Top Producer

Anne Spry


48 Mount Vernon St., Ste. 1
Winchester, MA

Let this real estate agent know you found them on Boston magazine’s Find It Boston.

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Brokerage Firm:

Waterfield Sotheby's International Realty

Towns Served:

Winchester, Woburn, Stoneham, Medford, Arlington, Wilmington, Burlington, Lexington

What's your background, education and training?

I was born and raised in West Roxbury, and attended Boston Latin School where I served as the first female class president. I then attended Providence College where I founded an International Business volunteer program and started the Women’s Rugby Club and spent a year abroad in Fribourg, Switzerland. In 1989 I began my career in Real Estate, and I fell in love with the work. I moved to Winchester with my family in 1994, and opened the Waterfield Sotheby’s International Real Estate office in 2006.

What is your typical process for working with a new client?

Each client has their own needs and desires when purchasing or selling a home. I always try to find out what is motivating them, personally, to buy or sell and how they like to communicate so that I can do everything possible to achieve all or most of their goals.

What advice would you give a client looking to find a provider in your specialty?

This business is all about relationships, as buying and selling Real Estate can be a very emotional process. It’s very important to find an agent that you can form a good working relationship with and trust – someone who is reputable and can guide you through the process.  Ask your family and friends for recommendations – the best realtors will have plenty of people ready to recommend them.

What inspired your passion for your profession?

I enjoy the relationships and friendships that I build as I guide my clients through what can be an emotional, and sometimes tumultuous process. It’s incredibly fulfilling to see all the pieces of a transaction come together to form a complete, beautiful puzzle! I have a great work ethic and I strive for perfection.  It’s inspiring when clients choose to work with me again or refer me to their family and friends.

What services are you most excited to offer?

My clients benefit from top-quality marketing combined with the cohesive professionalism of our full-service local office, and my deep level of experience and strong negotiation. Our office works with the best photographers to show all our homes in their best light, and as an affiliate of Sotheby’s International Realty we have access to services such as RoOomy, who offer virtual staging, and the Curate app, which enables buyers to “stage” a property from their phone or device.

What is the best reaction you’ve ever received from a client?

The moment an offer is accepted is pure joy – truly an adrenaline rush! – for both buyers and sellers!

What makes your business stand apart?

I’m very proud that our office is comprised of a professional, ethical, cooperative team. We have fun together! We preview one another’s properties and are always willing to help one another. I’m also proud to be part of the Sotheby’s International Realty brand. Although a luxury brand, we sell distinction in all price ranges.  The brand is like a family, offering support to all affiliates large or small, and they are always first to market with new tools and technology to service our clients.

How many years have you been in business?

Just over 30 years - I started in real estate in 1989 and founded Waterfield Sotheby’s International Realty in August 2006.

What do clients have to say about you?

“Anne was amazing to work with! She went above and beyond to make sure we found the right house for us. As first time home buyers, she made sure we knew exactly what was going on and was there to answer any questions we had. We would highly recommend Anne!”


“I’m not sure where to begin. My family had a tricky situation and Anne was able to navigate it with knowledge poise and grace. She was compassionate and caring throughout the process. Without her recommendations we never would have been able to sell our parents’ home.”


“Anne is knowledgeable, personable and knows both her industry and catchment area well. She was terrific in creating a profile and advertising brochure for our home, as well as maintaining high standards in her showing of our property. Her persistence resulted in the efficient sale of our home in mid-January. Her attention to detail and the quality of her staff ensured not only our sale, but all the related details, including our move. We recommend her and Waterfield Sotheby International Realty without reservation.”

Any other information you’d like to provide – Hobbies, etc.

I enjoy giving back to my community! My office and I give a percentage of every home we sell to WFEE (Winchester Foundation for Educational Excellence) which supports the local public school system, and I am also an active member of the Rotary Club.  I have run seventeen marathons, run the local Glen Doherty Road Race, fundraised for Dana Farber Cancer Institute, and am an active Board Member for Camp Belknap in New Hampshire.  I’m close to reaching my goal of hiking up all of New Hampshire’s 48 4000-ft mountain peaks, and locally, I enjoy walking in the Fells with my husband and my dogs.



Top Producer: 2019