Welcome to the UPSIDE!

In 1985, Judy Black opened her first real estate office in Windermere, Florida, calling it Main Street, REALTORS. Known for lakefront listings, a service-first mindset, and elevated professionalism, the company grew to 4 traditional offices and 120 talented professionals, selling close to 10,000 properties over 28 years. 

In 2019, Judy and company opened UPSIDE Real Estate by reimagining the modern real estate office for accomplished real estate agents looking to join forces and break the mold. UPSIDE may be introducing a fresh take on our profession, but it was born from a familiar mission...

To open doors and help change the lives of the neighbors we serve!

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JASON BLACK

Partner

407.497.6345

Originally from Orlando, Jason is a graduate of Cornell University and Florida Law School, and a top performing real estate agent since 2001. In his spare time, he enjoys music, writing and playing soccer with his boys.

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JANE DUNKELBERGER

Associate

407.913.6776

A Florida native, Jane graduated from Tallahassee Community College and has been a top performing real estate agent since 2013. In her spare time, Jane enjoys travelling near the ocean, and she is a wine and food enthusiast. Languages include English and Spanish.

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DIANE CHAN

Associate

407.929.2128

Originally from Trinidad, Diane attended the Layton School of Art in Milwaukee and has been a top performing real estate agent since 1989. In her spare time, she enjoys travel, tennis, snow skiing, and music.

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JOE DELROCCO

Associate

407.788.4426

Originally from New Jersey, Joe grew up in Lake Mary, Florida and has been a top performing real estate agent since 1989. In his spare time, he enjoys gardening, hiking, biking, and building elaborate tree houses for pets.

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MAUREEN COONROD

Associate

321.945.9440

Originally from the United Kingdom, Maureen is a former London police officer and has been a top performing real estate agent since 2004. In her spare time, she enjoys travel, art, writing and country music. Languages include English and French.

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ANN WARGO

Associate

407.616.3041

Originally from Erie, PA, Ann graduated from Gannon University and has been a top performing real estate agent since 2000. In her spare time, she enjoys helping others and giving back to her community.

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JANEIL JORGENSEN

Associate

407.455.3210

Originally from Utah, JaNeil has been a top performing real estate agent in Florida since 2013. In her spare time, she enjoys photography and rollerblading. 

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SARAH CARLSON

Partner

407.579.8935

Originally from Buffalo, NY, Sarah received her undergraduate degree from the U. of Florida and her MBA from Rollins College, and she has been a top performing real estate agent since 2002. In her spare time, she enjoys reading, theater, going to the beach and spending time with family.

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JUDY BLACK

Partner

407.810.1803

Originally from Buffalo, NY, Judy graduated from the U. of Florida, served in the U.S. Air Force, and has been a top performing real estate agent since 1977. In her spare time, she enjoys traveling and spending time with her grandchildren.

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KAREN JORGENSEN

Associate

407.808.3118

Originally from Roanoke, VA, Karen graduated from East Carolina U. and received her Masters in English from the U. of Texas - Pan American. She has been a top performing real estate agent since 1998. In her spare time, she enjoys water skiing, writing novels, painting and piano.

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DEEDEE SHERMAN

Associate

321.663.5106

Originally from North Carolina, Deedee graduated from the U. of North Carolina School of the Arts and has been a top performing real estate agent since 2012. In her spare time, she enjoys yoga, ballet, photography and gardening.

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DOUG TROVILLION

Associate

321.229.2585

Originally from Winter Park, Doug graduated from the U. of Florida School of Building Construction and has been a top performing real estate agent since 2018.

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BARBARA METALLO

Associate

407.496.4272

Originally from San Diego, Barbara graduated from Grossmont College and has been a top performing real estate agent since 1998. In her spare time, she enjoys spending time with her family.

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