Anne Spry | Winchester Real Estate, Arlington Real Estate, Reading Real Estate, Woburn Real Estate

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 helped my fiancé and me buy our first home in our dream town. We knew nothing going into it and Anne helped guide us through the daunting process of buying a home. We are thrilled with the result and are so thankful to Anne for helping us.
Katherine and Paul B.
Anne is the best broker out there. Period. We were buying our first Home and she helped us through every process and made us feel comfortable. She always made us feel like we were her only clients we weren’t). I would recommend Anne to anyone.
Nick K.
We had an incredible buying opportunity and wanted to sell our home quickly. Anne and her team were absolutely fantastic in clearly setting expectations for the process, realistically guiding and assisting us in checking all the boxes to get the house ready to sell and expertly marketing and  showing the house and closing the deal. We were so impressed with her professional but incredibly friendly demeanor and we always felt like her most important client. Her team was full service - thinking about and helping with every detail, which was an invaluable stress reliever for a family that hadn't sold a home before. We can't recommend Anne enough!!!
Gregory B.
Anne’s expertise and experience were invaluable to getting my house sold quickly and easily. I’d recommend getting her involved early before it goes on the market so she can give you advice on what is worth fixing or updating to maximize your net profit.
Janet W.
Anne went above and beyond to help us purchase our forever home, which included a 2AM P&S signing, and extremely tight turnaround to close. We wouldn't think of ever using anyone else!
Mike L.
Working with Anne makes a very difficult process easy! The care and attention to detail was exceptional! We would highly recommend Anne and her team if you are considering buying or selling your home.
Patrick F.
With tremendous experience and intricate knowledge of the local markets, Anne was a pleasure to work with. Very aggressive in meeting relevant deadlines and making sure her clients' interests are a priority. Very happy to have worked with Anne.
Saurabh S.
My experience with Anne was very successful. I gave her a limited time frame to see my house and she moved quickly to get it photographed, create the marketing materials, and bring the house to market. After two open houses, she had multiple offers in hand and was instrumental in getting me the best possible outcome. I highly recommend her and her team for all the areas above.
Brenda R.
We had a wonderful experience both selling our old home and buying our new home. Anne’s insights and experience really made a difference. She guided us through the preparation of selling our home - which was extremely helpful. We sold in the first weekend. Anne was very patient and  knowledgeable in helping us find our lovely new home. Could not give a higher recommendation!
Tom B.

Anne is very professional and clearly knows how to handle high end properties. I have used her to sell one house, buy another and then sell that one. As my second house was a 2-family, she was able to provide me with quality tenants throughout my ownership. She is incredibly responsive and  listens to what I want while also educating me about the market. In each transaction, there were a couple of tricky points and Anne was able to negotiate them to my satisfaction.

Christine S.
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 M.
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.
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's International Realty without reservation.
Michael E.
From the moment I met Anne Spry she was highly professional in every aspect of the selling and buying process. She was super friendly and so easy to talk with. She is highly energetic and motivated to make sure the process runs as smoothly as possible. I would highly recommend Anne Spry in every  aspect of the real estate transaction process.
Maureen F.
Anne is outstanding! She helped us decide exactly when to put our house on the market, at what price we should list, and what repairs were necessary it so it would look its best. As a result of her guidance, our property sold in a single weekend over list with multiple offers. The proof is in the  pudding! Anne is extremely personable and fun to work with as well. We recommend her highly.
Elaine D.
Working with Anne Spry at Sotheby's exceeded our expectations. She provided us with volumes of market information to compare with and assist in finding a fair and competitive price to list our home. She worked around our very busy schedules and often through dinner and into the later hours of  the evening to assist us with completing paperwork and answering our many questions thoughtfully and thoroughly. Anne was very helpful in explaining the entire process for us since it had been a while since we had listed a home, and really relieved our stress level even though we were on a very tight time frame. Anne's market expertise helped tremendously in our home being sold in 9 days and over a school vacation week. In addition, Anne quickly helped us find an interim rental home for us to live in while our new home was under renovation. We couldn't have done it without her. We highly recommend Anne and her entire team, including Laura McCaughey and Renee Ryan, at Sotheby's for helping us through this process and cannot thank them enough
Kricket C.
Anne is a true professional. She is honest, trustworthy and knows her business. She sold our home in a weekend, and helped us buy our new home that we love!
Nancy P.
Anne Spry and her team handled everything in preparing our home for sale, during the on market process (open house), and then helping us prepare for the closing, keeping us on target including running the errands of picking up the final water bill, the original paperwork for the smoke  detectors/CO2. Anne and her team literally offer/perform the "one stop shop" attitude (they do it ALL). Anne and her team are there for you every step of the way, it was truly a stress free process for us in large part due to Anne Spry
Elizabeth P.
She was fantastic. Very responsive and knowledgeable. Provided excellent guidance and advice.
Anne Spry is amazing. She helped us buy our home and then sell it when we were transferred. She was knowledgeable, patient and endlessly helpful and supportive. She is a phenomenal agent. Nothing flustered Anne. She was quick to jump in and always there to help us.
Emily, Winchester
Anne Spry is knowledgeable, responsive and a savy business woman. Also professional & down to earth.
Anne, Needham
Our agent was invaluable throughout this entire process -- warm, flexible, knowledgeable, supportive, professional. I couldn't have asked for better experience. Thank you!
Dodie, Winchester
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.
Hope P.

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