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About Matthew

Matthew Winterle Duxbury, MA Real Estate Agent Headshot

Matthew Winterle

Luxury Real Estate Advisor I Broker

Get to Know Me

Matt Winterle has been a real estate professional for over 20 years. He started his career in commercial real estate appraising before co-founding the Boston-based real estate brokerage Boston Condo Group, LLC in 2006. Matt was the company’s Lead Broker-Owner and Director of Marketing from 2006 to 2017. Over this time, he helped buyers, sellers, and investors purchase and sell real estate in the City of Boston and throughout all of eastern Massachusetts, including the Cape and the Islands. Matt has earned the real estate designations of Accredited Buyer Representative (ABR), Real Estate Negotiation Expert (RENE), and Graduate of the REALTOR® Institute (GRI). 

A long-time resident of Duxbury, MA, Matt lived in Boston for about 12 years before moving back to Duxbury with his family in 2015. He joined LAER Realty Partners and opened the first LAER LUX office in Duxbury in 2020 and was in the Top 1% in sales at the brokerage (of over 600 agents) from 2020 to 2025. Now with The Carucci Group and SERHANT, Matt continues to represent buyers and sellers in and around the Boston area, the South Shore, Cape Cod, and the Islands.
 
Prior to beginning a career in real estate, Matt received a degree in economics from Bates College in Lewiston, Maine, where he was also Captain of the Bates Men’s Lacrosse team. More recently, Matt received his MBA from the F.W. Olin Graduate School of Business at Babson College.
 

Why Me?

Over the past 20+ years, I have helped clients all over eastern Massachusetts through the home-selling and buying process. My experiences in a wider geographic area, with a highly diversified client base, and my passion for continuous self-education have helped me to stay ahead of the competition. I’m committed to exceeding expectations at every step, creating a truly exceptional and unforgettable experience for each client I serve.
 
Additionally, most people’s homes are one of their biggest investments. Selling real estate is my full-time profession, which I take very seriously. When choosing an agent to sell your home, you should ask questions about your agent’s track record, past sales, and reputation to determine the dedication they will have to your listing and success in selling it for top dollar.

Testimonials

Ingrid

Ingrid

An Exceptional Realtor. Matt Winterle was an absolute pleasure to work with during the sale of our home. He was consistently calm and competent, using his extensive knowledge of the real estate market and current industry trend...
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Meghan L.

Meghan L.

Matt was wonderful to work with. Extremely professional and dedicated to successfully selling our home.
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Charles B.

Charles B.

Excellent experience with Matt and his team. This was a lengthy project that involved selling a complicated property and finding a suitable interim tenant to carry costs. There were many extra services and managerial tasks invo...
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Sandra K.

Sandra K.

Excellent and responsive, true partner in the sales process. Strengths in readying property for the market and a great marketing process!
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TLT Guest Houses

TLT Guest Houses

Matt did an outstanding job for us, and we couldn't be more pleased. From the first moment, Matt was extremely professional, providing us not only with a detailed plan on how to move forward with the sale but also with myriad a...
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Maggie O.

Maggie O.

So happy we chose to work with Matt when purchasing our home! Matt is professional, prompt to respond, and so knowledgeable about real estate. Something that sets Matt apart from the rest is his calm and relaxed demeanor. Purch...
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Seller

Seller

Matt and his team did an amazing job. We were particularly impressed with his attention to detail and willingness to help every step of the process. He made it easy for us during a stressful and hectic time. The help with stagi...
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Tim D.

Tim D.

Matt was an incredible partner throughout our buying process. He knows the South Shore market extremely well and made purchasing our first home a wonderful experience. Highly recommend Matt.
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Jessica S.

Jessica S.

I could not be happier with Matt and his team. This was my first time selling a home, and he walked me through what to expect while being there every step of the way. Even though I didn’t live nearby, Matt handled every task, b...
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David C.

David C.

We were not actively looking, but when the right home came up, we had to move quickly. Matt guided us through every step and made the entire process feel effortless. He was responsive, supportive, and always one step ahead, mak...
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Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact Matthew today to discuss all your real estate needs!

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