Windermere Homes & Estates Welcomes Cher Cunningham

Cher Cunningham, realtor with Windermere Homes & EstatesCher is a native Californian, growing up in the agricultural region of the San Joaquin Valley in Central California on an almond ranch in the country.  In the summer the kids spent the mornings working the ranch and numerous other agricultural jobs and then enjoyed the hot desert afternoons swimming in the river.


Parochial education until graduation and then college years were spent in Grand Rapids, MI at Calvin College.  Her first career was bartending at a dinner house, The Hungry Hunter in San Jose, living in the nearby mountain community of Los Gatos.  But every free moment was spent roaming and walking the beaches of Santa Cruz searching for shells during peaceful reflections and swimming the ocean.


A promotion moved Cher to Southern California to train in the management program.  Her next move was to Arizona to manage a newly built nightclub in Phoenix, AZ.  Real Estate was Cher’s next career choice as it fit her various interests in land, homes and providing service to people. She was licensed in 1980, starting in Residential Real Estate, then moving to a Real Estate Investment Firm in 1982 selling investment properties in the Pacific Northwest to California investors.


Craving a vacation in 1985, Cher concluded working in timeshare sales would provide the perfect mix of both travel and work. She moved to Mazatlán, Mexico, for her first timeshare position.  After returning to the States, she worked the next couple of years moving into management and then opened and developed the Resale department for a large Timeshare Developer in Southern California.  As Director of the Resale Division, the position proved an excellent fit and Cher enjoyed 27 years there while managing the resales of numerous timeshare properties.


A longtime member of St. Michael’s by the Sea in Carlsbad, and a proud supporter and volunteer for KPBS, Cher is also a member and supporter of the Encinitas YMCA where he swims laps and takes yoga classes. Ballroom and Latin dancing are just two of her passions, competing with her teacher and partner Daniel Vasco in the ProAm division.


After a hiatus spent traveling and marking items off her bucket list, such as working as a volunteer at the Riddles Elephant Preserve in Arkansas, Cher knew she wanted to return to residential Real Estate where she first started her Real Estate career.  Having lived in the village of Carlsbad for 17 years drew Cher to the  Carlsbad village Windermere office. I love the village and particularly bike riding along the ocean.


Clients say Cher is determined, focused, and hard working with a strong, impeccable service record coupled with integrity.


“We’d have to agree with her clients.  You don’t get much more tenacious and focused than Cher.  She has had such a wide range of experience, both internationally and here in the U.S., benefiting all kinds of client needs.  We believe in these gifts and feel fortunate to have her here in our Carlsbad Village office,” says Brian Gooding, co-owner of Windermere Homes & Estates.


To see what Cher’s up to next just give her a call at 760.473.2437, or via email at [email protected]


About Windermere Real Estate


Southern California-based Windermere Homes & Estates is the fastest growing real estate brokerage in California in 2015, according to industry magazine First Tuesday Journal. In just over 4 years, co-owners Rich Johnson and Brian Gooding have opened 19 offices and have had over 550 agents join their team. Their newest achievement, 2016 Brokerage Achievement of Excellence, was awarded to them by the San Diego Association of Realtors® (SDAR). Windermere Homes & Estates was honored to be the first recipient of the new annual SDAR Award given for standard of ethics, commitment to compliance and high regards for running their business.


Windermere Real Estate is ranked the largest regional real estate company in the Western U.S. with over 300 offices and 6,000 agents serving communities in Alaska, Arizona, California, Colorado, Hawaii, Idaho, Montana, Nevada, Oregon, Utah, Washington, and Mexico. Last year, Windermere closed over 86,000 sides for more than $31.7 billion in dollar volume. The Windermere family has a proud heritage of serving our neighbors via the Windermere Foundation which funds services for low-income and homeless families. Since 1989, the Windermere Foundation has contributed more than 35 million dollars towards improving lives in the communities where we live and work. For more information, visit