Buying a home in the South Shore or Greater Boston is one of the biggest financial and lifestyle decisions you’ll ever make. And while it’s exciting, it can also be overwhelming — especially in a competitive market where the right home may attract multiple buyers.
Here’s the truth: even with all the planning in the world, many buyers experience at least one regret after closing. A 2024 Clever Real Estate survey found that 82% of recent homebuyers admitted they wished they’d done something differently.
At The Jenkins Group, our goal is to help you avoid those “what if” moments by guiding you through the process, keeping your priorities front and center, and spotting the red flags you might miss. To get started, here are 15 key questions that can help you buy with confidence.
1. Can I Afford This Home?
Too often, buyers start by falling in love with a home before getting preapproved for a mortgage. In Greater Boston, where home prices can move fast, that’s a recipe for heartbreak. A preapproval not only gives you a realistic budget but also strengthens your offer in a competitive market.
2. What Kind of Expert Can Help Me?
Buying in the South Shore or Boston neighborhoods means navigating bidding wars, older housing stock, and complex negotiations. The right real estate team (hi, that’s us 👋) will not only help you evaluate properties, but also connect you with trusted lenders, inspectors, and contractors.
3. Am I Looking Past Finishes and Features?
That sparkling new kitchen in Hingham or the trendy paint job in Dorchester might be tempting, but don’t let it blind you to the big-ticket items: roof, foundation, HVAC, electrical. Cosmetic upgrades are replaceable — structural issues are not.
4. Can I Keep Up With Maintenance?
Historic homes in Quincy, colonials in Milton, or seaside properties in Hull all come with upkeep. Plan to spend 1–4% of the home’s value on annual maintenance. Don’t forget snow removal in winter and coastal wear-and-tear near the ocean.
5. Am I Accounting for Extra Costs?
Beyond your down payment, closing costs, property taxes, and insurance, Greater Boston buyers may also face HOA dues, flood insurance (for coastal towns), or high utility bills in older homes. Always build in a buffer.
6. How Old Are the Home’s Systems?
In many South Shore towns, homes are 50+ years old. That charm comes with aging systems. Always ask about the age and condition of the roof, heating system, windows, and water heater.
7. Sniff Out Potential Problems
Musty smells in a basement could mean moisture issues (common in New England homes). A “fishy” odor could signal electrical issues. Trust your senses and investigate further.
8. How Is the Home Oriented to the Sun?
Natural light matters, especially during long New England winters. South-facing homes in Weymouth or Braintree may be warmer and brighter, while shaded homes could mean higher heating costs.
9. Is There Enough Space?
Don’t just look at square footage. Can you park two cars in the driveway during a snowstorm? Will your furniture fit in those charming older rooms with tighter dimensions? Think about function, not just numbers.
10. How Is the Neighborhood?
Drive the commute during rush hour. Check walkability to schools, shops, or the Red Line. Visit at night and on weekends. South Shore towns can vary street by street — we’ll help you figure out if the vibe matches your lifestyle.
11. Will This Home Work in the Future?
Planning to grow your family? Need a home office? Whether you’re buying in Boston’s city condos or a Hanover colonial, make sure the home will fit your lifestyle for years to come.
12. Is the Asking Price Fair?
We’ll run a Comparative Market Analysis (CMA) to ensure the home’s price reflects recent sales, condition, and neighborhood trends. In today’s market, the right price strategy can make or break your offer.
13. What Do the Seller Disclosures Reveal?
Massachusetts law requires sellers to disclose certain issues, but some things aren’t always obvious. Pay close attention to signs of water damage, foundation cracks, and environmental concerns like radon.
14. What Does the Home Inspection Report Say?
Inspections in New England homes often reveal long lists of small issues. Focus on the big ones: roof, foundation, electrical, plumbing. If a house has deal-breaking issues, we’ll guide you on when to negotiate and when to walk away.
15. Are the Big-Ticket Items in Good Shape?
Replacing a roof, HVAC, or windows can cost tens of thousands. Always prioritize these in your decision-making.
Bottom Line: Buy Smart, Not Just Fast
In the fast-paced South Shore and Greater Boston market, it’s easy to get caught up in emotions or competition. But if you ask the right questions and focus on what truly matters, you’ll avoid regrets and land in a home you love for the long haul.
The Jenkins Group is here to guide you every step of the way — from financing to inspections to closing day. Whether you’re buying your first Quincy condo or upgrading to your forever home in Hingham, we’ll make sure you feel confident in your decision.
