Biggest Opportunities For Real Estate Investing Are Uncovered In Downtown Jacksonville


In this episode of the Not Your Average Investor Show, we speak with Alex Sifakis, the Co-Founder and President of JWB. He shares his vision of how Downtown Jacksonville will increase real estate investing opportunities and boost Jacksonville, FL real estate property values. This is good news for JWB's clients and potential investors who want to grow their investment property cash flow in this sizzling hot real estate market.

What Is JWB Doing with the Downtown Jacksonville Area?

Alex Sifakis serves as the long-term visionary of JWB. Since 2006, Alex has spent a lot of time thinking about the future of Jacksonville, real estate investing opportunities, and ways to improve the local economy. His vision has taken JWB to an exciting point in Jacksonville's history.

With the massive changes caused by the global pandemic, many American workers and corporations are moving to Florida. This migrational shift has made the Jacksonville, FL real estate market super hot for personal non-commercial investment properties. However, there are certain areas of Jacksonville that are underutilized, and that includes Downtown Jacksonville.

Downtown Jacksonville is filled with multiple city blocks with blight issues, deteriorating infrastructure, and run-down office buildings. However, that is changing for the better now that the sale price of properties is going up. 

The founders of JWB have decided to invest their own money into the real estate development of Downtown Jacksonville, so they can create a thriving urban center that attracts young, well-paid, tech-savvy residents. If we can show technology startups, financial services institutions, and major corporations that our city is a gem on the St. Johns River, all of North Florida will benefit.

Why Is JWB so Passionate about Real Estate Investing in Downtown Jacksonville?

Alex Sifakis sees a future in Downtown Jacksonville that will help future market cycles. Alex wanted to buy land, be willing to redevelop downtown Jacksonville, and take action to help out others. JWB and the clients will benefit from what Alex is doing, and the things we have been able to do are exciting.

Downtown Jacksonville needs a walkable, thriving, urban center. Why? Because it will attract companies and young people, raise median incomes, and create excitement. Property values will increase as the area becomes more popular for those who want to invest in real estate. 

Everything we are doing downtown is to grow Jacksonville. JWB wants to make a vibrant downtown, attract more hip, savvy, and well-paid people because it will benefit all of Jacksonville. Population growth and increasing median income will help all JAX properties appreciate quicker. In addition, with more companies coming to the area, a thriving Downtown Jacksonville will emerge as a magnet for people who don't want to live in Atlanta or Miami.

How Can You Tell When the Jacksonville, FL Real Estate Market Is in Growth Mode?

The Jacksonville, FL real estate market has been on a steady growth streak since the 1970s. A mixed-use, walkable downtown is what attracts a hip ecosystem. There is no doubt that this area is in growth mode and will continue to grow as more people move to Florida.

Alex has traveled to other cities via the Jacksonville Chamber Leadership Trip, where city leaders visit other cities to see first-hand what they are doing right. The downtown areas of these cities and schools are where these tours visit, and those city trips helped educate Alex about how downtowns help grow cities. Thus, his vision for Downtown Jacksonville and its redevelopment was born.

JWB operates with a pay-it-forward mentality. Because the JWB team supports Alex's “dream weaving activities,” it allows JWB to develop solutions that no one else is doing. Alex stated that “Doing something good for someone else always comes back to you.” 

What Real Estate Investment Opportunities Are Coming to Downtown Jacksonville?

With the redevelopment of Downtown Jacksonville, more rental property opportunities will soon follow. For example, JWB is trying to correct some infrastructure needs in JAX so more investors will be willing to buy properties in these lower-valued neighborhoods.

To add, JAX is creating a new gas tax to help fund more roads, improve water/sewer, and upgrade the skyway. The JTA is figuring out what that will look like, and mass transit is something JAX is thinking about improving. 

Plus, there is some excitement around a new public greenbelt. The Emerald Trail is a 30-mile trail that goes through neighborhoods and is expected to be a highly desirable recreational trail. The city is funding this Emerald Trail to be developed soon. We see these green belts in Atlanta and Miami, and the properties adjacent to these greenways go up in property value. 

We've toured other cities in Ohio, South Carolina, and Tampa and have seen rental property opportunities explode in these regions. So we're working with Jacksonville's City Hall on picking the best elements of cities so we can apply them here in JAX.

What Will Increase Jacksonville Property Values?

All of JAX is appreciating, and they have since 2012. There is a decrease in blight, and there is an increase in property values. We have been adding to neighborhoods that we are investing in. 

These neighborhoods have improved because of JWB's renovations, and we've seen 20% appreciation year after year in these neighborhoods. Because home prices are going up, we see a continued reduction in blight around the city. 

What Initiatives, in Particular, Are Attracting the Technology Crowd?

We need more amenities and residents. We are attracting a crowd to JAX, and the tech crowd is drawn to vibrant urban centers with lots of great housing, restaurants, and things to do. Any tech company that wants to move to JAX will see a growing number of bars, coffee shops, and other shops that make people want to hang out downtown. 

When we have a thriving downtown, we will attract more tech companies. We've made some serious headway in the big picture development of downtown so far, and we will continue.

What Are the Initiatives That JWB Is Taking Beyond Downtown JAX?

