Jessica Matthews

Meet The Jessica Collection: A boutique luxury practice on the Cascais Line — led by an American who chose Portugal for the same reasons you're considering it.

Jessica Matthews leads The Jessica Collection in Cascais. Originally from Boca Raton, Florida, she is now an American expat building a life — and a practice — on the Portuguese Riviera.

With over 15 years of professional experience in residential and commercial real estate, including investment and development, Jessica brings a strategic lens to every transaction. Her background spans the buyer, seller, and investor sides of the table, and her MBA complements a career built on disciplined deal-making and long-term client relationships.

Her client base is deliberately international. The families, executives, and investors who find their way to her are typically navigating the distance between where they are and where they are considering being — and that distance is rarely only geographic. It is language, legal systems, schooling, capital structuring, and the quiet emotional work of starting somewhere new. Jessica has done it herself. She does not underestimate what it takes.

The Jessica Collection's real estate practice operates through RE/MAX Cidadela — the most-reviewed agency on the Cascais Line, licensed by IMPIC (AMI 6100), with more than 20 years of market presence and over 4,800 families served since 2004. That partnership gives our clients the scale and infrastructure of an established Portuguese brokerage — in-house legal support, free mortgage intermediation through Maxfinance, deep agent networks for off-market access — combined with the focus of a boutique practice.

I moved to Cascais because I wanted a better version of a life I already loved. Sunlight, the ocean, good wine, real friendships, and the kind of quiet that lets you think again. My clients tend to be looking for a version of the same thing. That is what we work on, together. — Jessica Matthews