More About Me

Anne Spry is 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 of her clients well.  Her extensive knowledge of staging, architecture, and overall value serves as a great asset, helping her clients achieve the highest value for their life’s investment.

She brings more than 30 years’ experience to the community, offering long-standing relationships with brokers, attorneys, contractors, mortgage lenders and other professionals.  Anne’s strong trouble-shooting skills, natural ability to listen, desire to collaborate, and entrepreneurial spirit have come together in the real estate field.  She excels in helping buyers and sellers navigate the hurdles and details, so they make smart real estate decisions. With annual sales consistently totaling more than $27 million, she works hard to ensure that each transaction, regardless of price, receives the utmost attention to detail.

Seldom content with the status quo, the common thread in Anne’s resume has been identifying opportunity and taking action – in school sports, business and the community.

Anne was the first female class president at the prestigious Boston Latin School in 1981. While earning a bachelor’s degree in Economics at Providence College in 1985, Anne studied in Fribourg, Switzerland for one year. Some of Anne’s many other firsts include: starting an International Business Volunteer Program at Providence College (AIESEC); starting the Women’s Rugby Club at Providence College; obtaining a 6-month internship with Phillips Petroleum in Stavanger, Norway; and original member of the Winchester Highlander’s Running Club. In 2006, Anne created Waterfield Sotheby’s International Realty as a start-up and was the owner for 14 years.  She created a Business Partnership with WFEE (Winchester Foundation for Educational Excellence) who received approximately $70,000 to benefit education in Winchester.

A longtime resident of West Roxbury, Anne and her husband, Jim, chose Winchester to raise their family for the past 26 years. She is a lover of the outdoors, an avid hiker, 17-time former marathon runner and values the time she spends in the Middlesex Fells Reservation and Lake Winnipesaukee with her husband and dog. 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 a committed volunteer and community advocate, her endless enthusiasm and leadership has positively impacted the lives of many through her work with organizations such as: Board Member for Camp Belknap; Winchester Housing Partnership; ENKA Society; Host Family with A Better Chance (ABC); Winchester Schools; Boston Latin School; Winchester Rotary Club; and Business Ambassador to the (WFEE) Winchester Foundation for Educational Excellence.

Anne is excited to continue her life’s passion through your transaction!