Title
Dennis
Owned and operated by real estate lawyers that have a combined 100 years of experience, Sentinel Title & Trust o ers property owners, prospective buyers, and real estate professionals the services of a traditional title company with the added benefit of having knowledgable real estate lawyers on their side.
Leighann Triplett, Milestone Title Services
Preferred Partners
This section has been created to give you easier access when searching for a trusted real estate affiliate. Take a minute to familiarize yourself with the businesses sponsoring your magazine. These local businesses are proud to partner with you and make this magazine possible. Please support these businesses and thank them for supporting the REALTOR® community!
HANDYMAN SERVICES
Fix-it Flamingo (904) 474-1768 fixitflamingo.com
HOME BUILDER
Century Communities (904) 618-3220 centurycommunities.com
HOME BUYER
Mac Home Development Inc (904) 887-4015 machomedevelopment.com
HOME IMPROVEMENT
Design Works (941) 355-2703 hskindustries.com
HOME WARRANTY
Fidelity National Home Warranty
Trish Spivey (904) 716-0819 homewarranty.com
First American Home Warranty
Sierrah Stolte (904) 718-3685 firstamrealestate.com
INSPECTIONS
LunsPro Inspections (904) 249-6523 LunsProFlorida.com
River City Home Inspections (904) 654-4732 rivercityhomeinspect.com
INSURANCE
Kilpatrick Agency Inc:
Goosehead Insurance (904) 420-7711 goosehead.com/agents/ carol-kilpatrick/
MORTGAGE / LENDER
Atlantic Trust Mortgage (904) 338-9356
AtlanticTrustMortgage.com
First Coast Mortgage (703) 627-1775 FirstCoastMortgageFunding.com
Future Home Loans (904) 887-7926 future.loans
Movement Mortgage (404) 751-8463 tylertatum.com
North Florida Mortgage Brokers
Timothy Newman (904) 755-0307 northfloridamortgage brokers.com
Regions Bank - MacDonald Mortgage Team
Ian MacDonald (904) 998-4961 regions.com/mlo/ianmacdonald
OUTDOOR LIGHTING
JoyLights (904) 474-1768
WeBringTheJoy.com
PEST CONTROL SERVICES
Kingfish Pest Control (904) 595-5300 KingfishPest.com
PRIVATE SCHOOLS
Collage Day School (904) 900-1439 CollageDaySchool.org
REAL ESTATE MEDIA
Real Home Image
Michael Rowlette (904) 930-3756 realhomeimage.com
REAL ESTATE PHOTOGRAPHY
The Real Estateographers (904) 770-5262 therealestateographers.com
RENOVATIONS
Renovation Sells (904) 655-2411 renovationsells.com/jax
ROOFING & EXTERIORS
Mighty Dog RoofingJacksonville FLA (904) 867-7859 mightydogroofing.com
SPORTS TEAMS
Jacksonville Jaguars (904) 633-3348 Jaguars.com
TITLE COMPANY
Atlantic Coast Title & Escrow (904) 853-5591 atlanticcoasttitleandescrow.com
Cherry Tile LLC
Angelique “Chrissy” Kirsch (904) 300-3414 cherrytitle.us
Landmark Title (904) 367-2525 LandmarkTitle.com
Milestone Title Services (904) 716-7285 milestonetitlesvcs.com
Omega National Title Agency, LLC (904) 456-0858 Omeganationaltitle.com
Woods, Weidenmiller, Michetti & Rudnick, LLP
Josh Rudnick (239) 325-4070
WEALTH MANAGEMENT
Whitacre Wealth Management (410) 961-6548 WhitacreWealth Management.com
Chasing Big Goals: Why We Shouldn’t Settle for Less
BY: KRISTIN LUNSFORD
We are now in Quarter 2 of 2025! How are your goals coming along? Have you ever set an ambitious goal, only to second-guess yourself once you realize the effort it takes to achieve it? If so, you’re not alone.
I recently had a conversation with a middle school student who confidently told me he wanted to attend an SEC school for college. I commended his goal and assured him that I would support him in working toward it. To help him understand what it would take, I outlined the competitive nature of college admissions today. I mentioned some of the SEC schools he was interested in, sharing their acceptance rates, average GPAs, and test score expectations. As I spoke, I could see his enthusiasm begin to fade—his expression told me he was regretting sharing this goal with me and allowing me to help him.
