About Shena
Led by Shena Omotola, M.B.A. — Broker-Owner of Skyward Realty & Dream Home Specialist™
At Skyward Realty, we’re more than just brokers — we’re a dedicated team of Dream Home Specialists™ committed to helping you buy or sell with confidence. Whether you’re moving across the street or across the country, we proudly serve clients throughout Chicagoland, Northwest Indiana, and Central & Coastal Florida with integrity, strategy, and care.
Our mission is simple: to understand your goals, your lifestyle, and your long-term vision so we can guide you toward the perfect home. From first-time buyers to luxury clients and out-of-state relocations, we deliver concierge-level service backed by experience and heart.
How We Help You: Buying your first home, Selling for top dollar, Luxury property marketing, Relocating to another state, Military relocation and VA loan support, Upgrading, downsizing, or investing.
Meet Shena Omotola, M.B.A.
Broker-Owner of Skyward Realty | Certified Luxury & Relocation Specialist | Dream Home Specialist™
Licensed in IL, IN & FL
A lifelong Chicagoland native now based in Northwest Indiana, Shena Omotola is the visionary behind Skyward Realty. With nearly 20 years of residential real estate experience, Shena is known for her sharp negotiation skills, warm professionalism, and unwavering dedication to her clients’ success.
She holds certifications including:
LHC® – Luxury Homes Certification
RSPS® – Resort & Second Home Property Specialist
RENE® – Real Estate Negotiation Expert
MRP® – Military Relocation Professional
Shena launched Skyward Realty in 2016 to create a brand that rises above the traditional — one built on transparency, elevated service, and expert representation. Her background in corporate media and marketing gives her a unique edge when positioning homes in a competitive market, while her passion for helping others shines in every client interaction.
Whether you're purchasing your first home, relocating to a new state, or moving up into your dream lifestyle property, Shena and the Skyward team are ready to help you rise — Skyward.
Prestige. Expertise. Possibility.
Turning Your Real Estate Goals Into Reality.
Transaction History
- 1 Year
- 2 Year
- 5 Year
Neighborhoods Shena Has the Most Experience In
Shena's Listings and Deals
Shena's Active Listings
Awards and Designations
- ALHS - Accredited Luxury Home Specialist
- CNE - Certified Negotiation Expert
- MRP - Military Relocation Professional
- RSPS - Resort & Second-Home Property Specialist
Other Experience
Shena's Reviews
5/4/21Charlie Barnes
Shena is a professional and very knowledgeable with Real Estate. She was able to perform dead-on comps, give input to help prepare the homes for the current market. Very detailed and very much in the loop. I never felt that I was second in her list.
Great communication and very attentive to the process which helps with the overall stress of the process. She is a real pusher! She Listed my house on Saturday, and I had a contract on Sunday (yes! One day). With the Real Estate market / current environment, you need someone that known the system and can get it done!
We were able to sell a couple properties and find our dream home in this crazy market. She NEVER slipped or wavered. Thank you Shena for the “A” game.
5/3/21Terriun Crump
I would not be honest if I called Shena a realtor. She is much more than that. She has been a realtor, advisor, therapist lol through this home selling & buying process. She has help make this transition as less stressful as possible. She is family.
10/15/20Dr. Mariah Payne
Shena was the absolute best realtor I have ever worked with. She is very profesional and knowledgeable in the field. During my time and process of purchasing my first home she was on top of everything for me and made sure she did what she had to to fight and get me the house of my dreams! I am forever grateful for all of Shena’s hard work and dedication she gave to me during this process. She is the best when you ever need a realtor whether it’s Chicago or Indiana she is your go to!!!
