Distinguished by her deep understanding of neighborhoods, the broader community and the real estate business, Maria Milkova Gillette has served as the principal of real estate at Building the Bluegrass since co-founding the firm in 2019. In this capacity, she manages a team of 15 and oversees daily operations, with a flexible approach that adapts to the needs of both clients and agents. Ms. Milkova Gillette’s responsibilities include scheduling appointments, leading buyer and seller presentations, fielding calls from agents, handling contract-related inquiries, analyzing market conditions and conducting accountability calls to support quarterly business growth. She is dedicated to supporting newly licensed agents by offering continuing education and on-site training opportunities. In addition to her work with Building the Bluegrass, she has been affiliated with Bluegrass Real Producers since 2019, further expanding her influence within the industry.
Before founding Building the Bluegrass, Ms. Milkova Gillette worked as a licensed real estate adviser at Howard Real Estate, where she gained valuable experience navigating complex transactions across residential, commercial, farm and land development properties. From 2015 to 2018, she held the role of licensed real estate agent at The House Store Realty Group, during which time she also contributed to Andover Construction, building foundational knowledge in client representation and negotiation. Ms. Milkova Gillette’s earlier endeavors include such positions as project manager at Murphy+Graves+Trimble PLLC, realtor with Keller Williams Bluegrass Realty, licensed real estate salesperson at Douglas Elliman and associate project manager at Ricci Greene Associates. Her first professional experience was as an administrative assistant at Indiana University Southeast’s College of Business, Communication, and Technology from 2000 to 2002, immediately after she moved to the United States from her home country of Bulgaria.
Alongside her family history, Ms. Milkova Gillette’s educational background is rooted in Bulgaria. She obtained a technical diploma in building construction technology in 2000 from Hristo Botev Technical School, a high school in Sofia, Bulgaria, that specializes in preparing students for careers in construction and architecture. Subsequently, Ms. Milkova Gillette immigrated to the U.S. after her family won the green card lottery and studied graphic design at Indiana University Southeast for two years. After transferring schools and changing directions, she earned a Bachelor of Architecture from the University of Kentucky in 2006.
Throughout her professional journey, Ms. Milkova Gillette has received significant recognition for her achievements. Among the most notable, she was featured in the industry magazine Real Producers in 2025. Ms. Milkova Gillette credits her success to her parents, who instilled in her a strong work ethic and the belief that anything is possible through dedication and focus. She also acknowledges the mentors who guided her early career decisions and encouraged her transition into real estate during the financial crisis in New York City. Her commitment to ongoing professional development and ethical standards is showcased through her membership in Bluegrass Realtors and the National Association of Realtors since 2012, as well as her former membership in the American Institute of Architects.
In her personal life, Ms. Milkova Gillette is a devoted wife to her spouse, Michael, and a loving mother to two children, Sofia and Enzo. She finds balance through traveling and giving back to her community. Ms. Milkova Gillette has served as a big sister through the Big Brothers and Sisters of the Bluegrass since 2021 and volunteers with Habitat for Humanity International. She firmly believes that success is measured not only by financial gain but by building lasting relationships and living according to principles of kindness and generosity.
Looking ahead, Ms. Milkova Gillette plans to grow Building the Bluegrass organically through word-of-mouth referrals while also pursuing larger projects that benefit the community, such as initiatives that address housing shortages. She envisions acquiring land for new developments alongside various partners with potential expansion into commercial construction. Additionally, Ms. Milkova Gillette hopes to train more professionals who can work alongside her as she continues building a legacy within the industry. That legacy reflects resilience, adaptability and an unwavering commitment to serving others both professionally and personally.