Hillsborough
Hillsborough real estate is defined by what the town leaves out. There is no commercial downtown, no shopping district and almost no housing other than single-family homes on large lots. The town sits about 17 miles south of San Francisco, bordered by Burlingame, San Mateo and Interstate 280. Its terrain is hilly and winding, with steep slopes on the western side that flatten toward El Camino Real, and three creeks drain the wooded hillsides.
Buyers here are usually weighing land, setting and architecture rather than walkability. Properties run from mid-century houses on lots of roughly half an acre to large estates with gardens, pools and guest houses, and the town’s zoning and design rules shape what can be built or changed. Dining, groceries and shops are in neighboring Burlingame and San Mateo, and this guide labels those places as such. We cover the layout, the housing types and what we plan to check with you before an offer.
About Hillsborough
Residents voted to incorporate Hillsborough as a town in 1910. It grew out of the Rancho San Mateo land grant, and early owners built country houses in the hills west of the rail line. Notable properties include Carolands, a French-style château listed on the National Register of Historic Places, and houses by architects including Willis Polk, Julia Morgan, Frank Lloyd Wright and Richard Neutra. Non-residential land includes parks, a golf course, a country club and civic buildings, and there is no commercial zoning. Next door, Burlingame real estate has the nearest shopping streets.
The town runs its own town hall and police department on Floribunda Avenue and a recreation department on Ralston Avenue. There is no BART or Caltrain station in Hillsborough. The nearest Caltrain stops are in Burlingame and San Mateo, and BART is a short drive north at the Millbrae station in Millbrae. El Camino Real marks the eastern edge and Interstate 280 runs along the west, so most trips begin by car. Streets are narrow and curving, and some properties sit behind mature hedges and gates.
Residential Overview
Property Types
Single-family homes on large lots make up essentially all of the housing.
Estate architecture
Mediterranean and Spanish Colonial Revival estates, Tudor and Georgian houses, French-inspired chateaux, Colonial Revival homes and mid-century modern designs.
What zoning allows
Zoning has historically required large lots and a minimum house size, and condominiums, townhomes and apartments are essentially absent.
Accessory dwelling units
State accessory-dwelling-unit rules may permit guest units.
Ownership and private roads
Ownership is usually fee-simple, and some parcels sit on private roads with shared maintenance agreements, which are worth confirming early.
Market Trends
Hillsborough has relatively few sales in a typical year, so the market is thin and individual listings matter more than trends. Homes in good condition and priced to their land and setting can draw strong interest, while properties priced well above comparable sales may sit for months. Because so few homes trade in a given year, a single unusual sale moves the figures more here than in a larger market. Several items deserve early attention: wildfire hazard maps for western parcels near wooded greenbelts, hillside and drainage conditions, and the Town's review requirements for remodels and new construction. For wider context, see our Bay Area real estate guide.
Price Range
(Rolling 12-month average, not a valuation for any one home. Updated November 2026.)
Median price per square foot:
$1,711
Hillsborough is typically among the highest-priced communities on the Peninsula, and value is driven largely by land: parcel size, setting, views, and the age and quality of the structure. Some buyers purchase mainly for the lot and plan to rebuild, while others look for updated homes ready to occupy. Flatter parcels near El Camino Real price differently from hillside properties with views, and gated or private-road settings add another layer.
Median sale price:
$6,525,000
Because each property is so individual, comparable sales are sparse and a price per square foot says little. We read lot, permit history and architectural quality closely, and the data suggests that careful comparison matters more here than any average.
Time from listing to closing:
34 days
Measured from the listing date to the recorded sale, so it includes the escrow period and runs longer than a days-on-market figure.
Sources. Sale price, price per square foot and time from listing to closing: our analysis of county records and MLS data via Realist, sales from October 2025 to September 2026, all property types, Hillsborough city limits. No city-level rent figure is published for this market, so the rent line is omitted. Figures move month to month; ask us for the current read on a specific block or price band.
Data covers the twelve months ending September 2026 and is subject to change. Last updated November 2026.
Want today's exact numbers, including active listings and recent sales?
Community and Neighborhood Life
Carolands Chateau
Recreational and Educational Programs
Free, curator-led tours of the château and gardens at 565 Remillard Drive run on Wednesday afternoons by advance reservation, with dates released a month or two ahead.
Hillsborough Recreation Department
Recreational and Educational Programs
Based at 2600 Ralston Avenue, the department offers children’s classes, summer and sports programs and enrichment courses at sites around town.
Hillsborough Town Hall public meetings
Volunteerism and Civic Engagement
The Town’s public meetings at 1600 Floribunda Avenue are where residents can weigh in on design review, roads and town services.
Burlingame Fresh Market
Support for Local Businesses and Markets
Because Hillsborough has no commercial district, the nearest weekly market is this Sunday market on Park Road in neighboring Burlingame.
Central County Fire Department CERT
Emergency Preparedness and Safety Programs
The department’s free CERT basic training is held in neighboring Burlingame, with a fall 2026 course that ran September 29 to October 20.