JWB bought the old Town & Country shopping center and redoing it with shops, shipping container homes, landscaping, and infrastructure in Arlington. The goal is to improve the entire neighborhood around this large shopping complex, calling it the College Park Project.

There is a mural that Alex thought of and commissioned. The ROI on a greenbelt trail is $11. The same is true with public art. It increases the property value, even though the art only costs $10K to make, but it adds personality to a neighborhood. 

What's crazy is that at the Douglas Anderson School of the Arts, half of the students gain inspiration from the mural. It's like a park with food trucks and people doing yoga. After restoration, it should be a vibrant public space. 

What we did with the mural was “placemaking.” People stop, look, take a photo, and we decided to add a mural on another property downtown that says #DTJAX for Downtown Jacksonville. Jessica Santiago is the artist who painted the murals, and her work is having a significant impact on #DTJAX.

We are becoming an Instagramable society, and anything we can do to add “Instagramability” to Jacksonville makes it look more likable and desirable. 

If I'm a JWB Real Estate Investor, How Does This Downtown Development Help Me Out?

When it comes to investing in real estate with JWB, we're not just trying to sell someone a house. We're committed to growing every part of JAX, so investors continue to see growth from a vibrant, walkable downtown. More people will want to move here. We expect more people who grew up here will want to stay here if we continue to leverage building houses the right way, manage the properties the right way, and increase investor returns by increasing population growth. 

It's suitable for everyone, and that's why we are so passionate about it. Alex personally wants his kids to live, work, and stay in JAX when they grow up. But, unfortunately, we have too many people leaving for Atlanta, Miami, Greenville, and other areas to go where the jobs are. 

What Is the Key Differentiating Point Between JWB and Everyone Else Offering Turnkey Investment Properties?

The answer is the deep level of Vertical integration. JWB buys the land, builds the homes, renovates properties, manages the properties, redevelops downtown, and plays on a 30-year time horizon. 

We have yet to see other turnkey rental investment property managers doing anything close to the depth of vertical integration JWB is doing in Downtown Jacksonville.

Vertical Integration investment is riskier. That is why JWB is not offering this to investors because the returns are much lower than our single-family property homes. The downtown area has super low rents, dilapidated commercial properties, etc. 

It is too risky to introduce to our community of investors, so we are using our own money to develop this area. However, our Vertical Integration is going to benefit the entire JAX community and our rental property investors.

What Initiatives Does JWB Recommend to Jacksonville's City Hall?

All of the people going on these Chamber Leadership Tours come back to JAX with great ideas to push Jacksonville forward. We want to live, work, and play in JAX.

Alex is known to be a pioneer in trying new things in Jacksonville. Urban centers tend to increase in property value, and JWB has purchased seven blocks — called North Core — to develop into about 1000 residential units, restaurants, shops, and so forth. In about three years, this development will be complete, and it's exciting.

All JWB initiatives are in lockstep with what the Jacksonville DIA wants to do for its master plan. The DIA owns that master plan, and that is why we are in close communication with them, so our visions align. They have 50+ projects in the pipeline, and JWB is only one of the players who will make these projects a reality.

Which Parts of Downtown Jacksonville Is JWB Redeveloping?

Alex showed a map and several slides that are very exciting. For example, the area of Downtown Jacksonville that JWB is investing in is called the North Core neighborhood.

When it comes to investing in real estate in Jacksonville, ​JWB owns the city blocks you see in orange. The other colors represent other real estate development companies.

Our first redevelopment project is in the historic Federal Reserve/218 Church Street/Sweet Pete's complex.

Here is our vision of what the Emerald Trail recreational greenbelt will look like in this artist's rendering.

The Emerald Trail will run adjacent to the courtyard of the Federal Reserve/Sweet Pete's complex we are renovating.

The space inside these historic buildings provides great potential for a hip urban center filled with event spaces, restaurants, coffee shops, and boutiques.

What Technologies in Construction Is JWB Looking at to Reduce the Carbon Footprint?

We are looking at 3-D printing house technology, and we are partnering with a company in Mexico. We are also looking at solar and waiting for a tipping point of affordability and storage of battery power to start investing in that.

How Does Reducing the Carbon Footprint Add Value to the Investor?

If you have solar power, you can raise the rent, and the tenant does not have a power bill. It's a win for the environment, a win for the tenant, and a win for the property owner. We run the numbers on it all the time, and we will let our investors know when we're ready to move forward when the numbers make a ton of sense.

If I Want to Learn More about Real Estate Investing with JWB, Where Should I Go?

If you are thinking about investing in real estate with JWB, tune into our Not Your Average Investor show on Tuesdays and our Property Of The Week on Thursdays to feel more comfortable about our approach. Also, join our Facebook community at

You can also go to to see what properties are currently available. We encourage you to contact the JWB team for a consultation to find out how our property management team can be of service in providing passive income cash flow. 

When you are ready to take the next step with Jacksonville real estate, visit We will walk you through the numbers to show you what your potential Return On Investment will be. 

JWB makes real estate investing as easy as possible. That is why they have been working in the Jacksonville, FL real estate market since 2006 and are busy paying it forward by redeveloping Downtown Jacksonville. That is why the biggest opportunities for real estate investing are uncovered by JWB in Downtown Jacksonville.

To Your Success,

Gregg Cohen

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