Fall Home Prep Checklist for Greater Boston Homeowners

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Greater Boston home inspection showing roof, chimney, gutters, windows, and heating system.October in eastern Massachusetts has a way of arriving in a hurry.

One week you’re watching leaves turn on the drive through Sharon. The next week you’re scraping frost off the windshield and realizing you never got around to calling the HVAC company. That gap — the weeks between Labor Day and Columbus Day — is the most valuable maintenance window you’ll have all year. Use it right and you head into winter ahead. Miss it and you’re making reactive phone calls in the cold.

Here is exactly how to use it.

Is Your Heating System Actually Ready To Run?**

The single most important thing you can do in September is confirm your primary heat source is ready before the first hard cold snap.

That sounds obvious. It almost never gets done on time.

For homes on oil heat — and there are a lot of them in the South Shore and MetroWest corridor — September is the right moment to schedule an annual oil burner tune-up. A qualified technician cleans the nozzle, checks the heat exchanger, inspects the flue pipe, and tests safety controls. A burner that failed quietly over the summer doesn’t announce itself until you turn the thermostat up on a 28-degree night. That is not the moment you want to find out.

Gas furnaces and boilers need the same attention. Check the burner flame color (steady blue is good; yellow or orange wavering means call someone), verify that the condensate drain line on high-efficiency units is clear, and replace the filter if you haven’t done so in the last few months. A dirty filter is the single most common reason a system underperforms all winter.

Heat pumps — increasingly common in newer and recently renovated greater Boston homes — need the outdoor unit cleared of debris and coils cleaned before the heating season starts. They are efficient when running clean. They are expensive when they are not.

Does Your Chimney Need Attention Before Fireplace Season?

If there is a fireplace or wood stove in your home, yes — it does.

The National Fire Protection Association recommends an annual chimney inspection for any fireplace in use. In greater Boston’s older housing stock, many chimneys have never been looked at since the house was built. Creosote buildup, deteriorated mortar, cracked flue tiles — none of these are visible from the living room. A certified chimney sweep does a Level 1 inspection in under an hour. That one hour is the difference between a cozy fire and a chimney fire in January.

If the fireplace is decorative and never lit, you can skip the sweep — but check the damper anyway. A stuck-open damper is a direct pipeline for cold New England air straight into your living room all winter.

What Is The Basement Telling You In September?

Fall rains in eastern Massachusetts are significant. Before the heavy precipitation cycles of October and November arrive, spend 15 minutes in your basement.

Look at the base of every exterior wall. Look at the floor near the sump pump pit. Look at the area beneath windows. Any white powdery mineral deposits on concrete or block — called efflorescence — tell you water has been migrating through the wall. Staining at floor level means the same. These are not cosmetic issues. They are symptoms.

If your sump pump has a backup battery, test it now. The backup exists for the exact scenario where you need it most: a power outage during a nor’easter when the pump should be running hardest. September is the time to find out whether it works — not during the storm.

If you see active standing water, soft drywall, or visible mold at any point during this walk-through, do not ignore it. A damp Massachusetts basement in October becomes a serious problem by December.

Fall home inspection showing roof, chimney, gutters, windows, and basement systems.Is Your Building Envelope Sealed For Winter?

Cold air finds the smallest gaps, and greater Boston winters are long.

Walk the perimeter of your home and check the caulking at every point where two different materials meet: window frames against siding, door frames against brick or sheathing, where pipes or utility lines enter the house. Caulking that was applied five years ago has likely cracked and pulled away in places. A tube of paintable exterior caulk and one afternoon of careful application will measurably reduce your heating bills.

Weatherstripping on entry doors is worth checking every fall. Close each exterior door and look for daylight around the frame. Press the door closed firmly — if there is noticeable give before it stops, the seal is not adequate. Compression-style door sweeps and foam weatherstripping are inexpensive and straightforward to replace.

Have You Cleared The Gutters Before Leaf Fall?

One of the more common calls homeowners receive from inspectors — whether at the time of sale or during a maintenance check — is about clogged gutters directing water against the foundation or into the fascia.

In greater Boston, peak leaf fall runs October into early November. Scheduling a gutter cleaning before the leaves are fully down is counterproductive — do it too early and you’ll need to do it again. But scheduling it for mid-October keeps you ahead of the freeze. Water trapped behind a leaf dam in a gutter that freezes is the beginning of ice dam damage. That is a repair category nobody wants to enter.

The Bottom Line For Greater Boston Homeowners

None of this is complicated. All of it is time-sensitive. The September window in New England is real — heating companies are still scheduling non-emergency appointments, contractors are still available, and you are not working in the cold.

