Before the first rain hits the Peninsula, six things deserve attention on homes in Atherton, Palo Alto, Menlo Park, Los Altos, Los Altos Hills, Woodside, and Portola Valley: gutters and roof, drainage and grading, the furnace or heat pump, window and door seals, mature trees, and the vendor calls you make now instead of in December. Around this time every year, our team gets the same calls, and nearly all of them are about damage that could have been caught before the first storm. In the video above, I walk through my own home and show exactly what we tell clients.
Check | When | Why it matters here |
Gutters and roof | Before first rain | A full dry season of debris turns one clogged gutter into fascia and foundation damage in a December storm |
Drainage and grading | Before the wet season | On older Peninsula lots, grading often never kept up with decades of landscaping changes; pooling at the foundation is the warning sign |
Furnace or heat pump | Early fall | A preseason inspection costs far less than an emergency call over the holidays, when every technician on the Peninsula is booked |
Window and door seals | Fall | Original wood windows in older homes here need recaulking and weatherstripping more often than owners expect |
Mature trees | Now, before storms | Significant canopy is standard on these properties, and the first big winter storm is when weak limbs come down |
Why does fall maintenance matter more on the Peninsula?
Because our summers are dry. Debris builds up on roofs and in gutters for months without rain to reveal the problem; systems like furnaces sit unused for half the year, and the first real storm tests everything at once. Homes here also skew older and more heavily treed than most of the Bay Area, which concentrates exactly the risks on the list above.
What should I check first?
Start at the top. Have gutters cleared and the roof inspected for loose or cracked material before the rain starts. A clogged gutter in a heavy December storm does not stay a gutter problem; it becomes a fascia problem and sometimes a foundation problem.
How do I know if my drainage is a problem?
Walk your property line and look at where water actually goes when it rains. On many of the older properties we work with, the grading was never updated as landscaping changed over the decades. If water pools near the foundation instead of draining away, address it before the wet season, not after.
What about heating, windows, and trees?
If the furnace or heat pump hasn't run since last winter, don't wait for the first cold night to find out whether it needs service. Check the seals and weatherstripping on windows and exterior doors, especially original wood windows, which are beautiful and higher maintenance. If your trees haven't been looked at by an arborist this year, now is the time, because the first big storm finds the weak limbs for you.
Does maintenance like this affect resale value?
Directly. Deferred maintenance is one of the first things buyers and inspectors flag in this market, and the highest-return prep for selling is usually this kind of care, plus paint, flooring, and staging, rather than a major renovation. A home that has clearly been maintained earns trust before negotiations start.
Frequently asked questions
When should I winterize my home in the Bay Area?
Before the first sustained rain, which typically means completing gutter, roof, drainage, and tree work by late October or early November.
What is the most common winter damage on Peninsula homes?
Water intrusion that starts at clogged gutters or poor grading, followed by limb damage from unmaintained mature trees during the first major storm.
Do you share your vendor list?
Yes. We maintain relationships with arborists, inspectors, and contractors across the Stanford area communities, and we share recommendations with clients and neighbors on request.
Need a trusted arborist, inspector, or contractor on the Peninsula? Reach out to us and we are happy to share some recommendations.
Happy autumn!