
The Story of 4Squares
When I started my real estate career, the first brokerage I worked for was located in Central Square, Cambridge. It was here that I learned the ins and outs of the Boston-area real estate market and fell in love with the busy little squares at the heart of our local neighborhoods. Originally, the neighborhoods I knew best were Central Square, Harvard Square, Davis Square and Porter Square, and thus “4Squares” was born.
My business grew, and so did the area I served. Now, as a Medford homeowner, I appreciate the friendly bustle of Haines Square, Medford Square, West Medford and Hillside, and I want to help you find the home - and neighborhood - that fits you best, be it in Medford, Cambridge, Somerville or beyond. From apartments to condos to capes and colonials, the 4Squares Residential Group is here to help you love the way you live.

Jennifer Keenan
Medford, MA & Greater Boston Realtor®
I am a Greater Boston native and, while I love to travel, I have always called Massachusetts home. I’m proud to be a Realtor® serving buyers, sellers, landlords, and investors throughout Medford and Greater Boston. I average 40 real estate transactions a year and bring more than 17 years of experience helping clients navigate the Massachusetts real estate market.
My formal education includes a Bachelor’s degree in English from the University of Massachusetts and a Master’s degree in Management and Public Relations from Emerson College. Before becoming a Realtor®, I spent many years in the private sector, where I developed expertise in customer service, negotiation, communication, advertising, marketing, and public relations. Today, I use those skills to help my clients make informed decisions, negotiate effectively, and reach their real estate goals.
My advertising and marketing background is particularly valuable when I’m representing sellers. I know how to develop a strategic marketing plan and effectively position a property for the market—whether it’s a single-family home, condominium, apartment, or multi-family property. I’ve worked with all of them. I also understand that selling a home isn’t always about doing more; sometimes the best strategy is knowing which improvements are worth making and which ones aren't.
I am also a landlord and real estate investor, so I understand the experience of owning property from the other side of the transaction. I enjoy working with landlords and investors and bring firsthand knowledge of rental properties, multi-family homes, and the opportunities and challenges that come with real estate ownership.
I’m passionate about learning and continually expanding my knowledge of real estate, sales, marketing, and the Greater Boston market. I regularly seek out educational opportunities and attend conferences so I can bring current strategies, information, and best practices to my clients.
I have a particular connection to Medford, where I live in West Medford with my husband, Clark, and our dog, Max. I’m actively involved in the Medford community as Chair of the Medford Historical Commission and as a member of the Board of Directors for the Brooks Estate, a Victorian summer home that the City of Medford is restoring and renovating for public use.
I love living in an older home and working on its ongoing improvement, and I appreciate the character, history, and unique housing stock that make Medford and Greater Boston such interesting places to call home. When I have spare time, I love to cook, listen to music, travel, and spend time at the beach.












