Jessica Houlahan

With a decade of experience advising high-net-worth clients in Fairfield County and South Florida, Jessica brings a globally informed yet deeply personal approach to luxury real estate. Her strength lies not only in market insight, but in the clarity, steadiness, and confidence she brings to every client relationship — attributes that earn trust long before a transaction closes.

Jessica began her career with The Jills, the nation’s top-performing real estate team, where she developed an intimate understanding of what exceptional service looks like at the highest tiers of the market. There she learned the nuances of ultra-luxury presentation, the importance of discretion, and how to anticipate needs before they surface — skills she now brings to every listing and every negotiation.

At Cindy Raney & Team, Jessica’s advisory philosophy is simple: clients should feel informed, supported, and at ease from the very first conversation. Whether preparing a multi-million-dollar estate for market, guiding sellers through pricing strategy, or helping buyers uncover off-market opportunities, she combines strategic intelligence with genuine warmth.

Clients describe her as an advisor who listens deeply and stays two steps ahead — simplifying decisions, steadying high-stakes moments, and elevating outcomes. For Jessica, success isn’t measured solely in sales volume; it is measured in how clients feel through the process: confident in the plan, delighted with the experience, and thrilled with the result.

As a member of Cindy Raney & Team, Jessica is supported by a full-service advisory platform designed to deliver exceptional outcomes. From preparation and storytelling to negotiation and closing, every recommendation reflects intention, precision, and care — the same qualities Jessica brings to her work.

Connected to both Connecticut and South Florida, she offers a bi-regional perspective that few advisors can match, with particular expertise in luxury sales throughout New Canaan, Darien, Miami, and Palm Beach. Outside of real estate, Jessica enjoys tennis, travel, and time with her family — a reflection of the balanced, elevated lifestyle she helps her clients achieve.

For discerning buyers and sellers seeking trusted counsel, Jessica offers something rare: elite-level expertise delivered with approachability, integrity, and a refreshing commitment to doing what is right for her clients — every time.