The next time we discussed his goal, his mood was noticeably lighter. He had
done some research and found SEC schools with higher acceptance rates and lower admission requirements. I asked him if any of those schools were truly where he wanted to go. His answer? No. I then posed a tough question: Was he adjusting his goal because he was afraid of the hard work required to achieve it? He admitted that he was.
This conversation got me thinking—how often do we, as adults, do the same thing? We start off excited, setting goals that inspire and challenge us. But when we begin to grasp the level of effort required, self-doubt creeps in. Suddenly, the goal that once excited us now feels overwhelming. Instead of pushing forward, we adjust our expectations downward, making our goals easier to attain but ultimately less fulfilling.
Why do we let the fear of hard work and challenges stop us from pursuing what we truly want in life? Perhaps it’s because success requires discipline, resilience, and stepping outside of our
comfort zones. It’s much easier to settle for something more achievable than to persist in the face of obstacles. But if we keep adjusting our goals downward, we rob ourselves of the satisfaction that comes with real achievement.
Instead of backing down from challenges, let’s commit to pushing through them. When doubts arise, remind yourself why you set that goal in the first place. If it was worth aspiring to in the beginning, it’s still worth fighting for now. Success doesn’t come from choosing the easiest path—it comes from perseverance, dedication, and a willingness to embrace the effort required.
So, as we move further into 2025, take a moment to reassess your goals. Are you staying true to your ambitions, or have you started to lower the bar? If it’s the latter, challenge yourself to rise to the occasion. Your dreams are worth the effort—don’t let fear convince you otherwise.
GA while simultaneously working on her Master’s degree.
Her passion for working with children and her knack for communication served her well in her career teaching students with exceptional needs, both at the middle school and elementary levels. “All of the students I taught struggled academically, and one area I prided myself on in the classroom was teaching writing. I had many strategies and methods to help my students find a way to put their thoughts to paper, and that was always a very rewarding experience as a teacher.”
When a job opportunity became available for her husband Stephen in Jacksonville, the couple moved here in 2020, in the midst of the COVID-19 pandemic. Leighann started working at Milestone Title in August 2022 as marketing director in the Jacksonville office. Previously
she handled marketing for LunsPro Inspections.
You generally only need a title company when you buy, sell, or refinance, and most people use whomever their lender or agent recommends. Earning those recommendations requires steady relationship building and finding ways to go above and beyond to serve clients. This is a big driver for Leighann, and she knows it takes that kind of dedication to stand out in a market like Jacksonville.
One thing that sets Milestone apart as a title company is helping to pre-sign sellers. “We come to their house or their place of business before the closing, so they don’t have to come into the office. Because I’m also a notary public, I sometimes do those seller signings. It’s a service that some of our REALTOR® partners appreciate. Something else that I
When they grow, we grow, and that is the type of collaborative growth we strive for.”
can help them out with whenever they need it,” Leighann says.
Bloom Where You’re Planted Leighann and husband Stephen met in Georgia. They share a love of the Georgia Bulldogs (where he played baseball in 2002) and enjoy watching college football together.
The couple enjoy living in Nocatee with their two children, son Hudson, who turns thirteen in April, their seven-year-old daughter Claire, and their rescue dog Jax.
“Being in Nocatee, we love the golf cart lifestyle and enjoying the water parks, and we like going to the beach,” Leighann says.
“Our kids are very involved in sports. Hudson plays travel baseball and has for several years, and he recently started wrestling, so that’s a new adventure. Claire plays flag football, and between the two of them we stay busy with tournaments and practices.”
One thing Leighann really enjoys about the real estate market in this particular area of Florida is how Jacksonville seems like a big city with a small town vibe. It’s more about building personal connections and authentic relationships, and that has been a wonderful thing. I get to go out there and make friends.”
Recently Leighann and a group of “boss babe” friends graced the cover of St. Johns magazine as members of the “Secret Avocado Toast Society” sharing recommendations for their favorite local eateries.
Leighann very recently joined the board of Hugs St. John’s, a nonprofit that provides emergency food and clothes for students in need in St. John’s County. Among their many initiatives such as food and clothing drives,
each month the organization’s volunteers restock school-based food pantries at 20 St Johns County schools to help fight hunger among 1,000+ local kids.
“I am excited to serve on the HUGS board and utilize my connections in the community and experience in marketing to help them grow. HUGS provide an incredible service to children in St. Johns County who need it the most.” Leighann says.
Last year she also got involved with the TaxSlayer Gator Bowl, and she now serves on the Green Jacket Committee. “They have multiple charity ventures that they support and partner with, so that’s also been a great networking opportunity, because the TaxSlayer Gator Bowl attracts professionals from all different types of industries” she shares.
