BROKER ASSOCIATE / REALTOR
#1 Top Overall Producer at Fannie Hillman + Associates in 2025, 2024, 2023 & 2021
Licensed Realtor since 2002 – Broker Associate since 2019
Meet MaryStuart Day, your unparalleled choice for luxury residential real estate in Winter Park, Maitland, Baldwin Park, Downtown Orlando, and surrounding areas. With an exceptional track record as the #1 Top Producing agent at Fannie Hillman + Associates, MaryStuart brings a wealth of expertise and insight to every transaction.
A native of Winter Park, MaryStuart possesses an intimate understanding of the area’s dynamic real estate landscape, enabling her to characterize market values with precision, street by street. Drawing from her background as a former Orange County Elementary Teacher, MaryStuart approaches real estate with a combination of warmth, compassion, and unwavering attention to detail.
With over 23 years of dedicated experience as a full-time Realtor, MaryStuart has remained a Top Producer, each and every year, at Fannie Hillman + Associates. MaryStuart does not measure her success by her sales volume or number of transactions; the highest achievement is in building trust with her clients and guiding them through one of life’s most significant financial decisions.
RECENT ACHIEVEMENTS I FANNIE HILLMAN + ASSOCIATES (FH+A)
- Named #1 Top Overall Sales Producer at FH+A in 2024, 2023 & 2021:
- Achieved a record-breaking $52++ Million in sales in 2021, setting the record for the highest annual sales volume by an individual or team at FH+A.
- Named #1 Individual Sales Producer at FH+A in 2024, 2023, 2021, 2017, and 2014-2012
- Triumphed over breast cancer, celebrating a cancer-free status in 2022!
NOTABLE NUMBERS & AWARDS
- $420+ Million: Total sales volume from 2002 to 2025
- $1.45 Million: Average sales price of homes sold in 2025
- Voted #1 Residential Real Estate (Individual Agent) in 2025 – Orlando Magazine, Home Design Award
- Ranked in the Top 50 out of 26,000+ Realtors (Top 0.1%) in Central Florida since 2021
- Ranked as of the “Hot 100” Realtors in Central Florida (out of 26,000+ Realtors) for the past 17 years – recognized by Orlando Magazine: 2008-2025
- Named one of the “Hot 100 Elite” by Orlando Magazine: 2020-2025
- The “Elite” distinction is designated to Realtors named on the Hot 100 list 5 or more times
- Awarded “5 Star Best in Client Satisfaction” – Orlando Homebuyer Magazine (2008-2021)
- Awarded “Five Star Professional’’ (10x winner)
- Awarded “Volunteer of the Year” & “Ambassador of the Year” by the Winter Park Chamber of Commerce in 2005 & 2006
SPECIALIZATIONS I WHEN “TOP-PERFORMING” MEETS “TAILORED EXPERIENCE”
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CERTIFICATIONS
- Licensed Real Estate Broker Associate (#BK3017236)
- Relocation Certified Specialist (RCS)
- RELO Certified Coordinator (RCC) & Relocation Director for Fannie Hillman + Associates (2001-2006)
COMMUNITY INVOLVEMENT
- Member of Orlando Regional Realtors Association (ORRA)
- Member of Florida Association of Realtors (FAR) & National Association of Realtors (NAR)
- Winter Park Chamber of Commerce Board Member from 2005-2007
- Leadership Winter Park Co-Chair of Class ‘14 (Graduate of Class ’13)
- Winter Park Chamber – Vice Chair Community Relations: 2006-2008
- Volunteer Chapter Advisor of the Chi-Omega Sorority at Rollins College in Winter Park
DAY FUN FACTS
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- Winter Park native – live here, work here…love it here!
- Winter Park High School alum & graduate of Chatham Hall Boarding School in Virginia
- Graduate of the University of Georgia (1997) – Go Dawgs!
- Orange County Public School Early-Childhood teacher from 1998 to 2002
- Awarded Teacher of the Year at Dream Lake Elementary School (2001)
- Favorite places: New Smyrna Beach in Volusia County, Boating on Lake Maitland, and any place my daughter is playing soccer or running track
























