Agent Photo
Dana Whittaker
Legacy Properties Sotheby's International Realty
Legacy Properties Sotheby's International Realty home
Real Estate Agent

Dana Whittaker is a year-round Mainer and Senior Vice President at Legacy Properties Sotheby’s International Realty. She serves as the Director of Brokerage Services and Operations and spearheads company growth in the vibrant Maine real estate market. During her tenure since 2020, the company has expanded to six offices and over 100 dedicated agents, securing recognition as a Real Trends Top 500 brokerage in the US. Dana’s business development initiatives have been instrumental in consistently achieving nearly a billion dollars in annual sales.


Dana’s dedication to fostering agent success is evident in her innovative luxury real estate training workshops and materials, including a comprehensive Articulating Value bootcamp and specialized marketing brochures used companywide. Her expertise spans agent onboarding, strategic negotiations and best practices, and consulting with agents statewide to deliver exceptional results to the people they serve. She is also responsible for coordinating brokerage and community events and provides insightful broker support to agents, all while exemplifying a collaborative, results-driven culture.


Dana’s deep appreciation for Maine’s lifestyle fuels her love for cross-country skiing, paddleboarding, trail running, and walking the beach with her family and rescue dog. She enjoys savoring Maine’s local delicacies, whether it’s lobster rolls, oysters, or haddock tacos. After living in Ocean Park and Higgins Beach, she and her family now reside in Scarborough, staying close to their beloved summer roots and the coastal community that the Whittaker family has cherished for over a century.


Originally from San Diego, Dana holds a degree in English from San Diego State University. Before moving to Maine, she built a successful career in real estate, leading a top 1% team in Las Vegas with her husband and later leading Pacific Sotheby’s International Realty’s expansion in Coastal North San Diego. Her extensive experience includes opening new offices, coaching agents to deliver consistent value and expertise, and supporting growth in new markets. Dana also served on the NSDCAR Board of Directors and the Executive Board, earning recognition for industry leadership.


Her adventurous spirit has taken her around the globe, from Europe to Australia, and led her to conquer challenges like skydiving, swimming with dolphins, and walking on fire. Twice! Dana’s commitment to personal growth and leadership shines through in everything she does, including training and consulting productive and profitable agents and contributing to the focused and dynamic environment at Legacy Properties Sotheby’s International Realty.


Career Highlights:


  • Top 1% Las Vegas Team Leader
  • NV License (2000), NV Broker (2005), CA Broker (2011), ME Broker (2020)
  • Real Trends Top 500 Brokerage (2017-2024)
  • Former North San Diego County Association of Realtors Director & Executive Board Member
  • NSDCAR Political Action Delegate
  • 2019 Industry Leadership Award recipient


Workshops and Classes:


  • The Art of Real Estate Practice
  • Articulating Value
  • Luxury Marketing and Tracking for Sellers
  • Exclusive Buyer Representation in Maine
  • Advanced Communications and Negotiating
  • Career Visioning and Simple Business Planning
Designations: Broker

Dana Whittaker

  • Real Estate Professional
2 City Center
Portland, ME 04101
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