About Jessica Silipo

Jessica Silipo is a Winchester, Massachusetts real estate agent with Kim Covino & Co. at Compass, the #1 real estate team in Massachusetts by sales volume according to RealTrends Verified rankings based on 2025 sales data.Born and raised in Winchester, Jessica continues to call the town home and brings firsthand knowledge of Winchester, Greater Boston and the North Shore to every client she works with.

Known for her strong work ethic, attention to detail and thorough understanding of the local real estate market, Jessica is a trusted resource for both buyers and sellers. Her deep roots in the community, combined with her knowledge of surrounding towns and neighborhoods, allow her to provide valuable insight throughout every step of the buying or selling process.

Jessica’s passion for architecture, decorating and remodeling brings another level of expertise to her work. Buyers often rely on her eye for design to identify homes with potential and envision what a property could become, while sellers benefit from her ability to recognize improvements that can enhance a home’s presentation and appeal.

Whether buying or selling in Winchester, the Greater Boston area or the North Shore, Jessica combines local expertise, market knowledge and a great eye for design to help her clients make confident real estate decisions.