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Meet The
Team

Meet The
Team
Gayle Winters
CEO | Team Leader | REALTOR® | CRS | Relocation Specialist
(617) 699-0310
Gayle@TheGayleWintersTeam.com
Licensing:9532093

As a premier Massachusetts Real Estate Agent ranking in the top 1% of all REALTORS® nationwide, Gayle is responsible for a wide range of duties on The Gayle Winters & Co. Team. She is an industry-leading real estate agent and a true professional, experienced specialist providing a comprehensive real estate experience for buyers, sellers, investors and builders. She has an awesome team of folks behind her that work closely together so they can provide nothing short of top notch service to all of her clients. Gayle has a very strong finance background with excellent negotiation skills, business planning, and seller/buyer/investor representation. With Gayle's previous experience as a Controller/CFO in finance, makes Gayle your trusted advisor!

Brittany Winters
REALTOR®
(781) 217-3426
brittany@TheGayleWintersTeam.com
Licensing:9581234

Brittany is a dedicated real estate professional who leverages her background as a special education teacher to provide an exceptional level of care and understanding to her clients. Her teaching experience equips her with the ability to break down complex concepts into clear, manageable steps, ensuring her clients feel confident and informed throughout the process. Passionate about working with first-time homebuyers, Brittany strives to make this milestone exciting and stress-free, offering empathy, patience, and unwavering support. She also has a deep interest in the intricacies of new construction, allowing her to provide valuable insights into design, craftsmanship, and energy efficiency for clients considering new builds. Combining compassion, expertise, and enthusiasm, Brittany empowers her clients to make informed decisions and feel supported every step of the way.

Dana Dunne
REALTOR®
(781) 653-6563
Dana@TheGayleWintersTeam.com
Licensing:9530621

Dana has joined the Gayle Winters & Co Team, bringing a wealth of experience and a passion for real estate. With a background in the biotech and fitness industries, she possesses a unique ability to understand the diverse needs of her clients and coach them to reach their goals. Turning her passion for interior design into a career, she has worked alongside top local agents, mastering the art of preparing listings for sale, creating perfect first impressions, and highlighting key features to make homes stand out. Now a full-time real estate agent with the Gayle Winters & Co team, she is dedicated to better serving her clients. She believes in the highest level of professionalism and honest communication, striving to make the home buying experience as stress-free and enjoyable as possible while advocating for her clients to receive the best insights and advice for their specific needs.

What Our Clients Have To Say

What Our Clients
Have To Say

Working with Brittany and Gayle was an absolute pleasure. From the very first meeting we knew we would be in good hands. They made sure we had realistic expectations but also worked hard to try and get us everything on our wishlist. This was our first home, and walking into the process was very daunting as we knew absolutely nothing about buying a home. However, they helped us through every step of the process, recommended contacts, and were available day and night to answer all of our questions. I would gladly recommend Brittany and Gayle to anyone I meet, and we are so excited to move into our first home!!

Gayle and Brittany are an amazing team that helped us buy the home of her dreams. Their real estate knowledge, professionalism, guidance, kindness showed through the entire home buying process. I'd highly recommend team Gayle Winters for your buying or selling needs. Thank you so much Gayle and Brittany! You are amazing!

Gayle and her team (Brittany) are top notch. Gayle is professional, knowledgeable, and provided us with the insights we were looking for (during walkthroughs- construction knowledge, potential for utility, etc.). She was always willing to answer any questions and provided us with resources and a network of people during our home search (and beyond). Gayle has an extensive network and is always willing to make suggestions when asked but was never pushy or overwhelming. She is friendly and lovely to work with. The Gayle Winters team is there to support you and provide the best possible experience. Whether you're buying or selling, I would highly recommend them!!

We had a great experience with Gayle! She is extremely knowledgeable and helped us navigate our first home purchase. She took the time to answer all our questions, never rushing us, and made sure we were comfortable throughout the process. She was an incredibly valuable resource in walk-throughs, pointing out things we would not have otherwise noticed, and she provided excellent advice on pricing. Gayle is also very well connected in the area and helped us find various service providers, all of whom we were happy with.

Gayle and her team help us to get this house in Lexington, MA. She has given us very useful information and her knowledge in the area help us a lot. She is professional and always here to help. Thank you!

As first-time homebuyers, we couldn’t have asked for a better guide than Brittany Winters. She, and Gayle Winters, were crucial in helping us navigate the complexities of the process, from finding a solid, livable home we could make our own, to mediating negotiations with the seller’s agent. Her knowledge of the greater Boston market and support during our mortgage search were invaluable.

We worked with Brittany and she was fantastic! Brittany was very professional yet also very personable and friendly. She kept us informed throughout the process of buying our first home which spanned almost a year. We did most of our home search from across the country but whenever we made a visit to MA she was so accommodating and kept in touch even when we were across the country.

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MEET OUR TEAM

What Our Clients Say

Working with Brittany and Gayle was an absolute pleasure.

Working with Brittany and Gayle was an absolute pleasure. From the very first meeting we knew we would be in good hands. They made sure we had realistic expectations but also worked hard to try and get us everything on our wishlist. This was our ...

Sakara Perry

Gayle and Brittany are an amazing team that helped us buy the home of her dreams.

Gayle and Brittany are an amazing team that helped us buy the home of her dreams. Their real estate knowledge, professionalism, guidance, kindness showed through the entire home buying process. I'd highly recommend team Gayle Winters for your buying ...

Paramjit Singh

Gayle and her team (Brittany) are top notch.

Gayle and her team (Brittany) are top notch. Gayle is professional, knowledgeable, and provided us with the insights we were looking for (during walkthroughs- construction knowledge, potential for utility, etc.). She was always willing to answer any ...

Katerina Leventis

We had a great experience with Gayle! She is extremely knowledgeable and helped us navigate our first home purchase.

We had a great experience with Gayle! She is extremely knowledgeable and helped us navigate our first home purchase. She took the time to answer all our questions, never rushing us, and made sure we were comfortable throughout the process. She was ...

Liz Enlow

Gayle and her team help us to get this house in Lexington, MA.

Gayle and her team help us to get this house in Lexington, MA. She has given us very useful information and her knowledge in the area help us a lot. She is professional and always here to help. Thank you!

MW Professional Engineering PC

As first-time homebuyers, we couldn’t have asked for a better guide than Brittany Winters.

As first-time homebuyers, we couldn’t have asked for a better guide than Brittany Winters. She, and Gayle Winters, were crucial in helping us navigate the complexities of the process, from finding a solid, livable home we could make our own, to ...

Katherine López

We worked with Brittany and she was fantastic!

We worked with Brittany and she was fantastic! Brittany was very professional yet also very personable and friendly. She kept us informed throughout the process of buying our first home which spanned almost a year. We did most of our home search ...

Nicole Dilger

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