By: William Jones
Sarah C. Jaffe is a Chicago-based real estate broker who has built her career around a clear principle: buying or selling a home is one of the most significant financial decisions a person can make, and it deserves to be treated as such, not simply as a transaction to be completed.
Based on the city’s North and West Sides, Sarah partners with clients who expect more than access; they seek thoughtful guidance, strategic insight, and a comprehensive understanding of the market. She is known for helping clients navigate the full scope of the process with clarity and confidence, ensuring every decision is both informed and intentional.
Since starting in real estate in 2020, Sarah has built a strong track record of closings across Chicago’s most sought-after neighborhoods. In 2025 alone, she ranked among the city’s most productive residential brokers. What makes that performance notable is that all of her business comes from past client referrals, word-of-mouth, and organic social media leads, as opposed to many brokers who pay for their clients. For Sarah, real estate is not about volume for its own sake. It is about building relationships that last well beyond a single closing.
A Focus on First-Time Buyers
A large portion of Sarah’s business comes from first-time buyers, people navigating the complexity of the Chicago market for the first time and looking for someone who will take the time to explain how it all works. She specializes in properties in the $750,000 to $2 million range and approaches each relationship with a long-term view.
“I am not a glorified door opener,” Sarah explained. “I am a long-term strategic advisor, just like a CPA or financial planner. Real estate is the largest financial asset most people will own, yet the industry often treats it as a short-term sales process.”
Her clients tend to be high-performing professionals who want to understand the reasoning behind every decision. They are smart, busy, and often overwhelmed by all the variables involved in buying or selling a home. Pricing strategy, neighborhood dynamics, renovation potential, timing. There is a lot to consider, and Sarah sees her role as translating all of that into clear, actionable guidance. She brings a no-nonsense perspective and a highly organized approach that removes friction from what can otherwise be a stressful experience.
Seeing Beyond the Present
Sarah also thinks about homes differently from many agents. Rather than viewing a property as a finished product, she encourages clients to consider how a space can evolve over time. She collaborates with designers, architects, and contractors to help buyers see the potential in what they are purchasing, both for their daily lives and for future resale value.
“My clients are highly informed professionals who want to understand the ‘why’ behind every decision,” she said. “My role is to translate complex market information into clear and strategic guidance.”
The ideal outcome, in her view, is that clients walk away feeling confident, informed, and genuinely excited about their decision. Not just about the home itself, but about how it fits into their broader life and financial goals.
Growth at Cross Street
Sarah joined Cross Street in February 2024 and has taken on leadership responsibilities within the brokerage. She recently formalized her role as Partner, Head of Sales, alongside managing broker Michael Horwitz. Together, they are shaping the direction of the sales division and building an environment that supports other brokers who share a sales-forward mindset.
Cross Street itself has been growing. Earlier this year, the brokerage incorporated Peak Properties into its nationwide business, expanding its residential brokerage and development operations while adding property management services. The combined portfolio now includes nearly 12,000 apartments across Chicago, Denver, and Cleveland. Peak will continue operating locally under its own name, but both companies now share the same back end for operations.
Building Wealth, Community, and Beautiful Spaces
Outside of her work, Sarah has a deep appreciation for architecture, design, and travel, interests that naturally inform her perspective on real estate. She remains actively involved with local nonprofits and is also an investor in Chicago, giving her both a professional and personal stake in the city’s growth.
For Sarah, real estate extends far beyond the transaction. It is a means of building long-term wealth, strengthening communities, and creating spaces that are as thoughtful as they are livable.
“My goal is for every client to walk away knowing they had a trusted expert in their corner at every step of the process,” she says.
In an industry that often prioritizes speed over substance, Sarah has intentionally built her business differently, grounded in education, transparency, and the belief that well-informed real estate decisions should compound in value over time.
