Simon Collaborative Group

Sheryl, Jill and Stacy of The Simon Collaborative Group are a dedicated mother-daughter real estate team proudly serving the luxury Metro-west markets.

They have built a reputation for exceptional service, strong market knowledge, and a truly personal approach. With a blend of experience, energy, and specialized strengths, they offer their clients a well-rounded partnership rooted in trust and family values.

Sheryl, the Senior Vice President of Gibson Sotheby’s International Realty is the foundation of the team, bringing years of hands-on expertise and a steady, reassuring presence. Her deep understanding of the MetroWest market and her commitment to honest guidance have earned her longstanding client relationships. She was recognized as a top influential businesswoman in Massachusetts by Banker and Tradesman- the recipient of the prestigious Women on Fire award.

Jill adds creativity, design insight, strong organizational skills and a modern marketing edge. Her staging vision and strong digital strategies help listings shine and attract the right buyers.

Stacy’s strong networking skills, data-driven perspective and focus on pricing and market analysis, ensure a smooth transaction and ensures that every client feels informed and supported from start to finish.

Featured in numerous articles such as Wall Street Journal, Top Agent Magazine, Boston Business Journal, Boston Agent magazine, Boston Common magazine, and Weston Wellesley Magazine, The Simon Collaborative has also been recognized for many awards such as Real Trends top producing agents year after year.

True experts in their market, born and raised-and now living and raising their own families in the MetroWest suburbs. Sheryl Jill and Stacy combine their strengths to deliver a seamless, warm, and highly effective real estate experience—making every client feel like part of the family while helping them find their place in the MetroWest community.