Above, Jared Oliver
Like most experienced residential real estate professionals, Jared Oliver knows his territory as well as—or better than—everyone. While he was surprised to learn that Zillow recently tabbed his core area, Jacksonville, Florida, as the best market for first-time buyers this spring, he certainly knew why.
“It’s easily a third of the buyers we work with,” he says. “One out of every three buyers is either a first-time buyer or they’ve been renting for quite a while. We’re running into people who are first-time buyers who are in their 60s, which is very specific to the Florida market.”
Oliver is a team leader with ChuckTown Homes, a real estate group with LPT Realty headquartered in Charleston, South Carolina. Founded in 2006, it has grown to about 200 agents and operates in seven markets across the Southeast, including Jacksonville.
ChuckTown works closely with Zillow to connect buyers and sellers, with a strategic focus on tailored support, down payment assistance and products optimized for older clients.
Jacksonville’s “First Coast” location and its more Georgia-like feel mean many out-of-state buyers bypass it for areas farther south, reducing competition for local first-time buyers who are not directly battling the broader migration into Florida. In this environment, lower competition becomes the key advantage: fewer multiple-offer situations allow first-time buyers using FHA, USDA and down payment assistance to compete successfully, unlike in hotter markets where cash and over-asking bids dominate.
“Jacksonville is a collection of a lot of really large, really well established neighborhoods, but the average price point is always going to hover between $300,000 and $450,000,” says Oliver. “So for the first-time buyer who can’t afford that multi-million-dollar downtown condo, there’s a lot more to choose from.”
A former sheriff’s deputy who transitioned into real estate about seven years ago, Oliver, 35, emphasizes expectation-setting, trust-building and “win-win” negotiation as core to serving first-time buyers. He describes a deliberate process: clearly outlining roles and next steps, giving buyers a “playbook” for the search and reframing early showings as opportunities to learn preferences rather than pressure-filled decision points. He sees confusion as a lack of clarity and positions his role as protecting clients’ positive emotions by absorbing stress and ensuring they never feel forced into a decision that isn’t in their best interest.
“After graduating college, I went into law enforcement and was a deputy between 23 and 29,” says Oliver. “When I got out of law enforcement, I got a real estate license because there’s a lot of overlap between the professions. I found that people skills, building rapport very quickly with people you’ve never met before and establishing a level of trust are all necessary.”
Nearly half of Jacksonville’s active listings are affordable, according to Oliver, compared with a countrywide inventory level around 20%.
“The biggest thing here is an opportunity buyers have getting sellers to work with them as opposed to against them,” he says. “The goal is not to bully sellers. It’s to strive for a win-win, coming to terms that work for everybody, getting a seller their number while also giving the buyer the assistance they need.”
Zillow Showcase, explains Oliver, provides further support by giving out-of-state and hesitant buyers detailed 3D walkthroughs and floor plans that reduce uncertainty and make them more comfortable engaging, often leading to targeted questions about room sizes and virtual confirmations rather than basic discovery. At the same time, he notes that modern buyers often arrive knowing extensive listing details from online research, shifting the agent’s value toward strategy, market insight and negotiation rather than basic information.
“We use Zillow Showcase as a tool that we pitch to sellers, and it absolutely helps sell their homes quicker and for more,” he says. “It has helped as a rule across the board bring more clarity to what the home offers and what it doesn’t, which creates comfortability that allows us to have a more organic conversation instead of it being so intimidating.”
Managing buyer and seller expectations
Oliver asserts that the conversation about setting expectations is huge, “because there’s a metric out there that 5% of people will buy the very first home that we meet them at, which is wild to think about, right? I just met you and then an hour later, I may potentially be helping you spend hundreds of thousands of dollars. Earning trust is paramount. When we meet buyers who are effectively strangers, setting expectations is important—a deliberate part of the process which I don’t neglect or ignore.“I make sure I explain explicitly what they can expect from me, what I should expect from them,” he continues. “I’ll take time to answer questions and walk through any scenario that’s important to them because people just want to feel heard. Confusion is typically a lack of clarity, so I want to make sure I bring them that clarity and know that they feel heard and listened to and confident that no matter what, they’ll never be put in a position where they feel like they’re being forced to make a decision that’s not best for them and their family.”
For sellers, Oliver argues that “turnkey is everything” in the current environment. Even in good neighborhoods at solid price points, homes need strong presentation—fresh paint, lawn care and resolved deferred maintenance—to ensure buyers fall in love online before they ever visit in person. He encourages agents in other markets to deepen their negotiation skills, think creatively about terms beyond price and move beyond the pandemic-era habit of simply advising buyers to offer over list, especially now that many Jacksonville sellers must accept that they will not achieve peak-pandemic pricing.
Making the numbers work
Oliver points out that Zillow data shows that affordability is improved, and draws a correlation regarding interest rates.
“The first point I make with buyers is to say, ‘look, I don’t have a crystal ball. I can’t predict the future. I don’t know where interest rates are going or what the Fed’s going to do,’” he says. “Instead, I typically advise buyers to focus on how the home purchase helps achieve their current goals. Is the interest rate offered something that works against you or something that we can try to work with?
“I take pride in being able to come up with a credit solution that works for the buyer and the seller, to get the seller what they’re looking for but also make the terms for the buyer work in their favor. Affordability is tied to what the buyer believes is the limit for their mortgage payment. I try to negotiate so the seller gets what they’re looking for, and then use a credit for the buyer to help buy down their rate and get a mortgage payment that makes sense to them.”
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