Downtown Burlingame Fall Fest Block Party
Local Events and Festivals
In neighboring Burlingame, downtown businesses hold a free block party on Howard Avenue, listed for October 25, 2026.
Our Favorite Spots
Parks and Recreation
Vista Park
at 1030 Vista Road is a long, narrow neighborhood park in Hillsborough with a large play field, climbing rocks and play equipment for kids, an arbor and picnic tables.
Crossroads Park
at Black Mountain Road and Hayne Road, also in Hillsborough, is a small green space on the site of an abandoned water tank, with benches and a drinking fountain for a quiet pause along the road.
Washington Park
at 850 Burlingame Avenue is just over the line in Burlingame, an 18.9-acre park with a playground, picnic area, four tennis courts and four pickleball courts, with lights available.
Ray Park
at 1525 Balboa Way is also in Burlingame, on the Hillsborough side of that city, a 5.9-acre park with a playground, tennis, basketball, baseball facilities and picnic areas.
Shopping and Dining
Copenhagen Bakery & Cafe
at 1216 Burlingame Avenue, in neighboring Burlingame, has baked Danish pastries since 1977 and lists the Princess Cake among its specialty cakes; the bakery opens at 6 a.m. daily, with breakfast and lunch from 7 a.m.
Morning Glory
at 1436 Burlingame Avenue, in neighboring Burlingame, is a women's clothing boutique founded in 1972 by two sisters, with an eclectic, fashion-forward mix of clothing and accessories.
Himali Bistro
at 1251 Broadway, in neighboring Burlingame, serves Nepali and Indian dishes in a small dining room; try the steamed momos over achar sauce, the tandoori lamb kebabs or a mango lassi.
Fiero Caffe
at 106 S El Camino Real is also in San Mateo and serves espresso, pasta and breakfast.
Health and Wellness
Sutter Mills-Peninsula Medical Center, Burlingame Campus
at 1501 Trousdale Drive is a full hospital in neighboring Burlingame offering emergency and surgical care, heart and vascular care, childbirth services and a Mobile Stroke Unit.
Peninsula Health Care District Health & Fitness Center
at 1875 Trousdale Drive, in neighboring Burlingame, is a gym whose class list reaches past the usual, with balance classes, chair yoga, tai chi, Pilates and Zumba alongside the equipment floor.
MNTSTUDIO Burlingame
at 1465 Burlingame Avenue, in neighboring Burlingame, is a reformer Pilates studio offering reformer classes and private sessions, and it also runs reformer and heated mat certification programs and teacher trainings.
Little House Pilates
at 450 Turner Terrace is a small Pilates studio in San Mateo, near Hillsborough's southern edge.
Neighborhood Map
Hillsborough Real Estate FAQs
Nearly all Hillsborough homes are detached single-family houses on large lots, often half an acre or more. Styles range from Mediterranean and Spanish Colonial Revival to Tudor, Georgian, Colonial Revival and mid-century modern, with a few landmark estates. Condominiums, townhomes and apartments are essentially absent. Many properties include pools, gardens, guest houses and mature trees, so we spend time on the land itself, including slope, drainage and boundaries, alongside the house.
Hillsborough has no commercial district at all, which sets it apart from every neighboring town. Its streets wind through hills and creek canyons, lots are large, and the town provides its own police and recreation services. Shopping, dining and rail service are in Burlingame and San Mateo. For some buyers that separation is the appeal, and for others it means more driving, which is worth testing before you commit.
Confirm whether the property sits on a public or private road and who maintains it. Review permit history, the Town’s design and building review requirements, any easements, and hillside or drainage conditions. Check wildfire hazard maps for western parcels near greenbelts and the insurance consequences. California’s Proposition 13 framework generally sets property tax at about 1% of the assessed purchase price, plus any local assessments.
The market is thin, with relatively few sales each year, so conditions vary by property. Homes priced in line with recent sales, in good condition and with a strong setting can draw several interested buyers, while overpriced listings often sit longer. Comparable sales are sparse, which makes valuation a judgment call. We plan to walk you through the nearest comparable sales and the factors that distinguish each property before you decide how to offer.
Most outdoor space here is private, in the form of large lots, gardens and mature trees. The town has small public parks, including Vista Park and Crossroads Park, and Burlingame’s Washington Park and Ray Park sit just across the boundary. County and regional open space in the hills to the west is a short drive. Buyers who want trail access should check drive times from specific streets, since the terrain makes distances feel longer.
We start with the land and the rules, not just the house: boundaries, road access, permit history and review requirements. Then we compare the few relevant sales, visit at different times of day to check traffic and noise, and coordinate inspections that include grading, drainage and trees. This site is a neighborhood guide rather than a listing search, so we work through the options with you directly.
Blakely Hull and The Best Coast Collective bring a careful, property-by-property approach to Hillsborough and the surrounding Peninsula. If you are considering a purchase or a sale, contact us to talk through your plans.