If you want a professional set of eyes on your home before the season changes — heating, basement, envelope, and everything in between — a maintenance inspection from Tod Whiting and Missy Boyle gives you a documented picture of exactly where you stand.

Schedule a maintenance inspection or call Tod Whiting directly at (781) 828-1972 or https://metrobostonpropertyinspections.com/ today!

Do it in September. October has a way of arriving before you’re ready. 

Andrea Gramolini

ASSOCIATE INSPECTOR

My name is Andrea, and I am the newest Associate Home Inspector at Metro Boston Property Inspections. I joined the team in May of 2023 and am learning quickly with such an experienced and dedicated team.

Before coming to Metro Boston Property Inspections, I worked in construction for over 7 years. I enjoy helping others with the process of purchasing their home or commercial property, as real estate is typically the largest investment of someone’s life. Knowing I am adding value to others’ experiences in the real estate purchasing process is very rewarding.

I look forward to working with you when the time is right for your first or next property.

Kristopher Crowell

ASSOCIATE INSPECTOR

My name is Kristopher. My attention-to-detail and fascination with building & materials science are well-suited to this work. I joined Metro Boston Property Inspections in October 2022.

I’ve spent the last 12 years as a project manager on hundreds of residential and commercial projects. Understanding the need for quality installation, maintenance, and repair, I provide unique insights into ensuring the systems we depend on function and last as we intend them to.

Buying a home is a pivotal moment for most people, and my role with MBPI is to help you navigate those crucial days. 

Mark Weinzierl

Licensed Home Inspector

My name is Mark, I am married and have 1 son! Previous to becoming a home inspector, I was a science and engineering teacher and later a property manager.

I joined the team at Metro Boston Property Inspections in 2021. It has been a great experience working with and learning from the many professionals here at MBPI.

For many, buying a home is the biggest financial decision they have ever made. As a licensed home inspector, I get to help people during this exciting and stressful process by teaching them about the homes they are hoping to buy.

I look forward to meeting you when the time comes to for you to purchase your first, or next home!

Robert Madzar

Residential Construction Home Inspector

My name is Rob Madzar I joined the Metro Boston Property Inspection team in 2019 after 30 years of working in residential construction.


  • In addition to my home inspector license, I have a construction supervisor’s license and a real estate agent’s license.
  • I am mold certified
  • I was looking to join an established inspection company with a proven track record of excellent Customer service, and high expectations of their employee’s professionalism. I found both at Metro Boston Property Inspections.
  • I look forward to helping show clients our high standards.



We provide real estate inspections for both residential and commercial clients ranging in size from small garden-style apartments up to 100,000 SF commercial properties. We provide our clients a computer-generated narrative report within 24 hours of the inspection for residential clients, and depending on the size, style and condition of the property, commercial reports may take up to 5 days.

Missy Boyle

Operations Manager

Hello, my name is Missy and I am the Operations Manager. I have been with MBPI since June of 2017. I came to MBPI with an extensive real estate background. I worked as a licensed real estate assistant for over 12 years at one of the largest real estate companies in the world.

I love helping clients and agents alike by educating them on our services and doing whatever I can to accommodate their busy schedules! I consider it a personal challenge to exceed everyone’s requests. I love talking with people and can relate to them and what they are going through because of my real estate background. I also love when it’s time to follow up with our clients and agents after the inspection…it is so wonderful to hear all the kind things they have to say about our inspectors and how thorough and wonderful they are!

Customer Service is a HUGE priority for all of us at Metro Boston Property Inspections, and we can’t wait to help you when you’re ready for us!

Tod Whiting

CEO and President

Hello, I am pleased to introduce myself to our past and future clients. I am a Massachusetts Licensed Home inspector, Certified Radon Measurement Technician, Certified Mold Inspector, Registered pest Inspector, and Certified Commercial Inspector.

Prior to the creation of MBPI, I was a franchisee with Allstate Home Inspection & Household Environmental Testing, 1998 to 2007. As a member of AHI, I was hired by corporate to provide training to new franchisees.
Training and coaching are passions of mine and I enjoy developing new inspectors in order to create the most consistent inspection experience there is.

I am a member of the International Association of Certified Home Inspectors (InterNACHI), Indoor Air Quality Association, and the Association of Radon Scientists and Technologists. I am an affiliate member of the Asian Real Estate Association of America.

For 22 years I coached competitive fastpitch softball from kindergarten instructional leagues to college showcase teams. I still play softball today on a co-ed team with my daughters.

My real passion is running my business and creating opportunities for our team, our clients and our referral partners to realize their dream life and to develop opportunities to make a real difference in our community and the world.