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Jennifer B. DaSilva

Senior Sales Associate | REALTOR®
Massachusetts licensed real estate salesperson
(774) 355-5745(office)

Jennifer has deep family roots and lifelong friends on Martha’s Vineyard. Her family began vacationing in Oak Bluffs in 1958 and she has spent over 35 years summering here. 

After a successful career practicing international corporate law in New York City and New Jersey, owning a small business and family mediation practice in the Boston area, serving as an elected public official in Dover town government, and raising her children, Jennifer decided to pursue her passion for real estate when she and her friend who built her Vineyard home, began to discuss real estate opportunities. 

A new development called Preserve at the Woodlands was selling 2 to 4-acre vacant land lots in Oak Bluffs. They formed a company, bought two lots, and built the first house from the ground up there. Jennifer joined the HOA Board, helped to create the subdivision covenants, and establish the Preserve community. Simultaneously her friends began to ask her for MV real estate advice and she decided to get her real estate license and pursue a career in sales in addition to development.

“It is a wonderful feeling, like matchmaking, helping my clients find their perfect home in my happy place,” says Jennifer. Jennifer, who enjoys utilizing her strong negotiation, analytical and interpersonal skills in her busy, encore real estate career. Her passion, professionalism, and dedication have placed her as one of the top agents on the Island with approximately $28 million in sales in 2022.

Jennifer is heavily involved in Vineyard life and serves as a non-profit Board member of both the Martha’s Vineyard Boys and Girls Club and The Cottagers, Incorporated. Jennifer also gives back through philanthropic activities as a member of The Links, Incorporated, and Alpha Kappa Alpha Sorority, Incorporated. She is a graduate of Duke University and Columbia University School of Law.  

Jennifer and her husband bought land in Edgartown over 20 years ago and subsequently built their home there. They love the process of building and renovating and are involved in other real estate projects on the island. For fun, Jennifer enjoys travel, playing tennis, and reading. She lives in Edgartown with her husband.



ABR - Accredited Buyer Representative

SRS - Seller Representative Specialist

RSPS - Resort and Second-Home Specialist

PSA - Pricing Strategy Advisor

SFR - Short Sales and Foreclosures Resource


Client Reviews

"Simply put, Jennifer is amazing and exceeded my every expectation.  Not only is she incredibly knowledgeable, responsive, professional, detail-oriented, and diligent but she also has amazing instincts.  She keenly advised me on the timing of my offer and through the bidding process so that I was able to secure my dream home.  She also has great relationships with the other agents on the island which made the house viewing process seamless.  In addition, Jennifer has a huge network and is able to provide referrals on just about anything needed during the home buying process from a lawyer to an insurance agent.  If you are looking for an amazing realtor in Martha’s Vineyard look no further than Jennifer!"

Tiffany S

"Jennifer came highly recommended to us from close friends who had just purchased a home on the island. After working with her I now understand why my friends hold her in such high regard. Jennifer is a great agent and a great person. She really cares about her clients, is meticulous, and takes care of all the details. Communication was great and she was always available for a late-night phone call or text. Despite the fact we didn’t know exactly what we were looking for Jennifer was patient and informative as we visited multiple homes just waiting for 'the right feeling to hit us.'  When it finally did 'hit us,' Jen made sure we got our dream home and was there every step of the way thru closing and still remains an invaluable resource as we make the home perfect for us"

Eric V

"We gave Jennifer 5-stars and if there were 10 we would give her all 10. After many years of spending a few weeks each summer on the Vineyard, we finally made the decision to purchase our own home here in the summer of 2018. After speaking with several different realtors, we chose Jennifer DaSilva and we could not have been happier with our choice. She took the time to understand our needs, made sure we knew what was happening with the market when we were not on the Island, and helped us avoid some very costly 'rookie' mistakes when buying a home on the Vineyard. We love our Vineyard home and are now starting to work with Jennifer to find a second one!!! She's that good!"

Gena A

"With Jennifer’s help, we found a home that checks all the boxes! Her flexibility and willingness to make the best use of the limited time we had allowed us to leave feeling confident we had made the right choice in making an offer. Her skilled guidance in negotiating also helped us confidently go through the process and come out with the home we had dreamed of. Her help continues as she provides resources and advice as we move forward in purchasing furniture and doing some renovations to truly make this home ours. Thank you, Jennifer, for all your help!"

Debbie O

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