Ranking the most expensive cities in the Bay Area. Data based on Single Family Homes as of the end of November, 2022. Atherton (San Mateo County) $9,547,815 Rutherford (Napa County) $9,225,000 Ross (Marin County) $6,566,429 Hillsborough (San Mateo County) $6,436,419 Los Altos Hills (Sant Clara County) $6,301,250 Woodside (San Mateo County) $5,950,658 Belvedere (Marin County) $5,878,282 Portola Valley (San Mateo County) $5,421,496 Monte Sereno (Sant Clara County) $4,525,924 Los Altos (Sant Clara County) $4,437,010 Stinson Beach (Marin County) $4,379,833 Tiburon (Marin County) $4,234,628 Kentfield (Marin County) $4,117,720 Palo Alto (Sant Clara County) $4,067,152 Saratoga (San