Chipped Paint and Character: The Pros and Cons of Buying an Older Home in Boston’s Suburbs

If you’ve been house-hunting around Boston’s charming suburbs—Walpole, West Roxbury, Dedham, or even quaint corners of Wrentham—you’ve probably toured a few older homes. You know the ones: creaky floorboards, ornate trim, and kitchens that whisper, “I haven’t been updated since the Red Sox last won the pennant in 2004.”

But are these historic gems worth the quirks and repairs? Or are you signing up for a never-ending relationship with your contractor?

Let’s talk about what makes buying an older home a romantic dream—or a potential DIY nightmare.

Why Buyers Fall in Love with Older Homes

There’s something about walking into a house with a story. Maybe it’s the solid wood doors, the plaster walls, the crown molding you can’t find in a new build. Older homes in the Boston suburbs were often built with craftsmanship that stands the test of time—and with the kind of materials you just can’t buy at Home Depot today.

The Pros:

• Timeless Character and Charm: Arched doorways, built-ins, wainscoting, original hardwood floors, and quirky little nooks give older homes that unique “soul” newer builds often lack.
• Established Neighborhoods: Think mature trees, sidewalks, neighborhood traditions, and a sense of community that newer developments may not yet offer.
• Solid Bones: Many older homes were built with stronger wood and materials than their modern counterparts.
• Larger Lots: Homes built pre-1980 often have more outdoor space—a huge perk in towns like Norfolk, Westwood, and Wrentham where gardens and patios are lifestyle essentials.
• Investment Potential: A well-located older home with updates? You’ve got equity just waiting to happen.

Why You’ll Want a Good Inspector—and a Bigger Budget

Now for the less dreamy part. Older homes can bring unexpected “surprises,” from outdated wiring to foundation issues. And while not every home is a money pit, some might try their hardest to be.

The Cons:

• Outdated Systems: Old electrical (hello, knob-and-tube), plumbing, or heating systems might need upgrades to meet modern safety standards—or your comfort level.
• Lead Paint & Asbestos Risks: Homes built before 1978 could contain hazardous materials that require professional removal.
• Energy Inefficiency: Drafty windows and minimal insulation could hike up your heating bills—especially during our lovely Nor’easters.
• Costly Renovations: Want an open floor plan? Removing walls in older homes isn’t always simple—or cheap.
• Surprise Repairs: Roofs, chimneys, foundations… oh my. An older home requires regular upkeep, and it’s wise to budget 1–3% of the home’s value each year for maintenance.

What To Look For When Touring an Older Home

Before falling for the vintage wallpaper and clawfoot tub, keep your eyes open (and your inspector’s eyes sharper).

Checklist for Touring an Older Home:

1. Foundation: Look for cracks, uneven floors, or signs of water damage in the basement.
2. Roof Condition: Ask about the age of the roof and gutter system.
3. Windows & Doors: Check for drafts or difficulty opening/closing.
4. Electrical Panel: Make sure it’s updated and properly grounded.
5. Heating System: Ask if it’s oil, gas, or electric and when it was last serviced or replaced.
6. Lead Paint & Asbestos: Consider a professional test, especially if you have young kids.
7. Permit History: If the home had past renovations, were they permitted and inspected?

Should You Buy an Older Home in Walpole or West Roxbury?

It depends. If you’re handy or have renovation experience, the character and value of an older home can be incredibly rewarding. Buyers with a vision (and a cushion in their renovation budget) can turn “outdated” into “Pinterest-worthy.”

But if you’re looking for low-maintenance, move-in ready living? A newer home—or one that’s already been updated—may be a better fit.

Still, some of the most desirable addresses in towns like Dedham, Roslindale, and Westwood are older homes on tree-lined streets with front porches and fireplaces that radiate warmth in more ways than one.

Bottom Line: Embrace the Charm, but Bring a Flashlight (and an Inspector)

Buying an older home in Boston’s suburbs is a lifestyle choice as much as it is a real estate decision. With a little patience and planning, you could find yourself living in a home with more personality than a reality show contestant—and that’s saying something.

Thinking About Buying a Home with Character?

Let’s make sure the charm outweighs the challenges.
Schedule a showing for that house you’ve been eyeing with us today.