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 - Partner

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

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 - Partner

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.

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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.

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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, she enjoys travelling near the ocean, and she is a wine and food enthusiast. Languages include English and Spanish.

Diane Chan

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

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

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

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

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

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

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. 

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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.

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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.

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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.