5 Types of Houses You Should Never Buy in Boston (No Matter How Good They Look)

Avoid these costly real estate mistakes that trap unsuspecting buyers

Never buy one of these homes in Boston just because it looks like a deal, because deals in disguise are the ones that cost you the most.

The truth is, not every home in this city is a smart buy. Some look cute, some seem like a deal, and some even get hyped as once-in-a-lifetime finds. But behind the scenes? They turn into money pits that are hard to sell and even harder to live in.

Here's the twist: these are the exact homes most buyers chase. They're the ones blowing up your Zillow feed, the ones agents call "hidden gems," and the ones people fight over in bidding wars.

Buy one of these, and you won't just lose money. You'll lose years stuck in a home that drains your finances, your freedom, and your peace of mind.

After nearly ten years helping people buy and sell in Boston, I've seen which homes help families build wealth and which ones turn into nightmares. Today, I'm sharing the five types of homes you should NEVER buy in Boston.

1. The Cheap Condo With Sky-High HOA Fees

Picture this: You're scrolling Zillow and you see a beautiful two-bedroom condo in South End for $650,000. Your heart races because that's $150K to $200K less than everything else you've seen. You think you've found the deal of the century.

Then you see the fine print. HOA fees: $1,200 a month.

That's $14,400 a year. Over ten years? That's $144,000, and that's assuming the fees never go up (which they almost always do).

What's Really Happening

These buildings are usually older, sometimes converted from other uses. The low purchase price exists because the monthly fees are crushing. The building might need a new roof, new elevators, major mechanical updates, and guess who pays for that? You do, through special assessments that can run $10,000, $20,000, or more. In some downtown high-rises, I've seen assessments hit six figures.

I've seen buyers get excited about the low price, only to realize they're paying more monthly than they would for a higher-priced unit with reasonable fees. And when you go to sell? Good luck. Your buyer pool shrinks to people who can afford both the mortgage and that massive monthly fee.

Red flag to watch for: In older buildings without luxury amenities, watch out for fees that feel out of line with the condition of the property. What looks like a deal on paper can turn into a financial trap.

2. The Flip With Lipstick Only

These homes are Instagram-ready. Gorgeous hardwood floors, subway tile backsplashes, stainless steel appliances, fresh paint everywhere. They photograph beautifully, they show beautifully, and they sell fast.

But here's what the pretty pictures don't show you: The electrical system is from 1950. The plumbing is original cast iron that's ready to burst. The heating system is held together with duct tape and prayer.

The Hidden Reality

I've walked through flips where the inspector found knob-and-tube wiring hidden behind new drywall, foundation issues covered by fresh paint, and HVAC systems that looked new but were actually just cleaned up 30-year-old units.

Just last year, I had clients who fell in love with a "fully renovated" Victorian in Dorchester. Beautiful kitchen, stunning bathrooms, everything looked perfect. The inspection revealed $40,000 in immediate electrical work needed and another $25,000 in plumbing issues. The pretty renovation was literally just skin deep.

The problem: These flips are designed to sell fast, not to last. The flipper's goal is maximum profit with minimum investment. They'll spend $15,000 on a kitchen that photographs well, but won't spend $10,000 on electrical work that nobody sees.

My advice: If you're looking at a flip, demand a thorough inspection and budget extra for the systems they didn't touch. Better yet, find a home where the real work has already been done by owners who lived there.

3. The Single-Family With No Parking or Outdoor Space

Boston is tight on space, we all know that. But some houses take "cozy urban living" way too far.

I'm talking about single-family homes where you're circling the block for 20 minutes every night looking for parking. Houses where your "backyard" is a 6-foot concrete slab, and your neighbors can reach out their window and touch your house.

Why This Matters Long-Term

When you're 25 and single, this might seem fine. But life changes. You get a partner who also has a car. You want to host a barbecue. You adopt a dog. You have kids who need space to play. Suddenly, that "cute" cramped house becomes a prison.

And when it comes time to sell, homes with parking and at least some outdoor space consistently move faster and attract stronger offers than similar homes without those features. Your buyer pool is just smaller without them.

