About Michelle Wininger

Michelle believes exceptional representation should define every experience.

With a career spanning Connecticut’s shoreline and the Florida Keys, she advises buyers and sellers of waterfront properties with a discreet, highly tailored approach. Since 2009, her business has been built on thoughtful strategy, precise positioning, and a deep understanding of timing; earning the trust of clients navigating significant transitions, from second homes to legacy properties.

Her connection to the Florida Keys was personal long before it was professional. Drawn to its quiet beauty and unassuming luxury, she found a lifestyle that reflects what she values most: privacy, authenticity, and ease. That perspective shapes how she represents her clients—calm, intentional, and always aligned with their greater goals.

Michelle’s approach blends data-driven insight with intuition, allowing her to guide with both clarity and instinct. She is known for creating opportunities beyond the public market and for delivering an experience defined by discretion, trust, and thoughtful execution.

Working seamlessly between the Northeast and the Florida Keys, she brings a far-reaching network and a refined understanding of two distinct coastal markets, connecting people not just to properties, but to a way of living.

Outside of real estate, Michelle is deeply committed to animal rescue and shares her home with her two rescue pit bulls, Duke and Sasha. She spends her time on the water, embracing the simplicity of island life, and enjoying quiet moments with her partner, Mark, often with a glass of wine in hand.

Because to Michelle, real estate is never just about where you live, it’s about how you live.