A Multi-Generational Family Move
- Jan 8
- 4 min read
Welcome to Behind the Before & After | Buying and Selling - where I share, step-by-step, how I help all kinds of buyers and sellers reach their real estate goals. Whether you're downsizing, out-growing a home, or house hunting for the very first time, I know the challenges, and I know how to help you through them! Below, A Multi-Generational Family Move -
How We Met | In Medford, of course!
Buyer F came to me because she and her parents wanted to combine households, and - hopefully - buy a home together in the Boston suburbs. Her parents had moved to Massachusetts from the mid-west during COVID. They now lived in the western part of the state, where they had a farmhouse with lots of land, while their daughter had a condo in Melrose.
But after living like this for more than four years, with all of them driving back and forth to visit, they collectively decided that it would be better for everyone to move closer to Boston. The whole family valued walkability as well as access to public transportation, and while the parents were retired, their daughter wanted to be close to work in Medford. The goal was for both the parents, and their daughter, to sell their separate homes, and then purchase a home together where the family could all live under the same roof.
The Challenges | Timing and Communication
When Buyer F and I initially met, we needed to come up with a plan so that no one would be homeless at any time during the three transactions - selling the parents’ property in Western Mass, selling the daughter’s condo, and buying the new family home.
I had Buyer F get pre-approved for a mortgage so that we could find out if she could buy a new house using her income and the proceeds of the parents’ sale. Thankfully the numbers worked and our plan was in place - her parents would sell their property first, while we were out shopping for a new home for the whole family.
Selling the Parents’ Property
Our next step was to get Mom and Dad a real estate agent in Western Mass, and I was able to refer them to a great agent who understood the complex timing of this particular move.
The Search
The family was interested in buying either a multi-family property, where each household could have their own apartment, or a single-family home, that could be broken up into distinct living areas. We looked at a variety of properties, all convenient to Boston and to the daughter’s job in Medford. Ultimately we were able to find a house in nearby Malden - in their budget - that had a layout that worked for the whole family - and the big fluffy family dog.
Things Come Together
We put an offer in on the home, subject to the sale of the parents’ property in Western Mass. The Malden seller was amenable to this contingency because he understood the process of the combined households. At this point, we were under contract to sell the property in Western Mass and to purchase the new home, at the same time.
Photos, clockwise from top left: A big fluffy dog needs some room, more space than the daughter's condo had to share, the house (and yard) that fit this family's needs, the remote beauty of Western Massachusetts.
Selling the Daughter’s Condo
Now, we were able to focus on getting Buyer F’s little condo on the market. We did an amazing photo shoot and virtual staging, and had lots of interest right away.
The Outcome
In a transaction like this it is imperative that there is an overarching plan and impeccable communication. As the family’s agent I needed to keep tabs on the listing in western Mass and the process for the sale there, as well as the purchase in Malden, and the daughter’s local condo sale. Everyone involved in the three transactions - buyers, sellers and their agents - wanted to know what would happen next. Now, my clients - Buyer F and her parents - are living under one roof with access to public transportation, a short commute to work AND a yard for their dog. And they are making improvements to their new multi-generational home using the proceeds from the condo sale.
Hear from the daughter (below) and (below that) her parents -
Buying/Selling a home is a BIG deal. There are so many things you have to do at the right time, in the right way and if you want to take some of the stress out of your home buying experience, Jen is the Realtor for you! We had a weird multi-property sell and a weird timeline. I was not sure it was even possible to do but Jen helped my family navigate the whole process quickly! So, if you have been scrolling Zillow for days and thinking “I can’t ever” … stop that. Go talk to Jen. You won’t regret it.
Jennifer Keenan helped us with each step through a multi complex plan. My husband and I downsized, our daughter sold her condo, and we purchased a house together. Jennifer helped us with everything even using her connections to help us sell in western massachusetts. She listened and professionally advised each of us. Thank you again for the success.
For this and all my online reviews, please see my Google Business page. For more case studies of how I help buyers and sellers, explore my whole series Behind the Before & After | Buying & Selling.













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