Zach DiFilippo
St. Augustine, Florida
- Certified Luxury Property Specialist
- Top Producer in St. Augustine
- Flagler College Alum
- St. Augustine Local
- Career Production - Over $90,000,000 with over 200 closed transactions
As a Flagler College alum with a Business degree and a Finance minor, I’ve built my career on the values of hard work, trust, and active listening. Having grown up around the business with my dad, Rich DiFilippo, working in real estate for 30+ years in Ocean City, Maryland, I developed an early appreciation for what it takes to serve clients with integrity and care.
Since beginning my own real estate career in 2017, I’ve focused on helping people navigate the Northeast Florida market through professionalism, communication, and genuine connection. I maintain a strict 24-hour response policy and pride myself on being accessible so we can make every transaction seamless.
Living on Anastasia Island, I enjoy the same coastal lifestyle I help others discover—whether it’s live music, surfing, Brazilian Jiu-Jitsu, or local events that bring the community together. Outside of real estate, the most important thing to me is spending time with my wife, Maddie (who works alongside me as Head of Marketing and Operations), and our dog, Bruce Almighty.
Our goal is simple: to combine experience and local insight so you feel confident and comfortable with your next big investment!
Hear from some of my satisfied customers
Posted on Stephen BorgesVerified Working with Zach was hands down the best real estate experience I’ve ever had. From our first conversation to closing day, he was professional, knowledgeable, and genuinely committed to helping me reach my goals. He took the time to understand what I was looking for, gave honest advice, and handled every detail with precision. What truly sets Zach apart is their communication—always prompt, clear, and reassuring. Whether it was navigating offers, scheduling showings, or answering last-minute questions, they were there every step of the way. Their local market knowledge and negotiation skills were a huge asset. If you’re looking for someone who goes above and beyond, look no further. I couldn’t be happier with my home purchase, and I’d recommend Zach to anyone in a heartbeat.Posted on Thomas SaundersVerified Zach Difilippo was really easy to work with and made our buying process feel like a piece of cake! Zach was absolutely incredible answering all of our many questions and texts. He treated us like we were a family member and went above and beyond for us in this purchase. I hope this is our forever home and we won't need a realtor again, but if we do we will absolutely be a returning customer! The SaundersPosted on Rob JennisVerified Zach was extremely knowledgeable about the area and was very efficient in finding homes that were in our price range. Zach did a great job negotiating the sale and helped with the closing as well. We would definitely use him again.Posted on John WalkerVerified Zach was wonderful to work with during our relocation to St Augustine. We moved from out of state so his attention to detail was very important. He listened carefully to our requests and delivered with great results. Zach was very personable and made us feel like we were his most important client. Zach knows the area well and has a vast network of people in many trades that can assist if needed. I highly recommend Zach for your real estate needs.Posted on Eli J RemingtonVerified Zach was amazing! He was always available and helped us so much even though we were 1,000 miles away. He went and did walk-thru videos of the homes we were interested in, he went to bat for us when one home inspection did not go well. Can’t say enough about all of the help he provided!Posted on lindseywalker126Verified Zach was incredibly helpful and knowledgable throughout the entire process. We were buying out of state and relied on him heavily to be our eyes and ears while our house was being built. From our initial meeting until closing, we had full confidence and peace of mind in his guidance. We can't recommend Zach enough!Posted on George StefanouVerified Zach was fantastic. Helped us every step of the way. We were buying from out of town and he would offer to be our eyes and ears on the ground going video walk throughs and making himself available at all times. He also kept his ear to the ground. He knew we fell in love with a home that sold in 4 hours to another buyer but he kept in contact with the listing agent for us and before the new home even went back on the market he knew kept us in the loop and helped us close a fantastic deal. Can’t Zach enough for all his help and care along the way.Posted on Justin ArmstrongVerified Zach helped my wife and I find our dream home in NE Florida. He made the home buying process feel like a breeze while navigating a competitive NE Florida market. We have so many nice things to say about Zach, but it was his positivity and professionalism that stood out the most. He went above and beyond to help us and has played a large role in forever improving our quality of life. I highly recommend giving Zach a call with any of your real estate needs!Posted on CaseyJones66Verified Zach possesses an extensive knowledge of the St. Augustine real estate market, providing invaluable insights and guidance throughout the entire process. He listened attentively to my preferences and requirements, ensuring that the properties he showed me aligned perfectly with my needs. His attention to detail and thoroughness in researching each listing was truly impressive. He made the process of being a First Time Homebuyer a breeze!Posted on kgwilkinsonVerified We were so fortunate to find Zach as we looked for a home in the St Augustine area. Right from our first meeting Zach was professional, prompt and responsive to all our many questions. He helped immensely as we navigated the finding then buying process. He made it easy and enjoyable every step of the way. Do yourself a favor and contact Zach now to make your journey smooth and pleasant. Thanks Zach!Load more





