Live, Grow & Invest in Southwest Florida

Your Dream Life Is Waiting for You

Which Community is Right for You?

There has never been a better time to live your best life right here in Southwest Florida. Whether you are looking for a family-centred community, the boats & beaches lifestyle, a premier gated community, or the best golfing, The Village Guru has curated all the best options for you to see.

Southwest Florida has everything and anything you could possibly want, you just have to know where to look. When you work with The Village Guru, you will receive all the knowledge, strategy and expertise to find your new dream home and life. Let's get started!

We are Your Gulf Coast Experts!

For those of you moving to Florida, but don't know the details of each Gulf Coast city, you may not know exactly where you are going to buy yet...and thats ok!

The Village Guru Team includes agents located from St. Pete to Naples, and we will ensure you've seen all of your options before making such a big decision.

The Village Guru Team uses proven processes to ensure we find you not only the perfect home, but your dream lifestyle as well. We are your one-stop-shop for all your real estate needs!

Let us Show You the Gulf Coast

St. Pete & Clearwater

The Keys


Lakewood Ranch



Fort Myers


You Deserve More than a “sales Agent”

Buy & Sell with The Village Guru

The Village Guru was founded by Jeffrey O’Leary, who has over 15 years of experience managing client projects to list and purchase homes. Over the last 10 years, he has consistently been in the top 1% of his market and Jeffrey’s brand, The Village Guru, has been changing the way real estate is done. We say that anyone can sell a house, but we believe that 360° client satisfaction requires complete project management, with better technology, procedures, communication, and strategy. We treat your home sale or purchase like the major life changing event that it is, and you are hiring a Project Manager, Expert Strategist, Competent Advisor, Modern Marketer, and Savvy Negotiator. 

Proven Systems & Procedures

We don't wing it or fly by the seat of our pants here. Every successful listing and purchase has specific tasks, benchmarks and conditions that must be met. Our proprietary Seller & Buyer Systems ensure problems are identified and avoided long before they are ever an issue. We make sure the whole job gets done to the highest standard.

Client Education & Communication

We will never pressure you into a sale, because that never creates trust or respect. We are your guides and educators so that you are empowered to make the best decision for yourself. We will show you all the related market data AND put it into context (this is critical) so that you are confident in your price and your strategy from day 1.

Modern Marketing Strategies

When you sell your home with The Village Guru, you're not hiring one person, you're hiring a team of professionals, all dedicated to their craft to ensure your listing is presented at its best and get wide exposure, especially online. We will advertise locally on facebook, all the way to internationally, depending on the needs of the listing. Effective marketing will draw ideal buyers to your home like a magnet.

Expert Management Skills

When you choose a real estate company, you are really choosing who will make the process the most successful. It's not just the final act of a purchase or sale, but how much stress did you incur? How easily did the process flow? How confident were you knowing what was going on? How much were you communicated with at key moments? How much did your agent guide you through an efficient process?

The real skills that will not only sell or buy your home, but ensure a better experience for you, are the ability to:
- Communicate effectively with you
- Manage your sale/purchase like a project
- Lead and manage all parties involved
- Problem solve situations calmly
- Negotiate your purchase or sale like a boss

The Village Guru is committed to providing each an every client the white glove service they deserve, because we want clients for life!

Jeff OLeary The Village Guru

Book A Discovery Call with Jeff

Book a zoom meeting so that we can have a no-pressure, no obligation conversation about your needs.
You will speak with Jeff personally, not a sales agent, because learning about you is the most important step to creating your personalized sales strategy. The first step in a great relationship is building trust through honest communication.