Written by Erik Windrow
There’s a relatively new word gaining attention in the technology world: enshitification.
Coined by technology writer Cory Doctorow, the term describes what can happen when an online platform starts by creating an exceptional experience for its users, then gradually shifts its priorities toward maximizing revenue from advertisers, vendors, and businesses.
The result?
The platform may still look convenient. It may still appear helpful. But the experience can become increasingly designed around the people paying for access, rather than the consumer using the service.
If you’ve ever searched online for a contractor, insurance company, mortgage lender, or real estate agent and wondered whether the “top” result was actually the best option, or simply the one with the biggest marketing budget, you’ve encountered a version of this problem.
Real estate is no exception.
Many buyers assume that when they click “Contact Agent” on a large national real estate website, they’re automatically being connected with the listing agent or the most qualified local real estate professional.
That isn’t necessarily the case.
Depending on the platform and its business model, an inquiry may be routed to an agent participating in a paid advertising or lead generation program. That agent may be an excellent professional. However, the reason you were connected with that person may have more to do with their participation in the platform’s marketing program than with an independent evaluation of their experience, local knowledge, or transaction history.
Similar models exist across many industries, including mortgage lending, insurance, home services, moving companies, and other professional services.
There’s nothing inherently wrong with advertising. Real estate professionals have promoted their businesses for generations through newspapers, magazines, television, radio, websites, and social media.
The important question for consumers is simply:
Why am I being connected with this person?
Is it because they are the best fit for my needs?
Or because they paid for the opportunity?
Those can be two very different things.
Buying a home isn’t like ordering a phone charger online.
A home may be one of the largest financial investments a person or family ever makes. The decisions made during the process can affect finances, lifestyle, and long-term plans for years.
That’s why choosing representation based solely on who appears first in a search result, or who responds to an online inquiry the fastest, can be shortsighted.
Experience matters.
Negotiation matters.
Market knowledge matters.
Communication matters.
Relationships matter.
And perhaps most importantly, having someone who understands your specific goals matters.
The right real estate professional should do more than open doors and send listings. They should help you understand the market, identify potential issues, negotiate strategically, and guide you through the decisions that come with buying or selling a property.
Consumers often don’t realize how online real estate lead generation can work.
While every platform has its own business model, a simplified version can look something like this:
A consumer visits a national real estate website.
They search for properties or local professionals.
They click “Request Information” or “Contact an Agent.”
Their inquiry may be distributed to participating agents.
Those agents may pay the platform for advertising, leads, or other marketing opportunities.
Again, advertising itself isn't the problem.
The issue is transparency.
Consumers deserve to understand whether a recommendation is based on qualifications and fit, or whether the recommendation is influenced by who paid for the opportunity.
That distinction becomes especially important when the service involves one of the biggest financial decisions of your life.
Large national real estate websites have brought tremendous convenience to consumers.
Searching for homes is easier than ever. Buyers can browse properties from their phones, compare prices, view photos, research neighborhoods, and receive updates almost instantly.
That technology is valuable.
But technology has limitations.
An algorithm can identify homes that match your search criteria.
It can't replace someone who knows the community.
It doesn't attend local meetings.
It doesn't negotiate inspection repairs.
It doesn't walk a property and notice something that doesn't appear in the listing photos.
It doesn't know how a particular neighborhood responds to changing market conditions.
It doesn't have relationships with local professionals.
And it doesn't understand the nuances that can matter when you're buying or selling along the Delmarva coast.
Local knowledge still matters.
Instead of simply asking:
“How quickly did they respond?”
Consider asking better questions:
How much experience do you have in the market where I want to buy?
How frequently do you work in this specific community?
How do you communicate with clients?
What is your strategy when multiple offers are involved?
How do you help buyers evaluate inspections, insurance, HOA considerations, and other potential issues?
How familiar are you with waterfront and coastal properties?
Who will personally guide me through the transaction?
What happens after I make an offer?
The answers to those questions may tell you far more about whether an agent is right for you than their position on a webpage.
Buyers aren't the only ones navigating an increasingly automated real estate world.
Sellers are surrounded by online estimates, instant valuations, automated marketing systems, and promises of immediate offers.
These tools can be useful.
But an online valuation is still an estimate.
While technology can analyze enormous amounts of data, it doesn't necessarily understand every factor that can influence the value and marketability of a specific property.
Two homes with similar square footage can have dramatically different values because of location, condition, views, improvements, lot characteristics, amenities, community restrictions, or buyer demand.
This becomes particularly important with coastal and waterfront properties, where seemingly small differences can have a significant impact.
The fastest advice isn't always the best advice.
And the highest automated estimate isn't necessarily the most realistic strategy.
The internet has made finding homes easier.
Finding the right professional still requires a little homework.
Read reviews.
Ask people you trust for recommendations.
Interview more than one agent.
Look at experience.
Ask questions.
Pay attention to how they communicate.
And don't be afraid to ask how they generate their business and how they were connected with you.
Choose someone because they are the right fit for your situation, not simply because an algorithm introduced you.
At The Windrow Group, we believe real estate should remain personal.
Technology is an incredible tool. We use it every day to help our clients search, communicate, analyze information, market properties, and navigate an increasingly complex real estate environment.
But technology should support the relationship, not replace it.
We believe buyers and sellers deserve to know whom they are working with, why that professional is being recommended, and what experience they bring to the table.
Whether you're buying your first home, selling a waterfront property, investing along the Delmarva coast, or relocating to the beach, our goal is simple:
Provide honest guidance, local expertise, and representation that puts your interests first.
Because in a world increasingly driven by algorithms, automation, and paid recommendations, genuine relationships still matter.
And when you're making one of the biggest financial decisions of your life, whom you trust to guide you matters even more.
Published: September 08, 2026