About Us

Plunkett Properties is a locally rooted real estate firm serving Winchester and surrounding communities for more than 30 years. Our team provides professional condominium property management, residential rentals, and real estate sales, helping property owners, buyers, and tenants navigate the local market with confidence.

Founded on deep local knowledge and long-standing relationships, Plunkett Properties has built a reputation for responsive service and dependable management through our full service team. We work closely with condominium boards, homeowners, landlords and renters to ensure properties are well cared for and transactions are handled smoothly.

Today, the firm continues to grow while remaining guided by the same principles it was built on—professional expertise, personalized service, and a commitment to the communities we serve.

Plunkett Properties is a three-generation, family-owned real estate firm built on over 30 years of experience serving Greater Boston communities. What began in Woburn has grown and evolved in Winchester, where we continue to deepen our roots and expand our reach. Today, our business reflects both legacy and momentum. With multiple generations actively involved, we bring a unique blend of experience, continuity, and fresh perspective to every client relationship. Our portfolio includes eight condominium communities under management, along with a trusted roster of nearly two dozen single- and multi-family property owners. As our property management foundation has grown, so too has our sales and rental division—allowing us to support clients across the full lifecycle of real estate ownership. Whether managing, leasing, or selling, we remain focused on what has defined us from the start: responsiveness, accountability, and long-term relationships built on trust.

Plunkett Properties was founded by Diane Plunkett, whose career in real estate began in Boston as a commercial broker. After gaining valuable experience in the city’s fast-paced real estate market, Diane shifted her focus closer to home, moving into property management at a Winchester-based firm where she developed a strong understanding of the needs of condominium communities and local property owners.

Recognizing an opportunity to provide a more personalized level of service, Diane established Plunkett Properties in Winchester more than 30 years ago. What began as a property management business quickly grew to include residential rentals and real estate sales, allowing the firm to support clients across every stage of property ownership.

Over the years, Plunkett Properties has built lasting relationships with condominium boards, landlords, and homeowners throughout Winchester and the surrounding towns. Those relationships—and the trust behind them—have been the foundation of the firm’s growth.

Today, the company has evolved into a multi-generational family business. Diane’s daughters are actively involved in the firm’s real estate sales and rental operations, continuing the tradition of hands-on service and deep local expertise. The next generation is now joining as well, with grandson, Nick Ricci, supporting the business as a licensed realtor and granddaughter, Ava O’Connor, taking on marketing and social media initiatives while attending college.

While the team has grown over the years, the philosophy behind Plunkett Properties remains the same: provide knowledgeable guidance, responsive service, and a level of care that reflects the firm’s deep roots in the community.

For three generations, Plunkett Properties has remained committed to helping clients manage, rent, buy, and sell homes with confidence—combining professional expertise with the personalized attention that has defined the firm from the beginning.