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For more than 30 years, Plunkett Properties has been a trusted name in Winchester/Woburn real estate. As a three-generation, family-owned firm rooted in the community, we bring deep local knowledge and hands-on expertise to everything we do—from managing condominium communities and investment properties to helping buyers, sellers, and tenants navigate the market with confidence. Whether you’re a condo board seeking reliable property management, a homeowner preparing to sell, or a renter searching for your next place to call home, our team is committed to delivering responsive service, lasting relationships, and real results across Winchester, Woburn and the surrounding towns.

See Why Our Clients Love Us

Client Reviews

"Plunkett Properties is a great family business to work with. Lynn and Sheri helped me sell my house in Burlington. They are very professional, prompt, and have great ideas for staging my house. For the open house, Lynn went above and beyond in doing an illustration or sketch of the backyard with a deck and sliders to show potential buyers what they could build off my dining room. I have also bought and sold a house with Plunkett Properties in Chelmsford. While looking, Lynn was my Buyer's Agent – she and I would go to view open houses or scheduled viewings of homes. Lynn would bring her experience and knowledge to the showings, and we'd look at places with different viewpoints. It has been a pleasure working with Lynn and Sheri."
"Plunkett Properties is a great family business to work with. Lynn and Sheri helped me sell my house in Burlington. They are very professional, prompt, and have great ideas for staging my house. For the open house, Lynn went above and beyond in doing an illustration or sketch of the backyard with a deck and sliders to show potential buyers what they could build off my dining room. I have also bought and sold a house with Plunkett Properties in Chelmsford. While looking, Lynn was my Buyer's Agent – she and I would go to view open houses or scheduled viewings of homes. Lynn would bring her experience and knowledge to the showings, and we'd look at places with different viewpoints. It has been a pleasure working with Lynn and Sheri."
J. A.
"Working with Plunkett Properties was an absolutely fantastic experience from start to finish. She was knowledgeable, professional, available, and always had my best interests in mind throughout the entire process. Buying a home can be stressful, but Lynn (Plunkett) Ricci made everything feel smooth and manageable by keeping me informed every step of the way. Lynn's attention to detail, quick communication, and deep understanding of the market really stood out. Anytime I had questions, she responded promptly and made sure I felt confident in every decision. It truly felt like Lynn went above and beyond to make sure everything worked out perfectly. I would highly recommend Lynn, Diane, and Plunkett Properties to anyone looking to buy or sell a home. If you want someone who is dedicated, trustworthy, and genuinely cares about their clients, this is the realtor you want on your side. Thank you for making this such a great experience!"
"Working with Plunkett Properties was an absolutely fantastic experience from start to finish. She was knowledgeable, professional, available, and always had my best interests in mind throughout the entire process. Buying a home can be stressful, but Lynn (Plunkett) Ricci made everything feel smooth and manageable by keeping me informed every step of the way. Lynn's attention to detail, quick communication, and deep understanding of the market really stood out. Anytime I had questions, she responded promptly and made sure I felt confident in every decision. It truly felt like Lynn went above and beyond to make sure everything worked out perfectly. I would highly recommend Lynn, Diane, and Plunkett Properties to anyone looking to buy or sell a home. If you want someone who is dedicated, trustworthy, and genuinely cares about their clients, this is the realtor you want on your side. Thank you for making this such a great experience!"
Brian
"Plunkett Properties is a great real estate office. I was temporarily living in an apartment for over a year because my condo sold, and the market where I moved was very challenging to get an accepted offer. So, to say I was stressed out finding housing was an understatement. Sheri is a very low-key, no-pressure agent and goes above and beyond to make sure the house is a fit. She worked with me on my preferences and locations and was always sending me properties to look at/make appointments to visit. I had other agents trying to get my business, and then would tell me to contact them when I'd find something, and they'd show me, which is crazy that I'd have to do all the up-front legwork. Sheri also ran down house permit history (without asking), actively engaged with the home inspection findings, and, because Plunkett Properties also does property management, she had contacts (if I didn't) that followed up on the findings. She also checked a number of other things that other agents I've had in the past either didn't do or missed. I am very happy with my house and would definitely use them again and recommend them. "
"Plunkett Properties is a great real estate office. I was temporarily living in an apartment for over a year because my condo sold, and the market where I moved was very challenging to get an accepted offer. So, to say I was stressed out finding housing was an understatement. Sheri is a very low-key, no-pressure agent and goes above and beyond to make sure the house is a fit. She worked with me on my preferences and locations and was always sending me properties to look at/make appointments to visit. I had other agents trying to get my business, and then would tell me to contact them when I'd find something, and they'd show me, which is crazy that I'd have to do all the up-front legwork. Sheri also ran down house permit history (without asking), actively engaged with the home inspection findings, and, because Plunkett Properties also does property management, she had contacts (if I didn't) that followed up on the findings. She also checked a number of other things that other agents I've had in the past either didn't do or missed. I am very happy with my house and would definitely use them again and recommend them. "
Sara
"Working with Sheri O'Connor at Plunkett Properties was truly a wonderful experience for our family. What started as a long and sometimes tedious journey to find the right home ended up being a smooth and positive process thanks to Sheri's dedication, patience, and expertise. Throughout the process, Sheri was always responsive, knowledgeable, and incredibly supportive. Whether it was scheduling showings, explaining details we didn't understand, or helping us navigate the paperwork and negotiations, she made everything feel manageable. Her attention to detail and her commitment to her clients truly stand out. Thanks, Sheri, for taking the time and energy to help us find our forever home."
"Working with Sheri O'Connor at Plunkett Properties was truly a wonderful experience for our family. What started as a long and sometimes tedious journey to find the right home ended up being a smooth and positive process thanks to Sheri's dedication, patience, and expertise. Throughout the process, Sheri was always responsive, knowledgeable, and incredibly supportive. Whether it was scheduling showings, explaining details we didn't understand, or helping us navigate the paperwork and negotiations, she made everything feel manageable. Her attention to detail and her commitment to her clients truly stand out. Thanks, Sheri, for taking the time and energy to help us find our forever home."
The McGuires

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