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Jennifer A. Deland

Trusts Attorney at Holliston, MA

5.0   5 reviews

also known as Deland Law Office

  • Licensed for 32 years
    State MA
    Acquired 1991
    Active No misconduct found

We have not found any instances of professional misconduct for this lawyer.

About Jennifer

Learn Jennifer’s areas of practice.

I have been practicing law in Massachusetts since 1990.  I came here to go to lawschool - Boston University.  I graduated,  magna cum laude (somewhat to my own surprise) from B.U. and when back, as I had planned, to New York City, but Massachusetts drew me back.    I came back to Massachusetts to work for a firm here, and then, in 1991 I came out on my own as solo practitioner.  For awhile I took whatever came in the door, including real estate, bankruptcy and divorce.  But I soon focused on estate planning.  It has everything I want - property, business, interesting legal questions, and something I hadn't realized the importance of in my practice - interesting people.  My passion is to help people arrange their property to accomplish their own goals.  In the process, I get to learn a lot about those goals, and about the lives and families of my clients.  They are all different, and all wonderful!

Photos and videos

The view from my office, across to the Holliston Post Office


Jennifer A. Deland
1660 Washington Street
Holliston, MA, 01746

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5.0 / 5.0
  5 customer reviews
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1 Star
Posted by K.C. | December 6, 2021
This review is from a person who hired this attorney.
| Hired Attorney
After living a largely lawyer-free life, my wife and I found ourselves looking for legal services as we tried to manage estate details that my wife faced as the executor of her mother’s will. Living in Holliston, we gave Jennifer a call and explained our situation. Ken, who works with Jennifer, guided us through probate court procedures and helped my wife settle the estate with her siblings. This experience got us thinking of our own estate planning (we had none at the time), so we asked Jennifer to help us put our wills together and establish a trust for our assets. Despite the coincidental onset of the pandemic, we were able to conduct meetings over Zoom with Jennifer, who patiently explained to us and helped us address health care proxies, powers of attorney, powers of attorney for tax matters, life trusts, income trusts, last wills, and memorial arrangements—topics about which we had only limited knowledge. Throughout the process, Jennifer provided clear guidance so that our own estate plan now suits our needs. As a result of our experience, we have gladly retained Jennifer as our lawyer, and when we recently met to follow up on some details of our trust, making sure that everything is in place, Jennifer found a few little things to address and is helping us explore a tax rebate for our newly installed septic system. Knowing we have such an advocate certainly gives us peace of mind.
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Posted by Debbie | June 4, 2019
This review is from a person who hired this attorney.
| Hired Attorney
Excellent Estate Planning
I worked with Jennifer over the past 8 months, pulling together everything needed to create an estate plan, as well as Power of Attorney, Health Care, and Will. I love how she broke it up into "bite size pieces", and each month would give me something to think about, a list of papers to bring in, etc. What could have been daunting was made to be palatable. I now have everything complete, and totally organized in a great binder! Its some of the best money I've spent!
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Posted by Richard | May 1, 2014
Estate Planning with Jennifer Deland
My wife and I have worked with Ms Deland since 1997 setting up our estate trusts. She has always been knowledgable and provided us with good advice. She has helped us deal with various accounts including 529's for grandchildern, IRA's and several banks.
Posted by Janice | February 25, 2014
Elder Law Made Easy
Jennifer Deland is very knowledgeable and easy to work with. She explains everything in terms that I can understand. All issues are reviewed as slowly as needed for me to feel confident in my decisions. The finished documentation is done in impeccable condition, and totally organized. I have every confidence in her having my best interest in mind at all times.
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Posted by Marilyn | November 16, 2011
Recommendation for Jennifer Deland
Over the past two years Jennifer Deland has done my estate plan and helped me to get my financial affairs clarified and organized. Since I am a fairly recent widow and still dealing with the effects of grief, the task was daunting and overwhelming for me. Jennifer broke it down into manageable parts so that we were able to make plans and proceed in a step wise manner. It is such a relief to have the finances in order now and into the future! Jennifer's attention to detail is wonderful and she has been very responsive to questions and suggestions. Her advice is clear, concise, thoughtful and directive. Jennifer teaches as well as advises so that the mystery of the legality of the process was gone. One of the most interesting aspects of our relationship is that Jennifer can tell when I am in overload and she does not force me beyond my capacity to deal with the situation at the time. My experience with her has been very positive and worthwhile and I heartily recommend her to anyone undertaking these endeavors.
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Contact for Details


AVVO RATING 8.1 (Excellent)

Work Experience

  • Attorney
  • Deland Law Office
  • 2008 - Present


  • Boston University School of Law
  • JD - Juris Doctor
  • 1986

Sample of Legal Cases

  • Medicaid with a twist
  • Masshealth Long-Term Care approved
  • Helping the Sons Help their Mother
  • She signed a Life Trust, Powers of Attorney, Health Care Documents and a will


  • National Academy of Elder Law Attorneys (Massachusetts Chapter)
  • Member
  • 2008 - Present

Languages Spoken

  • English


Speaking Engagements

  • Massachusetts Online Seminar
  • Trusts 101
  • 2021
  • Worcester Property Owners Association Meeting
  • Asset Protection for Real Estate
  • 2012

Attorney endorsements

Received (9)
Given (20)
Endorse Jennifer
Estate planning Attorney | Jun 10
Relationship: Fellow lawyer in community
"I endorse this lawyer. Jennifer is extremely knowledgeable and uses top-notch estate planning solutions for her clients. At the same time, she has a knack for communicating legal issues into down-to-earth client friendly language."
Elder law Attorney | Jan 20
Relationship: Fellow lawyer in community
"I endorse this lawyer. Attorney Deland is an outstanding attorney with an exceptional reputation. She is a credit to the legal community and I highly endorse her legal services!"
Estate planning Attorney | Jun 24
Relationship: Fellow lawyer in community
"As a fellow Elder Law and Estate Planning attorney I happily endorse Jennifer. She is a conscientious and diligent attorney who brings considerable talent and expertise to the benefit of her clients. She is a credit to the legal profession and we need more life her serving the public."
Elder law Attorney | Aug 09
Relationship: Fellow lawyer in community
"I endorse this lawyer."
Estate planning Attorney | Oct 28
Relationship: Other
"I endorse this lawyer."
Elder law Attorney | Sep 11
Relationship: Fellow lawyer in community
"Attorney Deland is an oustanding attorney who provides quality legal advise to her clients. She is dedicated and passionate about the law. I highly endorse her!"
Unknown Attorney | Mar 09
Relationship: Fellow lawyer in community
"I endorse this lawyer. She provides detailed and insightful analysis to questions posed by AVVO subscribers. The detailed responses and thorough explanations provided here display a vast knowledge of the law. She is an asset to the legal community.."
Estate planning Attorney | Jan 22
Relationship: Fellow lawyer in community
"Attorney Jennifer A. Deland is a practical, knowledgeable, and articulate advocate with substantial legal experience. More to the point, she represents his clients with passion, commitment, and professional acumen. I endorse attorney Deland with enthusiasm."
Unknown Attorney | Dec 28
Relationship: Fellow lawyer in community
"I endorse this lawyer."
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