As the leaves turn gold and the Red Sox pack it in, fall arrives in New England with all its beauty—and unpredictability. We all love a brisk October day and a cider-scented breeze, but as insurance professionals and long-time real estate experts, we also know what’s coming: wind, water, and weather-related claims.
Here at J.M. Whitney, we believe that the best protection starts before the storm hits. Whether you’re a homeowner, a landlord, or a first-time buyer, now is the time to take stock of your property and your coverage.

🏡 Why Fall Is the Smart Season for Policy Checkups
Most folks think about home maintenance in the spring, but autumn is when real damage often occurs. Wet leaves clog gutters, temperatures start to dip, and wind picks up. Small problems—like a loose shingle or low tree branch—can become costly claims.
Beyond physical prep, fall is the ideal time to meet with your insurance broker to review:
- Wind damage and roof coverage
- Tree and landscaping clauses
- Sump pump backups and water damage exclusions
- Liability coverage for icy walkways
- Home office or rental property endorsements
🍁 5 Common Fall Claims (and How to Prevent Them)
- Roof Leaks & Shingle Damage
High winds and rainstorms can dislodge aging shingles. Schedule a roof inspection now to prevent costly leaks later.
- Clogged Gutters & Drainage Backups
Leaves may be pretty, but they wreak havoc on drainage systems. Clean your gutters and downspouts before the next storm.
- Falling Trees & Limbs
Trees near your home? Have them professionally trimmed. You may need to update your policy if a tree falls and causes damage.
- Basement Flooding
Don’t assume your homeowner’s policy covers water backups—many do not. Ask us about sump pump riders or flood insurance.
- Liability from Slips and Falls
As temps drop, early morning frost and wet leaves can create slick spots. Make sure your liability limits are strong, especially if you entertain or rent your property.
💬 Questions to Ask Your Agent
- Do I have enough dwelling coverage based on 2025 construction prices?
- Is my roof age properly documented in my policy?
- Do I have flood or sump pump coverage?
- Should I consider an umbrella policy for broader protection?
- Are my rental or investment properties adequately covered?
These conversations might only take 15 minutes—but they can save you thousands down the road.

🔧 Bonus Tip: Real Estate Market Moves
If you’re thinking of buying or selling before the holidays, know that this is still a strong window in the market. Homes are moving quickly in Watertown, especially 2–3 bedroom condos. Curious about listings? Check out our latest inventory here.
📞 Let’s Check In
Our team has been doing this since 1950. We know what a Massachusetts fall can bring—and we’re ready to help you navigate it. If you haven’t reviewed your policy in over a year, now’s the time.
Call (617) 924-6995 or visit www.jmwhitney.com to schedule a free policy check-up today.
- For any insurance or real estate and commercial management, brokerage, or questions, reach out.
- Featured properties updated regularly: View Our MLS Listings

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