Opening doors for changing lives.
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. 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.
JUDY BLACK
BROKER | PARTNER
407.810.1803
Originally from Buffalo, New York, Judy graduated from the University of Florida and served in the United States Air Force. She has been a top performing real estate agent since 1977. In her spare time, she enjoys traveling and spending time with her grandchildren.
SARAH CARLSON
PARTNER
407.579.8935
Originally from Buffalo, New York, Sarah received her undergraduate degree from the University of Florida and her MBA from Rollins College. 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.
JASON BLACK
MANAGING PARTNER
407.497.6345
Originally from Orlando, Florida, Jason is a graduate of Cornell University and the University of Florida Law School. He has been a top performing real estate agent since 2001. In his spare time, he enjoys music, writing and playing soccer with his boys.
AMANDA BLACK
PARTNER
407.616.0140
A native of Windermere, Florida, Amanda graduated from the University of Alabama and Seminole State College with bachelor's and specialist degrees in telecommunications and film, and interior design. She has been a top performing real estate agent since 2008. In her spare time, she enjoys boating on the Butler chain, pilates, and beach days with her daughter.
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, she 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, Wisconsin, and has been a top performing real estate agent since 1989. In her spare time, she enjoys travel, tennis, snow skiing, and music.
KAREN JORGENSEN
ASSOCIATE
407.808.3118
Originally from Roanoke, Virginia, Karen graduated from East Carolina University and received her Masters in English from the University 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.
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 custom pet tree houses.
DEEDEE SHERMAN
ASSOCIATE
321.663.5106
Originally from North Carolina, Deedee graduated from the University 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.
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.
ANN WARGO
ASSOCIATE
407.616.3041
Originally from Erie, Pennsylvania, 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.
JANEIL JORGENSEN
ASSOCIATE
407.455.3210
Originally from Utah, JaNeil has been a top performing real estate agent since 2013. In her spare time, she enjoys photography and rollerblading.
CONNIE COLLIER
ASSOCIATE
407.448.2292
Originally from Sioux Falls, South Dakota, Connie has been a top performing real estate agent in Central Florida since 1998, working for a number of leading home builders before joining UPSIDE in 2021. In her spare time, she enjoys snow skiing, traveling, and relaxing at the beach with family.
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TERRY ANDERSON
ASSOCIATE
407.760.0468
Originally from Littlefield, Texas, Terry graduated with a finance degree from the University of Central Florida before earning her Florida real estate license in 2012. In her spare time, she enjoys travel, home design and reading.
KATHIA RODRIGUES
ASSOCIATE
321.217.5707
Originally from Sao Luis, Brazil, Kathia earned her Masters in Education from the Federal University of Piauí and continued her studies at the University of Central Florida. She has been a top performing real estate agent since 2018. In her spare time, she enjoys reading, biking, and cooking. Languages include English, Portuguese, and Spanish.
JULIE PICKREN
ASSOCIATE
904.553.8031
Originally from New Jersey, Julie earned degrees from the UNC Greensboro and University of St. Francis before starting her real estate career in Florida with a heart for helping clients in the 55+ market. In her spare time, she enjoys reading, traveling, and spending time with grandkids, and volunteering in local elementary schools.