Olivia Massimino

With more than 20 years of experience across real estate, development and estate management, Olivia brings a depth of perspective to Boulder County’s residential real estate market. As Owner and Principal of Massimino Development, she has spent more than 16 years guiding residential and mixed-use projects representing nearly $300 million in capitalization, with expertise spanning site acquisition, entitlements, architecture and design, construction and project oversight. Her background gives her a developer’s eye and the ability to recognize the craftsmanship and design decisions that create value while seeing potential others may overlook.

Olivia’s approach is strategic, hands-on and deeply personal. She believes clients deserve to understand not only what she recommends, but why, bringing a candid perspective and careful attention to the details that shape a transaction and a home’s long-term value. Her expertise is particularly well suited to distinctive, design-conscious properties and clients navigating renovation, construction or the nuances of positioning a home for market. Whether evaluating a finished residence, considering the potential of an existing property or envisioning what could take shape on a blank piece of land, Olivia helps clients move forward with clarity and confidence.

To Olivia, Boulder County is home. She has lived in South Boulder, East Boulder, Gunbarrel and Louisville, raised her three children here and remains deeply connected to the community as a CU Boulder alumna. Her appreciation for architecture and design extends beyond her professional life, shaped by travel, gardening and a shared passion for real estate with her husband. Drawn to milehimodern for its sophisticated brand, design-forward perspective and collaborative culture, Olivia brings together her development expertise and intimate understanding of Boulder County to offer a thoughtful, highly personal approach to residential real estate.