Boston's $4B Housing Problem Is Worse Than You Think

Boston's housing market isn't broken. It's working exactly as designed.

For decades, this city has built world-class hospitals, universities, and biotech companies while refusing to build the housing needed to support the people who make that success possible.

The 4 billion dollar housing shortage isn't a failure. It's the predictable result of a system built to limit growth, protect neighborhoods at all costs, and make scarcity the default. Boston isn't suffering from an affordability crisis. It's suffering from a permission crisis. We don't have a supply problem. We have an approval problem. And the gap between job growth and homebuilding has gotten so extreme that even people making six figures are struggling to stay in the city they work in.

And here's the part no one wants to admit. We can't innovate our way out of this. We can't wait for the market to cool.

The longer Boston keeps its development pipeline this tight, the more the city transforms from a hub for students, young families, and middle-class professionals into a luxury enclave that only the top 10 percent can access.

That shift is happening right now, and the numbers are brutal. I've spent nearly a decade working with buyers, sellers, developers, and families moving in and out of the city. I've watched this crisis unfold street by street, neighborhood by neighborhood, year after year. The pattern is the same everywhere.

So let's break down why Boston's 4 billion dollar housing problem is so much worse than anyone is admitting and what's coming next if nothing changes.

The Jobs-to-Housing Imbalance No One Talks About

Before we get into it, for those that are sticklers for semantics, when I talk about Boston in this video, I am going to include some places in Cambridge and Somerville too. But here is the first place the Boston conversation goes off the rails. People love to debate prices. They almost never look at ratios.

The Math Doesn't Lie

In the last decade:

• Boston added tens of thousands of new jobs in tech, healthcare, life sciences, and education
• But for every job added, we built a fraction of a housing unit
• In some years, it was three, four, even five jobs per one new home
• Neighborhoods like Fenway, Seaport, Cambridge Crossing, Kendall Square, and Longwood saw explosive economic growth without the housing growth to match it

This is not a pricing problem. This is math.

When a city explodes with high-income employment and does not permit enough housing to match, prices do exactly what they're doing now. They explode upward and then they stay there.

If you've ever wondered why someone making $180,000 to $220,000 in Boston feels like they're drowning, this is why. It's not lifestyle inflation. It's structural inflation.

The Cascading Effect

Think about what this actually means on the ground. You have biotech companies hiring hundreds of scientists and researchers. You have hospitals expanding departments and bringing in specialists from around the world. You have tech companies setting up massive offices in Kendall Square and the Seaport. Every single one of those people needs a place to live.

And when you create tens of thousands of high-paying jobs without creating the housing supply to absorb that demand, you don't just see price increases at the top. You see a cascading effect that hits every price tier below it.

The person making $200,000 who would have bought new construction in the Seaport? They're now competing for brownstones in the South End. The person who would have rented in the South End? They're now pushing into Jamaica Plain and Dorchester. The person who would have started in Dorchester? They're getting priced out to Quincy, Malden, or they're leaving Greater Boston entirely.

This is the ripple effect of a jobs-housing imbalance, and it's why the crisis doesn't stay contained to luxury neighborhoods. It flows downward and outward until there's nowhere left to go.

And the tragic part? This was completely predictable. Every city that has gone through this pattern saw the same warning signs. Strong job growth without housing growth always leads to the same outcome. Always. Boston is not special. We just refused to learn from everyone else's mistakes.

Boston's Development Pipeline Is a Funnel, Not a Firehose

Let's talk about the pipeline because this is where the crisis gets real.

Major Projects Aren't Enough

Right now, Boston is delivering a tiny number of large projects compared to the true demand. Think about:

• Seaport
• Cambridge Crossing
• Fenway Center
• Assembly Row
• Suffolk Downs
• Parcel 12
• Boynton Yards
• Nubian Square proposals still crawling through approvals
• Office-to-residential conversion efforts that sound great but are moving very slowly

These sound like big projects. But when you compare them to the needs of a city growing as fast as Boston, it is a drop in the bucket.

Developers will tell you the same thing every time: The land is there. The demand is there. The financing is there. The approvals are not.

Projects take years to get approved. Not months. Years.

The Approval Timeline Problem

And here's what most people don't understand about that timeline. When a project sits in approvals for two, three, four years, costs go up. Interest accrues. Market conditions change. Financing gets more expensive. By the time a project finally gets approved, the pro forma that made sense three years ago no longer works unless you push rents or sale prices even higher.

So developers are forced into a corner. They can only move forward with projects that can absorb those delays and still pencil out financially. And the only projects that can survive that are high-end, luxury developments targeting the top of the market.

If the only homes you allow to move forward are expensive, complex, high-end developments, then the only homes that get built are expensive, complex, high-end homes.