Connect with Leighann and learn more about how Milestone Title Services can assist you with your next project. The Jacksonville office is located at 12724 Gran Bay Parkway W, Suite 410, Jacksonville, Florida 32258. They can be reached by phone at (904) 716-7285 or email, paul@ milestonetitlesvcs.com.
Leighann and her husband, Stephen, have two children, Claire and Hudson.
Jena
Dennis
BY NICK INGRISANI
Born and raised in Jacksonville, Jena Dennis has always been deeply connected to the Northeast Florida area. After qualifying for early admission, she earned her associate’s degree while in high school and went on to earn three degrees in international business, cultural anthropology, and marketing from Florida State University.
“I felt like I branched out and explored what I wanted to do and where I wanted to be. I was passionate about the degrees I picked, they helped me broaden my horizons,” says Jena.
After graduating in the wake of 9/11, Jena initially planned to launch an importing company. However, recognizing the challenges of international business travel at that time, she pivoted and opened her first business — an antique store. Her new path turned into a long-term passion that progressed naturally into the world of estate sales and auctions. Over time, she expanded her
expertise, acquiring multiple business licenses and diversifying her portfolio.
Her introduction to real estate came through her husband, Allyn, a seasoned broker. Together, they merged their businesses, creating a firm that handles real estate transactions and specializes in estate sales, auctions, and business brokering. Their unique approach allows them to manage everything from selling homes and commercial properties to liquidating assets, making them a go-to resource for clients navigating complex transitions.
“Our motto is we can sell your home or business and everything in it. We work with a lot of attorneys and can do court-ordered sales, divorce settlements… I’ve literally sold everything that could be considered personal property and assets.”
Currently, Jena owns and operates a boutique brokerage with a team of 23
The great thing about loving what you do is you never feel like you need to retire. I’m very passionate about this work.”
PHOTOS BY THE REAL ESTATEOGRAPHERS
agents. Her expertise spans residential, commercial, and land sales, with a particular focus on historic properties in downtown St. Augustine and the revitalization of Hastings, Florida. Jena is the board chair for the Hastings Main Street non-profit, which is working to revitalize the community both historically and economically. Over the past two years, she and her husband have played a pivotal role in transforming Hastings’ Main Street, acquiring and renovating six buildings. What was once an area with 80% vacancy now boasts a 90% occupancy rate, thanks to both their efforts and community support.
“We’ve really turned the area around and have been getting a lot of grant funding — statewide and federal — to help rebuild the infrastructure of the community as well. It’s a super rewarding passion project.”
One of their most ambitious projects is the restoration of an 18,000-square-foot historic building, which they are converting into an event venue for weddings, corporate gatherings, and community functions. Beyond real estate transactions, Jena’s passion lies in preserving history and fostering economic growth within her community.
Her approach to real estate extends far beyond buying and selling homes. She is passionate about educating her clients on how real estate can be a vehicle for financial independence. Whether guiding a first-time buyer toward their dream home or helping an investor maximize
opportunities through tax strategies and portfolio diversification, Jena sees every transaction as a chance to empower her clients.
“Real estate can give you financial freedom through passive income that many people never even dreamed was possible. I have so many clients I initially help them buy a house, then we talk about investment properties. Whether it’s buying and flipping or renovating into a long-term hold, people can retire much earlier than they thought by diversifying their investments. It’s such a passion of mine to dramatically change people’s lives by helping them take advantage of the assets they have.”
One of the defining factors of Jena’s success is her breadth of knowledge and experience. Having navigated nearly every facet of the real estate industry — from sales and development to rezoning and asset liquidation — she brings a level of expertise that sets her apart.
“I’ve been through so many facets of this industry and all of that knowledge and experience elevates the services I can provide. I’m not here to just problemsolve and troubleshoot. I’m here to take it to another level and help each client excel and take advantage of opportunities within each transaction It’s a fun challenge to take something that seems like a normal transaction and elevate it.”
Outside of running her businesses, Jena prioritizes time with her family. She
and her husband, have three children, ages 11, 9, and 7, who are already learning the ins and outs of the family business. Integrating family into their entrepreneurial endeavors is a cornerstone of their values, ensuring that their children understand the importance of hard work and community involvement.
She also loves antiques, collecting jewelry and art, and crafting herbal tinctures and natural medicines. Her interests reflect a deep appreciation for history, craftsmanship, and holistic living, mirroring her approach to both business and life.
