAs, etc.

So instead of letting Zillow tell you what your life costs, we start with:
What payment feels good for you?
Then we reverse-engineer the price point.

Step 3: Get an underwritten pre-approval (not a flimsy pre-qual)

In today’s market, especially in competitive areas, you want an approval that holds weight.

Here’s the difference:

Pre-qualification: basically vibes + a quick glance
Pre-approval: a lender reviews your info and runs it through underwriting systems
Underwritten pre-approval: your file is actually reviewed by underwriters before you offer

That last one is the one that matters — because underwriting is where surprises show up.

For my clients, underwritten pre-approval is the standard.
We don’t submit offers without it — especially in competitive pockets like Maryland, Virginia, DC, Pennsylvania, and other hot markets.

Because submitting an offer without a strong approval is like showing up to a job interview without a resume and hoping your personality carries you. (Sometimes it does. Usually it doesn’t.)

Step 4: Choose your agent intentionally (and yes, I help with that)

After we know your numbers and you’re fully positioned, then you need the right agent — not whoever answered Zillow first.

What I do for my clients:

• I interview you on what matters (communication style, values, personality traits)

• I look at real production and performance (not marketing)

• I match you with a strong buyer’s agent in your target area

• I avoid “giant teams” when possible so you get a more personal experience

Why? Because your lender + agent is your delivery team.
If they’re not aligned, your “plan” falls apart in the execution.

The Takeaway: Zillow Is Fine for Browsing. It’s Terrible for Building Your Team.

If you get the Zillow itch, here’s the move:

1. Do not tour homes first

2. Run your numbers with a financing professional

3. Get fully pre-approved (ideally underwritten)

4. Choose your agent intentionally

5. Then shop with confidence

Because the team you hire can make this experience:

• smooth and strategic
  or

• an absolute mess

Want Help Building Your 2026 Homebuying Plan?

If you’re thinking about buying this year or next and want to:

• understand what you can actually afford

• build a payment-based strategy

• get a strong approval in place

• be matched with a top buyer’s agent

I’m happy to help you map it out.

👉 The best way to connect is to click here to get started!