Blog > Homes With a Pool in Hillsborough: Prices, Neighborhoods and Homes for Sale (2026)
Homes With a Pool in Hillsborough: Prices, Neighborhoods and Homes for Sale (2026)
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Looking for homes with a pool in Hillsborough? Of the 231 houses that sold in Hillsborough in the two years to October 27, 2026, 117 (51%) were described in their listings as having a pool; across Silicon Valley it’s 13%. Here’s what they sold for, by size, price and neighborhood, and a one-click search of the ones for sale now.
The short answer
- Median price: $6.5M (all Hillsborough houses: $5.92M), 1% more per square foot than the typical Hillsborough house.
- Typical size: 4,450 sq ft, 5 bedrooms.
- Bidding: 50% sold over asking (all Hillsborough houses: 43%).
- Where they sold most: Hillsborough Park & Hillsborough Knolls (29), Skyfarm & Oaksbridge (21) and Carolands (19).
Shopping now?
- See homes with a pool for sale in Hillsborough now: our Feature Finder reads every live listing’s description and opens on this search.
- Search all homes for sale, then use Save Search to get new listings by email.
- Talk to a Property Nerd about the streets you’re weighing.
By bedrooms
Homes with a pool sold in Hillsborough in the two years, by bedroom count (groups with at least 3 sales).
| Bedrooms | Sales | Median price | Median sq ft |
|---|---|---|---|
| 3 | 4 | $5.28M | 2,425 |
| 4 | 37 | $5.21M | 3,480 |
| 5+ | 76 | $7.55M | 5,100 |
By price
How the 117 sales spread across price bands.
| Sale price | Sales | Share |
|---|---|---|
| under $4M | 6 | 5% |
| $4M to $5M | 14 | 12% |
| $5M to $7.5M | 54 | 46% |
| $7.5M and up | 43 | 37% |
By neighborhood
Our Hillsborough neighborhood guides with at least 3 such sales, placed by map position; “share” is of all house sales in the neighborhood.
| Neighborhood | Sales | Share | Median price |
|---|---|---|---|
| Hillsborough Park & Hillsborough Knolls | 29 | 55% | $6.5M |
| Skyfarm & Oaksbridge | 21 | 43% | $6.25M |
| Carolands | 19 | 54% | $5.9M |
| Ryan Tract, Homeplace & Brewer | 15 | 48% | $9.3M |
| Tobin Clark Estates | 13 | 65% | $6.5M |
| Lakeview & Crystal Springs | 12 | 41% | $5.47M |
Before you buy
- Ask for the pool’s age and equipment, and include it in the inspection; resurfacing and new equipment add up.
- Check the insurance quote early, and the fence and gate rules for pools.
- A pool takes yard space; if you also want an ADU or a garden, look at the lot size, not just the house.
How we counted
Closed sales of houses (MLS property type “single family home”) with a Hillsborough address between October 28, 2024 and October 27, 2026, reported to the MLS and read through the IDX feeds that power our home search, with repeat records from different feeds removed (normalized address plus sale date). A house counts when its listing description says so. Price per square foot uses sales with 400 sq ft or more and is compared with the median for all Hillsborough houses. Neighborhoods are our guides’ outlines, placed by each sale’s map position. Past sales aren’t a forecast or the value of any one home.
Go deeper
Homes with a pool across Silicon Valley, every home type in Hillsborough, Hillsborough neighborhoods compared and the neighborhoods with the most single-story homes, pools and ADUs.
Looking for homes with a pool in Hillsborough?
A Property Nerd will tell you which streets have them, what the recent ones sold for, and set up a search that catches new listings the day they hit. Call (408) 373-1660 or (650) 383-8606, or book a strategy call. Commissions are negotiable, and we offer bundled services, so ask us what’s included.