Milena Simsic is a Windsor-based entrepreneur, real estate investor, and founder of three distinct companies: WindSocial Realty, Windsor REI Social, and Windsor Real Estate Insider Magazine.

Born to Yugoslav immigrant parents, Milena did not grow up with wealth or a family foothold in business. What she had was a clear-eyed plan. She trained as an intensive care nurse, crossed the border to Detroit for work, and used every dollar of that income to quietly build a real estate portfolio in Windsor. By 25, she owned 8 rental units, had accumulated a net worth of $1 million, and had replaced her nursing income entirely through cash flow. At 26, she walked away from clinical practice to build something she could own.

Today, Milena leads WindSocial Realty, her real estate team operating out of Walkerville in Windsor, Ontario. She founded Windsor REI Social, now the largest real estate investor networking event in Windsor, with over 3,000 members. Her publication, Windsor Real Estate Insider Magazine, is the only neighborhood-by-neighborhood data resource of its kind in the city, tracking average home prices and over-list performance across Windsor’s distinct markets, with more than 8,000 subscribers. Her combined social media following exceeds 31,000 across Instagram and TikTok.

For over a decade, beginning in her university years with Enactus, Milena has been teaching young people how to build businesses. That work now lives inside the YETI program, where she translates her direct experience as a first-generation entrepreneur into frameworks that students and emerging founders can actually use. Her mentees are not hypothetical success stories. Many of them now own and operate their own businesses. Others have become clients of hers, a full-circle outcome that reflects the depth and durability of what she teaches.