Buying a House in Orlando Near Walt Disney World: The Inside Story

Orlando Real Estate Advice

Expert Advice on Orlando Real Estate from Local Realtor Thevi Jackson

Where to begin if you’re thinking of buying a home in the Orlando area from someone who really knows the real estate market in and around Walt Disney World

For any longtime fan of Walt Disney World Resort, the prospect of buying a home close to the magic is something that likely crosses your mind from time to time. I know that it does for me. With that in mind, I thought I would get some advice and input on the Orlando real estate market from a local expert. And not just any local expert, but an Orlando-based Realtor who specializes in properties in and around the Walt Disney World Resort area.

So if you are thinking of taking the Florida plunge in Orlando, I hope that you find this post useful.

Thevi Jackson, Orlando Realtor and Disney area specialist.

Thevi Jackson is an Orlando Realtor and Disney area specialist.


I had an opportunity to spend some time with Ms. Jackson to get her thoughts and insights on Orlando real estate and how to approach the market for those considering purchasing a property in the area. Here are some highlights from our Q&A.

Q&A with Orlando Realtor, Thevi Jackson

MB: As a Luxury Disney Travel Blogger, I focus on everything to do with upscale Disney vacations — primarily to Walt Disney World, but also including other Disney destinations. But since Walt Disney World is a such a large place and because Orlando has a tourism-driven economy, it’s the Disney destination where I spend most of my time.

Since you are an experienced Orlando Realtor who specializes in properties in and around Walt Disney World Resort, can you tell me a bit about yourself and how you ended up focusing your business on Disney-related properties?

TJ: Certainly!  I am a second generation REALTOR®, with Follow Me Realty, originally hailing from Fort Lauderdale, Florida. Like you, I grew up going to Walt Disney World with my family and developed a lifelong love for Disney Cinema and the Disney Parks.  When I had a family of my own I passed my love of Disney on to them, vacationing on or offsite at least once per year. 

I remember vividly every time it came time to go home I felt such a terrible malaise, and it always seemed like I was counting down the days until my next Disney vacation.  One day I woke up and said, that’s it, it is time to follow my happiness.  My husband took some convincing, but ultimately we decided to take the plunge and move to Orlando, and we have never looked back.  One thing I remember about my move here was feeling so overwhelmed and having real difficulty finding information on great neighborhoods and school districts with proximity to Disney. 

Since settling in Windermere, I have made it my mission to become the Realtor who is the true authority on the wonderful neighborhoods and homes that surround the Disney parks (I even know where to find the best fireworks views).

Orlando home

Courtesy of Thevi Jackson on Instagram @YourHomeAgent.


We’ve often thought about purchasing a property somewhere nearby Walt Disney World, but really don’t have any insights into the local real estate market. So let’s start with your high level thoughts on the Orlando real estate market.

How would you describe the market there, generally speaking, for someone who doesn’t currently live in the area? Can you share your thoughts on local schools, family-friendly areas, the types of homes one can expect to find there, and so on?    

I would start by saying that Orlando is an excellent market to invest in, whether you are buying a primary residence, a vacation home, or an income-generating property. Orlando is experiencing steady growth — home prices rose 10% over the past year and they will continue to rise, making Orlando a strong and solid market. 

The Disney area offers gorgeous neighborhoods with a fit for every architectural preference, whether you prefer a most historic feel that can be found in downtown Windermere or Winter Garden, or a brand new custom home in Horizon West or Disney’s Golden Oak Estate. 

Beyond the parks you will find incredible arts, culture, dining, and shopping all throughout Orlando. As far as education is concerned there are a plethora of top notch options throughout the city. Whether you are looking for private, magnet, charter, or public schooling, there are exceptional options for every child. I like to refer to my clients to www.greatschools.org when researching education options; it is a wealth of information, far more than I could provide.

If someone new to the greater Orlando area was interested in purchasing an upscale home within an easy drive of Walt Disney World, what areas or neighbourhoods should they consider? What should they be thinking about and were would they start their search?

I would first advise them to call me.  As a Disney area expert who focuses on luxury properties and clientele I have intimate knowledge of the high-end inventory throughout the Disney sphere. I can tailor a tour of homes that specifically meets each of my clients’ needs and desires in a home and neighborhood, whether that be architectural style, view, proximity to park, amenities, gated/security etc.

Disney door knob.

Courtesy of Thevi Jackson on Instagram @YourHomeAgent.


Are there any particular things to think about if someone is interested in more of a vacation home (so only for part of the year) versus a permanent home that they plan to live in year round?