From building businesses to restoring communities, Jena’s impact is felt across multiple industries and throughout Northeast Florida. Her journey is a powerful example of how passion, adaptability, and a deep commitment to service can transform not just individual lives, but entire communities.
It’s a fun challenge to take something that seems like a normal transaction and elevate it.”
Jena and her husband, Allyn, have three children.
DEMI JUDD
BY JESS WELLAR
PHOTOS BY SHARLA HILL
FINDING THE ONE
When Demi Judd decides to host a client event, you know it’s going to be fun and fabulous.
A former wedding planner turned REALTOR® at REAL, Demi is hitting her stride while making plenty of true friends along the way. But she needed some convincing to take the initial leap.
“I really did not want to be a REALTOR® at first,” Demi admits. “They reminded me of car salesmen, not the vibe I want to give off. But then I kept thinking ‘What if I did it differently?’ I can ‘Dem-ify’ it by making it impactful, educational and fun.”
Foundation Of Faith
After high school, Demi pursued a degree in theology and Christian leadership from Chapel Bible College in California, with plans to work at her local Redeemer Church. While a position wasn’t open at the time, she still carries her faith with her on a daily basis; it’s firmly woven into every decision she makes.
“Rory Vaden put it so clearly — ‘God doesn’t care what you do, it’s how you do it’,” Demi shares. “That’s been a guiding principle for me. I’ve always wanted to lead in a way that honors God, and I strive to reflect that in my business.”
Demi then spent the next few years as a wedding planner, helping couples create magical memories.
“I loved being part of people’s stories,” she shares, but the high pressure of planning others’ big days became less appealing after her own wedding.
She shifted gears, taking a job at a local restaurant while mulling over her next move. A conversation with friends convinced her to explore real estate, and in August 2021, Demi went all in while keeping her expectations low.
“Real estate was a leap of faith,” she recalls. “But what started off as hoping it would work out went above my expectations. In every step of my career, I always remember to put my clients’ needs first, and that builds not only trust, but deep relationships.”
Bridal Expos And Back-toSchool Brunches When it comes to her business, Demi is always thinking outside the box. She’s cultivated a personal brand that’s authentic, relational, and downright fun — a combination that keeps clients coming back and referring friends.
What is your favorite place you have ever traveled and why?
Delaney Henderson Momentum Realty
My favorite place I’ve ever traveled to is Spain. It is by far the most beautiful country I’ve ever been to and the people are not only incredibly kind, but everywhere I went the locals were so happy and full of life. I truly cannot wait to go back this year and visit.
Michael Rowlette Real Home Image
My favorite place I have ever traveled is Breckenridge, Colorado. I go every year to snowboard and take in the mountain scenery. The combination of great snow, amazing views, and the laid-back yet vibrant atmosphere makes it the perfect place to unwind and recharge. Whether I’m on the slopes or enjoying everything Breck has to offer, it’s always a trip I look forward to.
My favorite place that I have traveled to is hands down Mykonos, Greece. The turquoise water, beautiful white buildings and delicious food. It’s magical and healing. I highly recommend it and can’t wait to go back
Coldwell Banker Vanguard Realty
Washington State, from Olympic National Park to Seattle to The Gorge Amphitheater. The state is beautiful with so many things to do and see.
Angela Gigi Urbanski
My favorite place I’ve ever traveled to is the Blue Ridge Mountains. We love exploring the various trails, especially the Appalachian Trail Legacy Loop, which is about five miles long and leads to the most majestic views. Standing at the top, it’s a powerful reminder that God is truly with us. Beyond the trails, we enjoy visiting the local vineyards like Buckley, Chateau Meichtry, and Roo. Each one is locally owned, crafting its own wines, and the combination of wine tasting, stunning mountain views, and the laid-back atmosphere makes for an incredible experience. We’re also fortunate that our Aunt has a beautiful cabin in the area, allowing us to visit often. There’s nothing better than waking up to watch the sunrise on the porch and ending the day with the peaceful sounds of nature as the sun sets. Every time we visit, it’s a peaceful reset — a chance to slow down, reconnect, and truly take in the beauty of the mountains.
Kaitlin Chernyshov
United Real Estate Gallery
The favorite place I’ve ever traveled to is Greece — from Athens to Santorini to Mykonos —every inch of it was absolutely breathtaking. The history in Athens, the stunning sunsets in Santorini, and the vibrant energy of Mykonos made it an unforgettable experience. Beyond the beautiful scenery, I loved immersing myself in the culture, the food, and the way of life that felt so different from what I’m used to in America. It was a trip that gave me a new perspective and memories I’ll cherish forever.