This is not a market failure. This is a policy outcome.

The Vicious Cycle

And the ripple effect hits every single income bracket. When there is not enough housing at the top, high-income renters stay in the middle tier. Middle-income families slide into neighborhoods once considered affordable. Lower-income households get displaced completely.

Scarcity creates competition. Competition creates bidding wars. Bidding wars create resentment and political backlash. Political backlash slows approvals even more.

It's a loop. And Boston is stuck in it.

The irony is that the neighborhoods fighting hardest against new development are the ones that end up changing the most. Because when you block supply, you don't stop demand. You just make the competition more intense. And the people who can pay the most win. Every single time.

The Neighborhood-Level Reality

Let's talk about what this looks like on the ground.

Seaport

The poster child of modern Boston. One of the fastest growing, most expensive, least family-oriented neighborhoods in the state. It was built for jobs and high-income renters. Not for families.

Walk through the Seaport on a weekday and you'll see exactly what I'm talking about. Brand new buildings. Beautiful waterfront. World-class restaurants. And almost no kids. Because the units are small, the prices are astronomical, and the whole neighborhood was designed around attracting young professionals and empty nesters who work in the immediate area.

This is what happens when you build for jobs first and housing second. You get a neighborhood that works for a very specific demographic and prices out everyone else.

South Boston

Once the entry point for young professionals. Now multimillion-dollar townhouse territory with intense competition. New construction is great, but it's not affordable.

I've watched Southie transform over the last decade. Ten years ago, you could still find deals here. You could get into a condo for under $400,000. Now? Those same units are pushing $700,000, $800,000 or more. And the new construction townhouses that everyone wants? You're looking at well over a million, sometimes closer to two.

Jamaica Plain and Roslindale

Loved for their culture and walkability. But appreciation and zoning restrictions keep supply tight. Even condos are climbing out of reach for many first-time buyers.

These neighborhoods have everything people say they want. Great restaurants. Community feel. Green space. Transit access. But because zoning makes it nearly impossible to add meaningful housing supply, the competition is relentless. I see buyers getting outbid on condos that need work. Not luxury units. Condos that need work.

Charlestown

Beautiful. Historic. Tightest inventory in the city. You can go an entire season without more than a handful of listings.

Charlestown is a perfect example of what happens when you combine desirability with extreme supply constraints. It's one of the most sought-after neighborhoods in Boston, and there's just nothing available. When something does hit the market, it's gone in days, usually with multiple offers.

Brighton and Allston

Massive demand from students, young professionals, and institutional investors. Conversions, acquisitions, and renovation cycles continue pushing prices up.

The student demand here is constant. And now you're also seeing young professionals who can't afford Cambridge or Brookline looking at Brighton and Allston as alternatives. Add in institutional investors buying up triple-deckers and converting them, and you've got upward pressure on prices from every direction.

Dorchester

Still one of the last remaining pockets of relative affordability, but even that is changing. Neighborhoods like Savin Hill, Jones Hill, and Ashmont are rising fast because families are realizing it is their last accessible option.

Five years ago, people asked me about Dorchester as a backup plan. Now, it's the first choice for families who want to stay in Boston but can't afford anywhere else. And because demand is surging while supply stays limited, appreciation is accelerating. The neighborhoods that used to be affordable are becoming expensive. And there's nowhere left below them.

This is the story everywhere. Demand climbs. Supply trickles in. Neighborhoods shift a full price tier in 12 to 36 months.

Why Even "Cooling" Markets Stay Expensive

People ask me all the time: "Is Boston finally going to correct?" "Are prices going to drop?"

Here is the truth: Even if rates fall, prices won't collapse. Even if rates rise, prices won't collapse.

Because Boston does not have a cyclical pricing problem. It has a structural supply constraint.

Think Manhattan, San Francisco, or DC

Think of Boston the same way you think about Manhattan, San Francisco, or DC. Cities where economic opportunity far outweighs the ability or willingness to build.

In most markets, when prices get too high, developers build more supply and prices eventually stabilize or correct. That's how functioning housing markets work. But in Boston, the supply response is so constrained by policy that even when demand slows down temporarily, there's not enough inventory to create any meaningful price relief.

What Keeps Prices High

Here's what keeps prices high even during slower seasons:

Zoning that limits multifamily construction. You've got neighborhoods with excellent transit access that are zoned exclusively for single-family homes. That's not an accident. That's policy.

Neighborhood groups that block density even where transit access is excellent. Every new project, no matter how well-designed or how much the city needs it, faces years of opposition and delays.