Real Example

I had sellers in Charlestown who loved their tiny row house for five years. No parking, no yard, neighbors six inches away. When they went to sell because they needed more space, it sat on the market for months. Every potential buyer loved the inside, then walked outside and said "Where do I park? Where do my kids play?"

Look, I get it. Sometimes no parking or no yard is the trade-off for the neighborhood you want. But understand what you're signing up for. This isn't just about your lifestyle today, it's about your ability to sell tomorrow.

4. The 'Deal' Next to a Major Nuisance

You know these houses. They're the ones priced tens of thousands below market value, and you think "What's the catch?" Well, the catch is permanent.

I'm talking about houses next to Route 93 where you can't have a conversation in your backyard. Houses two blocks from Fenway where drunk crowds walk past your bedroom window at 2 AM every summer night. Houses next to the Orange Line where the walls shake every time a train goes by.

Specific Examples to Watch For

• The "charming" house in the North End that's next to a bar with outdoor seating (sounds fun until you realize their music permit runs until midnight, Thursday through Sunday)
• The "well-priced" condo in Back Bay that overlooks a construction site that won't be done for years
• Properties near major highways, airports, or industrial areas

The Reality Check

You tell yourself you'll get used to it. Maybe the noise won't bother you. Maybe the construction will be done soon. Maybe you'll spend most of your time inside anyway.

But you won't get used to it. And even if you do, the next buyer won't want to try. These nuisances are permanent discounts on your home's value.

Pro tip: If you see a deal that seems too good to be true, drive by at different times of day. Weekend mornings, weekday evenings, Friday nights. Find out why it's priced low, because there's always a reason.

5. The House That's Too Unique

I love character. Boston is full of amazing historic homes with personality. But there's a difference between character and chaos.

I'm talking about the converted church where the living room has 30-foot ceilings and your heating bill is $600 a month. The artist's loft where the only bathroom is accessible by climbing a ladder. The "charming" Victorian where they turned the front parlor into a kitchen, so you have to walk through the dining room to get to the living room.

The Financing Challenge

Truly unusual homes are harder to finance. Lenders get nervous about properties that don't have comparable sales nearby. They may require larger down payments, higher interest rates, or reject the loan entirely.

I worked with buyers last year who fell in love with a converted firehouse in Somerville. Gorgeous space, amazing history, totally unique. But it took us multiple mortgage applications to find a lender willing to finance it, and they ended up paying more in interest because of the risk.

The Resale Reality

When you go to sell, your buyer pool is tiny. Most people want a house with a functional layout, standard bedrooms, and a kitchen that connects to the living area. Plus, unique homes are timing-dependent. They sell when the right person comes along who appreciates the quirks. That could be next month, or it could be next year.

Bottom line: If you're planning to stay for 15+ years and you truly love the uniqueness, go for it. But understand that you're buying for yourself, not for resale value.

What to Buy Instead

Focus on strong fundamentals:

Location: Good location within the neighborhood, not on the busiest street, not backing up to commercial space.

Layout: Functional layout that makes sense. Kitchen connects to living areas, bedrooms are actually bedroom-sized, bathrooms are accessible.

Practical Features: At least one parking space, even if it's just a driveway spot. Some outdoor space, even if it's small. Systems that work (electrical, plumbing, heating), even if they're not brand new.

The Golden Rule

Buy something the next buyer will also want. Not just what you want today, but what a family with two cars and a dog would want. What a young professional couple would want. What empty nesters downsizing would want.

The best investments in Boston real estate are the homes that appeal to the broadest buyer pool. They sell faster, they appreciate more predictably, and they give you options when life changes.

You don't need the perfect house. You need the right house.

Ready to Buy Smart in Boston?

Boston's real estate market doesn't have to be a minefield. With the right guidance, you can find properties that build wealth over time instead of draining your bank account.

If you're serious about buying in Boston and want to avoid six-figure mistakes, I'm here to help. I've guided hundreds of families through Boston's market, and I know which neighborhoods are rising, which ones are peaking, and which properties will actually appreciate versus the ones that just look good on social media.

Don't let a pretty listing photo or a seemingly great deal cloud your judgment. The most expensive mistakes in real estate are the ones that look like bargains upfront.

Your future net worth depends on the decisions you make today. Make sure they're the right ones.