Cheryl Gillespie
REALTOR®
Real estate has been more than a career for me since 2011—it’s been a way to help people through some of life’s most meaningful transitions. As a Broker Associate and a consistently recognized top Realtor in Northeast Florida, I take pride in building lasting relationships and guiding my clients with honesty, care, and experience. As a native Floridian, I truly love the communities I serve. My family and I call this area home, and I’ve had the opportunity to both live in and own property throughout Duval, Clay, and St. Johns counties—from Fernandina Beach to South St. Augustine. That personal connection allows me to share not just market knowledge, but real insight into what makes each area special. I understand that buying or selling a home is deeply personal. My approach is to listen first, communicate clearly, and tailor each experience to my client’s unique goals. Whether you’re searching for your next home, selling a property, or exploring investment opportunities, I’m committed to making the process smooth, thoughtful, and successful. Helping my clients achieve their real estate goals isn’t just my objective—it’s what I genuinely enjoy doing every day.
200 Ponte Vedra Blvd | Ponte Vedra Beach, FL
904.338.8697
CHERYL’s Testimonials
“I am a 72 year old retired teacher. Cheryl is the most competent, diligent professional I have ever dealt with in ANY field of endeavor. I am not given to superlatives, but Cheryl could not be overrated. I’m sure there are many very good agents in NE Florida. I am also sure it would be a mistake not to be represented by Cheryl Gillespie if you have the opportunity to do.”
– Al Kramer
“From start to finish, Cheryl was flawless and extremely well organized in terms of cultivating a solid group of interested parties. When the right buyer was identified, she was on top of all aspects of the P&S until the deal was closed. It also occurred in a relatively short period of time. Great experience all around. Thank you Cheryl.”
– Mac Haskell
“Cheryl was highly recommended by friends when I started working with her in the summer of 2019. My plan was to take a look at a sampling of homes, go back home, and then buy in June, 2020. As we looked at homes during my initial visit, it became immediately obvious that Cheryl is an experienced professional with a vast knowledge of the area. She helped me narrow down my choices by listening to, as well as noticing, what I liked and disliked about each home we saw. From our first meeting to the final closing on the home, Cheryl was on top of every single detail. She sent me numerous links of homes to consider throughout the year, and frequently checked in with me to continue refining the search. Since I couldn’t be present because of COVID-19 restrictions, Cheryl showed me the finalist homes via video chat so I could see them for myself. From the moment I made an initial offer, Cheryl made the offer-to-closing process a breeze by letting me know what was needed every step of the way via email, text and numerous phone calls. She was a step ahead of everything that needed to be done. I am very happy with the home I chose, and delighted thatCheryl was by my side the entire time. Cheryl is experienced, knowledgeable and superbly organized. She knows how to listen and understand what a client wants and doesn’t want, and remembers the client’s preferences. She’s also very personable and cordial. I highly recommend Cheryl to anyone looking for an excellent real estate professional!”
– Clara Romeu
“Cheryl is great to work with. Took her time in assisting us. Thorough and always available when needed, quick to respond. Would highly recommend her. We are very happy with our home purchase.”
– John Meridith
“Cheryl’s hard work and expertise made our move from Minnesota to Florida a seamless transition! She is extremely organized, knowledgeable, and responsive. Not only was she “on point” during our process of finding and purchasing a home, she continues to be a great resource in helping us settle into our new community. Cheryl is a pleasure to work with and we would, without reservation, contact her in the future for any real estate needs.”
– Susan Romeu
“After we met Cheryl she: 1. Found us the condo we were looking for 2. Quickly negotiated a purchase price 3. Did research which convinced us to list our existing condo during the holiday season 4. Sold existing condo within 3 days of listing (during holiday season) 5. Provided tons of assistance during a sale and purchase process which was made more difficult by our residence in another state 6. Was always there to unlock a door or recommend a mortgage broker Could not be happier with her performance. She is more like a friend than a business acquaintance.”
– John Dickson
“Cheryl’s familiarity of Jacksonville and Saint Augustine served me very well as I was new to the area! She was extremely accommodating with my schedule. She did not push me in anyway but offered her valuable insights when I asked.? Cheryl is a top professional that addressed every detail along the way. I felt confident she was going to do anything to back me to get the property I wanted! I hit a home run with Cheryl!”
– The Levin Family
“I found Cheryl to be very professional; she did not waste my time, but was sensitive to my availability and time. Cheryl showed extensive knowledge of the property market; she was always very helpful and guided me through the whole process. I will definitely recommend her as a realtor and will make use of her expertise again.”
– The Wright Family
“Cheryl is a great realtor! She helped every step of the way in biting our first home. She showed us multiple properties and never got frustrated when we asked to see more. Once we choose a house – she was on top of it! We closed within the next month. She provided us guidance and the wisdom we lacked as first time home buyers. I was shocked how if we had questions or concerns late in the evening she would address them right away. We highly recommend Cheryl!”
– Suzanne Whelan