

About Cher
Freeman’s ability to recruit and train technically and intellectually savvy real estate agents while fostering a positive corporate culture, is representative of RE/MAX SKY’s capacity to consistently deliver results to buyers, sellers, landlords, and all clientele. She understands what it takes in today’s market to ensure her agents’ success.
Freeman is also the CEO of SKY Development. SKY Development was founded in 2010 and successful produces “Thoughtful Development” residential projects throughout the Washington, D.C. area.
In addition to managing RE/MAX SKY, Freeman was appointed by District of Columbia Housing Finance Agency’s Executive Director to run the daily operations of the Agency’s HomeSaver $20 million program. Freeman spearheaded the US Treasury’s Hardest Hit Foreclosure Prevention Initiative. Freeman functioned as the internal point of contact for the various business partners and partnership organizations. She also oversaw and managed all marketing initiatives for the program. Freeman validated borrower eligibility and ensured quality control of all processes, while administering changes, updates or new mandates from Treasury and/or HUD.
From 2004-2014, Freeman managed the daily operations of her former brokerages, a residential and commercial real estate brokerage companies with over 55 agents and $50+ million in annual sales. She dedicated to the professional development of her agents, providing one-on-one mentoring and oversight. Freeman also contributed to the branding and marketing of the company, while building core business through residential & commercial clients and small- to mid-sized developers. Prior to this position, Freeman served as Director of Marketing for Advanced Communications Group from 2001 to 2004; and from 1999 to 2001, she built a solid network of contacts throughout Washington D.C. as the Press Secretary for Alcee Hastings, US House of Representatives.
As a native of Nicaragua her story is one of achievement, growth, and success. Freeman’s tenacity led her to become an expert in several key areas that have contributed to her current leadership position in real estate, including relationship building, business management, and effective negotiation. She is also multilingual and adept at communicating with diverse groups of people.
Freeman holds a Bachelor of Science in Broadcast Journalism from the University of Florida and is currently pursuing a Master’s in Business Administration from the University of Maryland. In addition to her commitment to lifelong learning, Freeman continues to be a champion of the arts and community. She is the creator of ART BUZZ, which is a joint fundraising event that assists aspiring, underprivileged young artists. She also volunteers at Martha’s Table, coordinating and participating in bi-annual trips to feed the hungry and homeless Miskito Indians on the Caribbean Coast of Nicaragua, Central America. Freeman serves on the Board of Delta Housing Board II of Delta Sigma Theta Sorority, Inc. as the Treasurer, and on the Board of DC Arts & Humanities Education Collaborative as a member. She is also the founder of www.AskCherado.com and the host of The AskCherado Radio Show on www.ListenVisionLive.com. Freeman is a 16 year resident of the District of Columbia and resides in Northeast, DC.
Transaction History
- 1 Year
- 2 Year
- 5 Year
Neighborhoods Cher Has the Most Experience In
Cher's Listings and Deals
Cher's Recent Active Listings
Awards and Designations
- Graduate REALTOR Institute
- Accredited Buyer Representative
- National Association of REALTORS
- Certified Luxury Home Marketing Specialist
- Broker Price Opinion Resource
Cher's Reviews
2/17/22Sheree Johnson
I enjoyed working with Cher and her team! Cher was very knowledgeable of home values and contract terms in the current Washington DC market. She was also very accessible and always addressed any questions or concerns I had with a timely response. Thanks to Cher I was able to purchase the perfect house for my family.
11/12/21Erica Meillier
Absolutely incredible experience with this entire team! Specific shoutouts to Cher Castillo and Lisa Coutts, literally could not have asked for more attentive, knowledgeable, and professional agents to work with. You guys were a huge blessing to us. Thank you for all of your help in finding our perfect Maryland home!!
9/21/21Teriauna Duran
Cher is a prominent and respected real estate guru in the DMV area. With all these accolades, you would never know because she is very professional, knowledgeable, responsive and informative. She made the process of selling and buying a home during the pandemic seamless. She and her team took pride in walking us through every step of the way. We advised and informed of every turn and detail and when things looked dire, she used her talent, expertise and resources to save the deal! She was truly on our side and we felt every bit of the pride she takes in providing exceptional customer service. I recommend Cher Castillo-Young for any and every real estate transaction.
