About Us

Plunkett Properties

For ALL your housing needs!
We are available to help in every area of your real estate needs and look forward to working with you.

I started my career in real estate over 35 years ago selling both Commercial and Residential property in Boston, focusing in the North and South ends during the 80’s real estate boom. I then took a few years off and returned to the market in residential sales and rentals in the Winchester/Woburn area. I opened the doors to my new company in 1996 in Woburn MA with my daughter, Sheri O’Connor. While Sheri handled most of the sales and rentals, I concentrated on property management including single family, multi family and condominiums. The business grew quickly thanks to our happy customers. In 2002 we moved the office back to Winchester.

Diane C. Plunkett


To meet the needs of the homeowner, we take the time to learn about them. We help them decide if it is the right time to sell, if there are options to consider and what might be needed to market the property in the best light. Our team of experts can assist in preparing the property and the rest is up to us to advertise, hold “Open House” as often as possible and to negotiate on behalf of the seller.

For our buyers, we help prepare a “wish list”, assist in pre-approval for a mortgage, and start the search for their dream home. It is our job to point out the pros and cons of each property to be sure the buyer has all the facts to make their decision.


This is a big part of our business including many condominium complexes in Winchester. We have a full service team of professionals, available 24 hours if necessary, with the knowledge to handle every aspect of maintenance. We can manage one unit or an entire complex with the same efficiency. Many landlords do not want to be involved in the day-to-day management of their property and they depend on us to collect and deposit rents, provide emergency service when needed and to oversee cosmetic updates between tenants.


Finding the right tenant for the right property is all about the “right fit”. This is even more important than finding a buyer for the property. When a landlord turns over the keys to a stranger to live in his house, his big investment, it is a leap of trust. We promise landlords that we will process the applications carefully checking not only their credit but the previous landlords and employment. We arrange a meeting between both parties and we prepare a customized lease for that property. Helping our customers to find a new home is a responsibility we take very seriously.

We will get you home quicker

We take our tagline very seriously and for the last 30 years have been committed to finding you the perfect home – whether renting or buying. I have also built the largest property management firm covering Winchester properties as well as work with property owners in the area to assure the best for you and your investment.  We look forward to meeting you and finding you your perfect place.

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from our team.

You have Successfully Subscribed!