More About Me

Anne Spry is a 30+ year real estate professional and has been Broker/Owner of Waterfield Sotheby’s International Realty for the past 11 years. With real estate sales consistently totaling $20 million or more per year, she works hard to ensure that each transaction, regardless of price, receives the utmost attention to detail.

A master negotiator who prides herself on her strong ethics and deep understanding of real estate in MA and NH, Anne invests time getting to know each and every one of her clients. Her extensive knowledge of staging, architecture, and overall value serves as a great asset, helping them achieve the highest value for their life’s investment.

Anne has always been a believer of excellence, equality, and, above all, achieving greatness. As a young woman, Anne served as the first female class president for the Boston Latin School’s class of 1981. She then attended Providence College where she founded an International Business volunteer program and started the Women’s Rugby Club. She also spent a year abroad in Fribourg, Switzerland.

A longtime resident of West Roxbury, when looking for a place to call home for her own family, Anne chose Winchester, where she has lived for the past 22 years. She is a lover of the outdoors, as well as an avid hiker and gardener, and values the time she spends in the Middlesex Fells Reservation with her husband Jim and two dogs, while she awaits the return of her now grown boys. Anne has developed many close friendships over the years. Her strong sense of community has inspired her to run seven Boston Marathons on behalf of friends through Dana Farber, as well as the local Glen Doherty Road Race held annually in Winchester. She is also a dedicated supporter of the Winchester Foundation for Educational Excellence (WFEE).


Anne did a great job marketing and selling our beloved home of 24 years. An antique house updated and full of charm but lacking some of the features of new construction, Anne knew that our home would not appeal to all buyers but would sing to the right buyers, she just had to find them. She was right! We were very, very happy with the process, the sale price, and steps toward closing. Most of all we were thrilled to know that our historic home was passing into the hands of a new family that would love and care for the property as we did. Anne's entire team were professional, responsive and unfailingly helpful and cheerful.

- Carol C.

Anne was a delight to work with. She met me spontaneously through the request of a friend and helped me bid on the house we saw that evening. Although that house fell through, we then embarked on a more traditional house hunt which resulted in a place I liked better, was less expensive, and ideally located. I would highly recommend her to anyone looking for an agent.

- Holly F

I am writing this review about Anne Spry, who brokered the purchase of our condominium. She was wonderful - knowledgeable, efficient, patient, supportive, informative and very reasonable and practical. She knew all the issues we were dealing with after 35 years in our raised-our-kids house. Although there were some complications regarding the seller, Anne navigated for us smoothly and competently. She always returned phone calls and texts and was totally available whenever. And she has a terrific sense of humor and positivity which is such a rare pleasure these days. I would recommend her without reservation.

- Phyllis Murphy, July 2019, Emailed by Client

Anne was very knowledgeable of the area and had us well prepared for the process of buying a home. She truly cared about us and always wanted what was best for us. She helped find the perfect home for us and we would definitely recommend.

- Shannon S

Anne helped us both purchase our new home and sell our existing home. She provided very good advice regarding the Winchester market, and the best timing and techniques of selling our home in general. Her advice helped us be very successful for both selling and buying. I would highly recommend Anne to others!

- Mike L