Jeremy O’Guinn, Naples Real Estate Advisor
Jeremy O’Guinn is a Naples, Florida Broker Associate and Certified Negotiation Expert (CNE) with Downing-Frye Realty and more than 18 years of Southwest Florida real estate experience. He represents buyers and sellers of luxury, waterfront, and golf community homes in Naples, Bonita Springs, Marco Island, and Estero.
Real estate decisions in Naples often involve high stakes, limited time windows, and real financial risk. Jeremy’s role is to bring clarity to that process, with accurate information, steady representation, and a clear strategy, so clients move forward informed and confident rather than rushed.
A Florida Native With Deep Naples Roots
Background and local experience in Naples and Southwest Florida
Jeremy grew up in Ocala, Florida, and earned a Bachelor of Science in Psychology from Florida State University. Before real estate, he served as an Assistant Branch Manager at Regions Bank, where he learned to guide people through important financial decisions with patience and precision.
He moved to Naples and earned his Florida real estate license in 2008, then his broker’s license in 2010. Living and working here for more than 18 years has given him firsthand insight into local neighborhoods, pricing trends, seasonal demand, and waterfront dynamics across communities from Port Royal and Pelican Bay to Bonita Springs and Marco Island.
A Career in Naples Real Estate
Jeremy O’Guinn’s education and career timeline
- 2005Florida State University
B.S. in Psychology, the foundation for how he listens, advises, and negotiates.
- BankingRegions Bank
Assistant Branch Manager, guiding clients through financial decisions.
- 2008VIP Realty
Earned his Florida real estate license and began practicing in Naples.
- 2010 to 2011Broker & Royal Shell
Earned his Florida broker’s license in 2010 and joined Royal Shell Real Estate in 2011.
- 2014 to TodayDowning-Frye Realty
Broker Associate and Certified Negotiation Expert serving Naples and Southwest Florida.
A Calm, Data-First Approach to Naples Real Estate
Pricing, negotiation, and discretion for Naples buyers and sellers
Precision Pricing
Every recommendation is grounded in current Naples sales and firsthand market experience. Pricing guidance reflects what the market actually supports, not an inflated number designed to win a listing.
Strategic Negotiation
Calm, methodical advocacy built on the Certified Negotiation Expert framework, protecting your price, terms, and net proceeds at every stage of the transaction.
Discretion
Direct, consistent communication and privacy-forward representation when confidentiality matters, for high-value sellers and buyers who prefer to limit public exposure.
Negotiation Experience and Professional Credentials
Certified Negotiation Expert and Florida real estate broker
Jeremy holds the Certified Negotiation Expert (CNE) designation, reflecting advanced training in negotiation strategy, offer structuring, and contract analysis. Paired with his background in psychology, it shapes a style that emphasizes preparation, listening, and steady execution rather than reactive decisions under pressure.
He has facilitated more than 200 transactions in the Naples area, representing buyers and sellers of single-family homes, condominiums, waterfront properties, and luxury estates.
For Sellers
A disciplined pricing and negotiation framework designed to protect net proceeds, with marketing built around how luxury buyers actually search.
For Buyers
Objective community insight, offer positioning, and contract terms structured to reduce risk and protect long-term value.
Representing Buyers and Sellers Throughout Southwest Florida
Naples, Bonita Springs, Marco Island, Estero, and Fort Myers Beach
Jeremy represents clients across a range of property types and price points, from primary residences and seasonal second homes to waterfront estates and investment properties, with particular depth in luxury and waterfront communities throughout Collier and Lee Counties.
Much of his business comes through referrals and repeat clients, a reflection of outcomes-focused representation rather than volume-driven practice.
Living the Naples Lifestyle
Golf, boating, family, and exploring new places
When he is not working with clients, Jeremy enjoys golf, time on the water, and spending time with his family, along with exploring new places whenever the calendar allows.
Living the same lifestyle his clients are moving here for keeps his perspective grounded and his local knowledge current, from the best boating access to how a golf community actually feels on a Tuesday in July.
What Clients Say About Working With Jeremy
Naples real estate reviews from buyers and sellers
“Jeremy was very prepared and he listened to what we wanted and made adjustments based on our preferences. He didn’t try to talk us into something that was too expensive or wrong for our needs.”
“He listens to what you are looking for and shows you the appropriate properties. He does not waste your time and is very responsive. Jeremy will be our realtor for life.”
“No question one of the best realtors I have ever worked with. Jeremy was never pushy and very understanding of our needs and came with all solutions to anything we needed.”
“Very patient and impartial. Did not seem to have his own agenda. Responsive and flexible. Will be recommending to friends and colleagues.”
“Jeremy is extremely knowledgeable and helpful about the properties he represents. He made the process of buying a home so easy that I would strongly recommend him to all of my friends and family.”
“Jeremy, thanks for helping us make our dream come true! Jeremy is very easy going, understanding and would keep in touch and follow up appropriately.”
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About Jeremy: Common Questions
Experience, credentials, and service areas
Who is Jeremy O'Guinn?
Jeremy O’Guinn is a Naples, Florida Broker Associate and Certified Negotiation Expert with Downing-Frye Realty. He has more than 18 years of Southwest Florida real estate experience and has facilitated more than 200 transactions in the Naples area.
What is a Certified Negotiation Expert (CNE)?
The CNE is a professional real estate designation that reflects advanced training in negotiation strategy, offer structuring, and contract analysis. Jeremy uses it to protect his clients’ price, terms, and net proceeds.
How long has Jeremy been in real estate?
Jeremy earned his Florida real estate license in 2008 and his broker’s license in 2010. He has been with Downing-Frye Realty since 2014.
What areas does Jeremy serve?
Jeremy serves Naples, Bonita Springs, Marco Island, Estero, Fort Myers Beach, Sanibel, and Captiva, with particular depth in luxury, waterfront, and golf communities in Collier and Lee Counties.
Does Jeremy represent both buyers and sellers?
Yes. Jeremy represents buyers and sellers of primary residences, seasonal homes, condominiums, waterfront properties, and luxury estates throughout Southwest Florida.
How do I contact Jeremy?
Call or text 239-963-4474, email jeremy@naplesnest.com, or visit the contact page to schedule a 15-minute consultation. During business hours, he responds within the hour.
Start a Thoughtful Conversation
Whether you are considering buying or selling in Naples, evaluating your options, or simply planning ahead, Jeremy welcomes the chance to answer your questions without pressure or obligation.