A long permitting timeline that kills smaller projects financially. Small and mid-sized developers can't absorb three or four years of carrying costs. So they either don't build, or they sell to larger developers who can. And larger developers only build luxury because that's what survives the timeline.

A shortage of starter homes within the city. First-time buyers are competing for a tiny pool of inventory, which keeps those entry-level prices elevated even when the high end softens.

Institutional investors entering middle-tier neighborhoods. As investors get priced out of premium areas, they move into traditionally middle-class neighborhoods, bringing cash offers and driving up prices further.

The Fundamentals Don't Change

Boston has one of the strongest, most diversified job markets in the country. When that job market expands without expanding housing, you get exactly what we have now: high prices, low inventory, permanent competition.

And here's the part that surprises people. Even when interest rates rise and buyer demand softens, inventory stays low. Because sellers don't have anywhere to go either. They're locked into low rates. They can't find their next home. So they stay put. And that keeps inventory tight, which keeps prices elevated, even in a cooling market.

This isn't a market that corrects like Phoenix or Vegas. This is a market that stays expensive because the fundamentals never change.

What Happens Next If Nothing Changes

If nothing changes, Boston becomes something very different from what people imagine it to be.

Here is the trajectory:

Entry-level inventory nearly disappears except for condos in older buildings. And even those condos become increasingly expensive as competition intensifies. First-time buyers find themselves competing with investors, downsizers, and people who would have bought single-family homes if any were available.

Neighborhoods that were affordable five years ago become premium neighborhoods. We're already seeing this happen. Areas that were considered starter neighborhoods are now priced like established, desirable markets. And that shift happens faster than most people expect.

The middle class shrinks inside the city and relocates to suburbs and exurbs. Teachers, nurses, city workers, small business owners. The people who make the city function but don't earn tech or biotech salaries. They're being pushed further and further out.

Commutes get worse because the workforce no longer lives near job centers. When your employees can't afford to live anywhere near where they work, they're commuting from Brockton, Worcester, or Southern New Hampshire. That affects productivity, quality of life, and the city's ability to attract and retain talent.

Developers only build luxury because those are the only projects that survive the approval bottleneck. The projects that pencil out are the ones targeting the absolute top of the market. Everything else gets killed by the timeline, the costs, or the opposition.

Families stop considering Boston at all because the math simply doesn't work. I've had this conversation dozens of times. Families who love the city, who want to stay, who have roots here. And they run the numbers and realize they'd have to sacrifice everything else in their budget just to afford housing. So they leave.

Who Is Boston For?

And people ask: "So who is Boston for?"

Right now, the answer is: people who earn a lot, or people who bought early.

If you bought ten years ago, you're fine. You're sitting on massive appreciation and your monthly payment is manageable. If you're making $300,000 or more, you can still make it work, even if it's painful.

But if you're middle-class and trying to enter the market now? If you're a young family earning a good living but not an exceptional one? The city is pricing you out. Not slowly. Quickly.

That is the danger of a permission-based housing system. Scarcity is not an accident. It becomes the culture. And once scarcity becomes the default, the city stops working for the majority of people who want to live there.

Navigating Boston's Housing Market

If you are relocating to Boston, thinking about moving within the city, or trying to find the right neighborhood at the right price point, my team and I do this every single day. We help you find the pockets of value and make smart moves based on where the city is going, not just where it is today.

If you are thinking about moving to Boston or trying to figure out which neighborhoods still offer the best value, I put together a free relocation guide that breaks down schools, commutes, lifestyle fit, pricing, and what you need to know before you even start touring homes.

This guide covers everything from transit access to school ratings to which neighborhoods are seeing the fastest appreciation to where first-time buyers are still finding opportunities. It's the same information I walk clients through before we even start looking at properties, because knowing the landscape before you start searching saves you months of frustration and helps you avoid expensive mistakes.

We work with people in your exact situation all the time. People who are trying to navigate a market that doesn't make sense on paper. People who need to understand which neighborhoods still offer opportunity, which ones are overheated, and where the next wave of appreciation is likely to happen.

We help you think through commutes, schools, resale potential, and lifestyle fit. We help you avoid the neighborhoods that look good on Zillow but don't match your actual needs. And we help you move quickly and strategically when the right opportunity shows up, because in this market, hesitation costs you.

Use the link below to schedule a time to talk with us. We will walk you through neighborhoods, commutes, schools, and the strategies that actually work in this market. No pressure, no sales pitch. Just honest guidance from people who do this every single day and know this market inside and out.

And if you want to go deeper into what it's actually like to live in Boston, check out my guide on the top 10 questions about living in Boston, which breaks down lifestyle fit, costs, commute realities, and everything people ask me before they move here. It'll give you a much clearer picture of whether Boston is the right fit for you and what you need to know before you make the move.