Absolutely, these are great items to speak about in our initial consultation. 

Without going into too lengthy detail; you would want to consider asking yourself whether you would be sharing this home with relatives throughout the year, would you want to make it a short-term rental property for some added income, what sort of amenities would you like to have available to you on your vacation, do you prefer to have your vacation home in a typical neighborhood setting rather than a resort style setting? Home owner association rules and regulations differ greatly as do amenities and we would want to make sure to find the right neighborhood and home to suit your desires. 

There are quite a few luxury communities close to Disney that are exclusively vacation homes or short-term rentals. Regardless of what strikes you fancy I will always work hard to find the best options for you.

What about buyers from outside the country — such as Canadians like me? Do you have any experience or insights into special needs or circumstances that may affect foreign buyers?

First I would say Welcome, or maybe to you being from Canada, Bienvenue!  And tell you how excited I would be to work with you. However, I will refrain from advising you — or any foreign buyer — on this topic because being a REALTOR® and local expert does not qualify me to give legal assistance or advice. 

What I can do is be your concierge to make this process smooth and unencumbered.  I have quite a few trusted real estate professionals in my wheelhouse, such as lawyers, FIRPTA experts, lenders etc., who can provide specialized guidance through the process of purchasing real estate as a foreign national.

DIsney's Golden Oak homes in Walt Disney World

DIsney’s Golden Oak homes in Walt Disney World.


I’m really curious about the Golden Oak Estate homes on Disney property. Do you have any insights or thoughts on whether these are a good option as opposed to other homes close to Disney property? Is there value for your dollar there — I’m assuming there is a premium price on those properties because they’re on Disney property? Are there any limitations or special situations to be aware of because they are on Disney property?

To quote Golden Oak’s Website: “Welcome to a world embraced by luxury, privacy, and the Magic of Disney. This magnificent resort community offers first-ever whole ownership of custom single-family homes at Walt Disney World® Resort.”

The Golden Oak Estate offers a Disney Lifestyle that truly embodies luxury, imbues magic and exceeds expectations. Homeowners may choose from a variety of architectural styles, floor plans and unique upgrades for their homes. Each home offers exclusive views of Walt Disney World fireworks and your choice of nature, water or golf course vistas.

With resale homes starting at two million dollars and above, Golden Oak must epitomize Walt Disney World’s legendary magic. And I can tell you from personal accounts, it does not disappoint. This Disney lifestyle community offers everything in one place that a luxury Disney connoisseur such as yourself has come to appreciate. From the Clubhouse, Tranquilo Golf Course, Concierge at the onsite Four Seasons Resort, exclusive events, and nightly fireworks views — your world is immersed in Disney magic.

As long as there are lovers of all things Disney and Walt Disney World, I believe there will be enduring value in Golden Oak. It may not be the right fit for every Disney lover’s tastes and budget, but to many discerning clients interested in the best of Disney living, there is no other choice.

Golden Oak — like many communities in Orlando — has neighborhood rules and regulations that must be abided by. However, barring budget, I know of no restrictions of which to be wary.

What else should a potential buyer need to know? Is there anything important that I have missed or that you would like to add?

Great question Mike! The National Association of REALTORS® has some tips for buying in a tight market and Orlando definitely qualifies as a tight market:

  1. Determine and stick to a budget.
  2. Identify desired neighborhoods and home wants, versus needs.
  3. Be ready to make a decision quickly.
  4. Bid competitively and limit contingencies.
  5. Work with a Realtor®

…and I would love to be that Realtor!

Thevi Jackson family at Disney's Animal Kingdom Park.

Thevi Jackson (center) and family enjoying Disney’s Animal Kingdom Park.


If someone were interested in learning more about buying a home in the Walt Disney World or Orlando area and they wanted to consult with you, what is the best way for them to contact you?

The fastest way to contact me is by phone (407) 488-2426. I am also available via email: [email protected]  and on Facebook @yourhomeagentorlando.

Thank you very much for taking the time to speak with me about Orlando real estate near Walt Disney World. it has been very educational!

My pleasure Mike. Thank you as well.

Looking for more great stories and information about Walt Disney World?

Be sure to read my Guide to Planning A Walt Disney World Vacation and my post on the Five Golden Rules of Walt Disney World Vacation Planning.

Also, be sure to subscribe to the free Luxury Disney Travel Newsletter for the latest features on Disney travel and curated news prepared just for you.

Mike Belobradic: The Finer Side of Disney Travel
Luxury Travel Blogger – Deluxe Disney Travel Specialist
The Finer Side of Travel™ #LuxuryDisney