Careers

Interested in joining our team?  

Our globally recognized brand with a reputation for excellence inspires a highly collaborative team full of passion, motivation and energy.  Based in the heart of Winchester, our recently renovated office offers a private, flexible workspace to meet clients and connect with other brokers.  Our full time marketing team and a dedicated office manager support our agents to successfully balance their home and work lives. Our knowledge of the communities we serve is unrivaled, and we support many events, charities and foundations in our local area.

Echoing our brand reputation for art, luxury and quality our agents are encouraged to be creative with their marketing, using high quality photography to produce stunning marketing materials that really sell our homes.   We are also proud to be at the forefront of developing new technology to ensure our agents can reach their full potential. Check out Curate by Sotheby’s International Realty, the first real estate brand app to utilize augmented reality staging, or our award-winning YouTube channel, the only real estate channel with over 170,000 subscribers, showcasing property videos to a worldwide audience.

Join us. Contact Anne Spry for a confidential conversation.

Independently owned and operated for 13 years in Winchester, we are a highly collaborative office of over 20 active agents (and growing), with a dedicated Marketing Team  and Transaction Manager supporting our agents. We have strong connections with buyers and brokers within the Boston Metro North region, and also through the Sotheby's International Realty brand. We are proud to support our communities through sponsorship of events and donations to local charities, foundations, and sports teams. A percentage of every sale made through our office goes to the Winchester Foundation for Educational Excellence (WFEE).

Waterfield Classic Homes, LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act.

Sotheby's International Realty® is a registered trademark licensed to Waterfield Classic Homes, LLC.
Each Sotheby's International Realty® office is independently owned and operated.

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