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With more than 40 years of experience in Florida real estate, mortgage lending, property management and housing-related services, Gidget Jackson helps seniors and their families understand their options and make informed decisions about aging in place, home equity, downsizing, buying or selling a home and transitioning to senior living.
Real Estate • Mortgages • Senior Planning
With more than four decades of experience in real estate, housing, financing, and property-related services, I help seniors and their families understand their options and make informed decisions about the next chapter of their lives.
Whether you want to stay in your current home, explore ways to use your home equity, downsize, purchase another home, find senior services, or simply understand what options are available, my role is to help you put the pieces together.
Senior planning often involves more than one decision. Housing, finances, home maintenance, healthcare resources, transportation, legal planning, and family considerations can all overlap. My goal is to help identify the pieces that may need attention and connect you with trusted professionals and resources when their expertise is needed.
I don't try to be everything to everyone. Instead, I use my experience in real estate and mortgage lending together with a network of senior-related professionals to help you find the right resources and ask the right questions.
My experience spans real estate, mortgage lending, property management, insurance, investment properties, new construction, distressed properties, and senior-focused planning. Over the years, I have continued my education through specialized professional designations and certifications so I can better serve clients with complex housing and planning needs.
Florida Licensed Real Estate Broker — licensed since 1985; Broker since 1987
Licensed Mortgage Loan Originator — NMLS #1874329
Notary Public — Remote Online Notary (RON) Certified
SRES® — Seniors Real Estate Specialist
STS — Seniors Transition Specialist
CREV — Certified Reverse Mortgage Specialist (NAMB)
ABR® — Accredited Buyer's Representative
CFS — Certified Foreclosure Specialist
SFR® — Short Sales & Foreclosure Resource
RSPS — Resort & Second-Home Property Specialist
CDPE — Certified Distressed Property Expert
AHWD® — At Home With Diversity
GREEN — NAR's Green Designation
e-PRO®
CLHMS — Certified Luxury Home Marketing Specialist
Certified Senior Advisor (CSA) — In Process
After decades of working with homeowners, buyers, sellers, borrowers, families, and investors, I saw how complicated decisions can become as we get older. Often, the question isn't simply whether to sell a home or obtain a loan—it's how that decision affects everything else.
I created Senior Planning Advisor to provide a place where seniors and their families can explore their options, find helpful resources, and have someone help them connect the pieces. My goal is not to tell you what you should do, but to help you understand your choices so you can make the decision that is right for you.
Every situation is different, so we start with what matters most to you. Together, we can explore options for staying in your home, downsizing or relocating, buying or selling a home, using home equity, financing, finding senior services, and preparing for future needs.
When your situation requires expertise outside my professional role, I can also help connect you with trusted senior-related professionals and service providers.
I believe good planning starts with listening. There is rarely one solution that is right for everyone, especially when decisions involve your home, finances, independence, and family. My approach is to listen first, explain the available options in understandable terms, and help you identify the questions that need to be answered before making a decision.
Sometimes the best decision is to stay exactly where you are. Sometimes it's time to make a change. Either way, the goal is to help you move forward with greater clarity and confidence.
Born in Hialeah, Florida, and raised in Miami and Central Florida, I have always loved the Florida lifestyle. I began my professional career in Central Florida in 1985, initially working in insurance and real estate. After earning my real estate sales license, I became active in the local Board of Realtors and obtained my Florida real estate broker's license in 1987. I went on to own and operate Jackson & Associates Insurance and Investments before relocating to Southwest Florida in 1990.
After moving to Southwest Florida, I joined Century 21, became a top-producing real estate professional, and helped train new agents. I also expanded my knowledge of mortgage financing—an area that would later become an important part of my professional career.
In 1991, I purchased a property management and maintenance company responsible for 397 properties and a full staff of employees. My work included property management, maintenance coordination, real estate sales, apartment-to-condominium conversions, and management of condominium associations during developer turnover. The portfolio ranged from single-family homes and small multifamily properties to apartment complexes and commercial properties.
I also worked with property owners, investors, and lenders on the financing and refinancing of investment portfolios, preparing property information and coordinating transactions. This experience gave me a strong understanding of how real estate, financing, property condition, income, and long-term planning often intersect.
As the market changed, my work expanded into new construction, where I sold new homes and managed rental properties for a local builder. Later, I was hired to manage and market condominiums in two large Fort Myers developments that had gone through foreclosure. Over several years, I helped coordinate the renovation, management, marketing, and sale of approximately 210 units as the properties transitioned from investor ownership to individual owners.
From 2000 to 2010, I owned and operated two RE/MAX franchises in Cape Coral and Fort Myers with more than 50 associates and employees. Our offices handled residential and commercial real estate as well as property management, earning numerous multimillion-dollar sales awards. Following the recession, I relocated to the Florida Keys, where my work expanded to include affordable housing and the unique real estate challenges of the Keys. I later returned to RE/MAX as a Broker Associate in 2018.
In 2019, I expanded my professional services into mortgage lending, allowing me to better understand and assist with the financing side of a real estate decision. Since then, I have worked with a variety of mortgage programs and developed a particular interest in helping older homeowners understand home equity, reverse mortgages, and financing options that may support their retirement and housing goals.
Today, I continue to work directly with clients as both a real estate professional and mortgage loan originator, giving me the ability to look at housing decisions from more than one perspective. My experience includes residential real estate as well as Conventional, FHA, VA, USDA, reverse mortgage, and investment financing. This combination of experience is especially valuable when helping seniors evaluate whether to remain in their current home, access home equity, downsize, purchase another home, or consider other housing options.
Throughout my career, I have worked through many different real estate markets and helped clients navigate both opportunities and challenges. Much of my business has come from referrals from past clients, friends, and families—relationships I value greatly. Today, I bring that experience together through Senior Planning Advisor, helping seniors and their families explore housing, financing, home equity, real estate, and senior-resource options with education and personalized guidance.
You don't have to have everything figured out before reaching out. Sometimes the best place to start is simply with a conversation about where you are today, what concerns you, and what you would like the next chapter to look like.
Whether you're planning ahead, facing a decision now, or helping a family member explore their options, I'm happy to help you identify possible next steps and resources.