Christie Morgan
Better Homes & Gardens Lifestyles Realty
Munich, Germany — the culture, the history, the people, the food, the shopping, and the climate. We saw Eric Clapton in concert at the Munich Olympic Stadium.
Erica Harding
Engel & Völkers First Coast
My favorite place I’ve traveled so far is Paris, France! We flew to London for a Jaguar game and took the train over to Paris for the day. From the delicious cuisine, beautiful architecture and views and of course the amazing shopping... It was such a dream! I can’t wait to go back
Wendy Griffis
Better Homes & Gardens Lifestyles Realty
I keep going back to Hawaii. Perfect temperatures, lush green mountains, royal blue waters, flowers blooming everywhere, luxury accommodations, amazing food, coffee shops, and healthy eating. Also tons of outdoor hiking, sightseeing and water activities. Ahhh pure bliss!
Haley Sherman
Berkshire Hathaway HomeServices
Florida Network Realty
My favorite place I have ever traveled is Italy! The food, the people, and the history are all unforgettable! I highly recommend stopping by the Trevi Fountain in Rome and a day trip to Positano on the Amalfi Coast! It is truly magical!
Joy Doyle
Hover Girl Properties
For me, Israel, hands down. It makes the Bible go from black and white to full color.
Christine Hughes
Summer House Realty
My favorite place I’ve ever traveled to is Portugal. Its rich history, stunning landscapes, and vibrant culture make it an unforgettable destination. From the charming streets of Lisbon to the picturesque coastal towns of the Algarve and the breathtaking waves of Nazaré — Portugal offers a perfect blend of tradition and modernity, along with exceptional food and wine. What truly makes it special, though, are the warm and welcoming people who make you feel at home wherever you go. It’s a place that invites exploration and leaves you with lasting memories.
From the Desk of the President:
“Advancing
The Florida Economy: REALTOR® Advocacy at its Best”
BY TIM WEISHEYER, 2025 PRESIDENT OF FLORIDA REALTORS®
2025 is in full swing and the real estate market is holding strong. In January we saw a 3.5% increase in home sales, and we anticipate a slight dip in interest rates to keep adding to the market strength. As the economy and market continue to realign Florida REALTORS® is making sure our state economy remains strong as we work to help incentivize businesses to thrive and relocate to the Sunshine state.
One of the best ways to encourage businesses to relocate to Florida is to create a healthy economic environment. Due to the advocacy of Florida REALTORS® the business environment has continually improved in substantial ways in the last decade. One of the many examples is our work on the reduction, and ultimate elimination, of the business rent tax (sales tax on commercial leases).
In Florida, the “business rent tax” refers to the state sales tax on the rental, lease, or license to use commercial real property. Florida Realtors has successfully advocated for incremental reductions since 2017 and Florida businesses have realized significant savings as we have worked with the legislature and Governor’s office on this important initiative. Here’s a brief breakdown: Tax Rate Reduction:
• Originally a 6% sales tax on commercial lease and now down to 2.0% with more reductions on the horizon.
Estimated Savings:
• More than $2 billion in tax relief for businesses.
Impact:
• This reduction stimulates economic growth by lowering the financial burden on businesses.
• It’s make Florida more competitive in attracting new businesses and keeping existing businesses.
Businesses can reinvest the money saved into their companies, employees and new products, services and innovations.
The reduction of the business rent tax has provided substantial financial relief to Florida businesses - fostering a more favorable business environment, bolstering economic expansion and has freed up significant operating revenue to invest in Florida’s workforce. Beyond the aforementioned benefits, we know many of our members and brokerages lease commercial space for their real estate offices too. Florida REALTORS® and the Florida REALTORS® PAC have been championing this and many other legislative initiatives to protect our members and their businesses. Our work isn’t done and we are working to further reduce the business rent tax and provide more savings for you and your businesses.
We all know real estate is a vital part of the state’s economy and we are proud to be champions for it. Florida REALTORS® are zealous advocates for your profession because we know you depend on us and the Florida real estate industry represents 21% of the Florida Gross Product totaling more than 300 billion dollars.
The 2025 legislative session is ongoing, and we are proud to be in the halls of the state Capitol everyday working on your behalf. Florida REALTORS’® full advocacy agenda may be viewed at www.floridarealtors.org. We invite you to attend a recap session at our annual convention in Orlando on Monday August 25th -Friday August 29th. More information may be found at www. floridarealtors.org.
