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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.

About Jennifer Keenan

I am a greater Boston native and while I love to travel, I have always called Massachusetts home. My formal education includes earning a Bachelor's degree in English from the University of Massachusetts and a Master’s degree in Management and Public Relations from Emerson College. 


As a Realtor®, I average 40 transactions a year for buyers, sellers, and landlords. After many years in the private sector, I am an expert in customer service, negotiations, and communication - skills I use to help you reach your real estate goals. My background in all things advertising enables me to effectively market your property - be it a single-family home, condo, apartment, or multi-family, I've done it all. I am passionate about learning and gaining new skills, and I regularly seek out educational experiences and attend conferences, so that I can share the best strategies and tactics in real estate and sales with you. 


I am also a landlord and investor, and I enjoy improving my vintage home in West Medford, where I live with my husband Clark, and our dogs, Dallas and Max. I’m involved in local government; I am the Chair of the Medford Historical Commission and serve on the Board of Directors for the Brooks Estate, a Victorian summer home that the city of Medford is restoring and renovating for public use. When I have spare time, I love to cook, listen to music, and spend time at the beach.

  • How much of a down payment do we need to buy a home? We don't have 20% - does this limit our buying power?
    Many home buyers believe that they won't qualify to buy a home if they don't have a 20% down payment. In reality, the average first-time homebuyer puts down just 6%. As a buyer agent, I connect homebuyers to lenders offering loans that require as little as 3% down & sometimes zero down. My goal for you is to become a homeowner on your terms. If that means you can get approved for a house with a smaller down payment and become a homeowner sooner, that's often the right choice. Have more questions? Contact me to discuss your options.
  • I have tenants who are in the midst of house hunting. How can I ensure that I can get a tenant when they purchase a home?
    Great question! No doubt you are happy for your tenants - I think we can all agree that becoming a homeowner is a positive step for those tenants. Communication is key here. Just because they are house hunting does not necessarily mean you will be left high and dry without rent. First, it will depend how quickly they find something. When that happens (and depending on how much time is left on the lease), I always advise all parties to have a conversation about how best to move forward. Options could include a settlement, a subletter, or perhaps their timing is perfect for you to get into the unit and make some needed repairs or renovations. They want to move. You don't want to miss out on rent. There is always a way to work it out! And when in doubt, give me a call and we can talk through your specific concerns. ;)
  • Should we rent in a new area before committing to buying a home there?
    Renting is a great way to get a feel for an area, especially if you are unsure of a neighborhood, school system, or job commute. Renting is also a great way to try a different style of living - whether you are downsizing and want to try a condo, or if you are done with maintenance and want to have an apartment and a landlord to take care of everything.
  • My friends used the Seller's agent to buy their house and got a discount. Why do I need my own agent?
    A Seller's agent only has one job - to get the Seller the best terms and highest price for their home. They have fiduciary responsibility to their client only. Although they, by law, have to treat any unrepresented Buyer ethically and fairly, Seller Agents have no fiduciary duty to that Buyer to ensure they get the home for the Buyer's best price or terms. When you work directly with the Seller's agent, you are essentially hiring someone to work against you. As an Accredited Buyer's Representative®, I have the knowledge and experience to make your dream of buying a home a reality, and I am serving you, not selling you in the process. Learn more about how Buyer Agency works by emailing me at for a copy of my "Love the Way You Live Home Buyer's Guide."
  • What COVID precautions are sellers taking at Open Houses?
    As of June 2021 these precautions have been lifted - however, 4Squares will continue to respond to our community's health situation and any future regulations. At my open houses, I am working with the Sellers to ensure maximum safety, both for the homeowner and the open house attendees. I am collecting contact information for all attendees should we need to contact anyone after the fact. Everyone must use hand sanitizer upon entry as well as wear a face mask. Lysol wipes are used as a barrier to open closets, cabinets, and hand rails. Depending on the size of the property, no more than 2 or 3 parties in total in the house at any time, and make sure the attendees are spread out throughout the house/not sharing the same rooms at the same time. Lastly, when possible, have all attendees use a "one way" system - so everyone is coming in the front door and out a back or side door to ensure a smooth flow of traffic. ​ I also offer virtual tours, and I'm always happy to arrange a private showing that respects the privacy & safety of all parties - at any property.
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