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2021 Women in Real Estate
Chicago & Midwest

Maria Oliva
Three decades' experience in the senior living sector
COO of Pathway to Living since 2005
Puts an emphasis on promoting resident wellness
In the course of Maria Oliva’s 16 years at Pathway to Living—the senior housing arm of Chicago-based investor and operator Waterton–and 29 years in the senior living industry, she has been a respected leader, accessible mentor, and savvy strategist. From creating a wellness-focused operating model, to developing a multi-brand portfolio under the Pathway to Living umbrella and leading her teams through an unprecedented global pandemic, Oliva has set new benchmarks in the senior housing sector.
As Pathway to Living’s COO, Oliva always puts an emphasis on promoting resident wellness. Under her leadership, the firm implemented its signature VIVA! operating guidelines in 2009 in order to provide a holistic cultural approach to senior living, focused on resident wellness and care while catering to individual residents’ desires and abilities.
While VIVA! was created in a much simpler time, its tenets held strong through what was a period of historic change in the seniors housing sector. After the monumental challenges created by the pandemic, Oliva and her team navigated uncharted territory by taking care of not only the organization’s vulnerable residents but went above and beyond for the Pathway to Living teams.
These are just a few of the reasons we chose Oliva as one of the Chicago & Midwest 2021 Women in Real Estate Award winners. Connect CRE’s Women in Real Estate Awards honor the achievements and inspirational stories of women who have reached respected positions of leadership and play key mentorship roles for others.