Upwell Realty

Upwell Realty A boutique real estate brokerage offering award-winning service throughout the Orlando Metro Area. Kyle has been an Orlando real estate agent since 2013.

In addition to being Gold Key Certified for Excellence in Professionalism by the Orlando Regional Realtor® Association, he has consistently performed in the top 1% of real estate agents in the Orlando area and has been recognized as a Top 100 Agent by Orlando Real Producers Magazine. Fortified by numerous agent of the year awards and a HomeLight top producer designation, Kyle is a former chairman

of his previous brokerage’s Agent Leadership Council. A Certified Luxury Home Marketing Specialist (CLHMS) and Million Dollar Guild appointee, Kyle has achieved top performance levels in the luxury sector. Still, he provides the same high-touch service to all clients, regardless of price point. After growing up in Chicago’s west suburbs, Kyle studied public relations at Bradley University, where he obtained an advanced internship in guest relations with The Walt Disney Company. Kyle quickly fell in love with Orlando while making his mark at Walt Disney World, earning positions as a Magic Kingdom tour guide and as a VIP guide for celebrities and visiting dignitaries. Through Disney’s extensive training regimen and Kyle’s hands-on experiences in these unique roles, he developed the high standards of personalized service and attention to detail for which he is known. Recruited to Greenwich, Connecticut, as the executive administrator for the former CEO of Lord & Taylor and chairman of the board of Ann Taylor, he further engaged his talent for delivering singular client experiences. After Hurricane Katrina hit New Orleans, Kyle and his wife, Shalea, relocated to Louisiana to help her parents rebuild their company. Shalea and Kyle used their acumen to assist with the expansion of her family’s wedding business into the No. 1 venue in New Orleans and a destination for weddings throughout the region. After seven successful years of growth, and spurred by his own experiences in the field, Kyle sought a new challenge with a new ceiling: real estate. Real estate professionals, according to Kyle, are not salespeople but service providers. Motivated by a genuine commitment to his clients’ goals and happiness, he channels his broad experience to exceed expectations throughout every transaction. Kyle’s business mindset centers on collaboration: Every client — from first-time homebuyers to luxury property investors and relocators — receives Kyle’s equal care and attention as they find real estate success together. Aided by Kyle’s advanced problem-solving skills and tech-forward approach, success is the only outcome. Kyle met Shalea while working at Disney World, and the couple now enjoys sharing their love of the Disney theme parks with their two sons. A Life Loyal member of the Sigma Chi International Fraternity, he finds time to give back to his community through volunteering and through automobile clubs in Central Florida.

Check out this property just listed in 32832
06/02/2026

Check out this property just listed in 32832

Check out this listing! 5 beds | 4 baths | 4,010 sq. ft. - Priced at $2,949,000 Experience refined lakefront living on beautiful Lake Whippoorwill in the highly sought-after Lake Nona area, just minutes from Medical City. Contact me for details! 10633 LAGO BELLA DRIVE | ORLANDO | FL 32832 @ CASTLE R...

Today we’re celebrating Kyle! 🎉 Thank you for your vision, dedication, and everything you do for the team each and every...
05/31/2026

Today we’re celebrating Kyle! 🎉 Thank you for your vision, dedication, and everything you do for the team each and every day.

We’re grateful for the positive impact you’ve made and all that you continue to build. Wishing you a year filled with continued success, happiness, and plenty of reasons to celebrate!

Check out this property just listed in 34786
05/30/2026

Check out this property just listed in 34786

Check out this listing! 5 beds | 6 baths | 6,182 sq. ft. - Priced at $3,750,000 Under Construction. Contact me for details! 9960 6TH STREET | WINDERMERE | FL 34786 @ NOVA REAL ESTATE SERVICES INC

Check out this property just listed in 34786
05/30/2026

Check out this property just listed in 34786

Check out this listing! 4 beds | 3 baths | 2,816 sq. ft. - Priced at $1,250,000 Calling all car enthusiasts or artisans needing a large, detached workshop on your property! Contact me for details! 5128 BUTLER RIDGE DRIVE | WINDERMERE | FL 34786 @ LOKATION

🛌 3 🛀 2 🚘 2📍 1035 Chase Drive, Winter Garden, FL, 34787Our latest sale on RateMyAgent.Real Estate Sales SL3278229https:/...
05/29/2026

🛌 3 🛀 2 🚘 2
📍 1035 Chase Drive, Winter Garden, FL, 34787

Our latest sale on RateMyAgent.
Real Estate Sales SL3278229
https://rma.reviews/n44dnw8eg7vy
..

Check out this property just listed in 34786
05/28/2026

Check out this property just listed in 34786

Check out this listing! 5 beds | 5 baths | 3,695 sq. ft. - Priced at $1,299,000 One or more photo(s) has been virtually staged. Contact me for details! 2002 WATER KEY DRIVE | WINDERMERE | FL 34786 @ COMPASS FLORIDA LLC

Check out this list before putting in an offer. What else is a deal breaker for you?
05/28/2026

Check out this list before putting in an offer. What else is a deal breaker for you?

How many times have you heard the story about people who move into their dream home only to find out...

Check out this property just listed in 34786
05/23/2026

Check out this property just listed in 34786

Check out this listing! 5 beds | 4 baths | 3,064 sq. ft. - Priced at $1,349,000 Spacious and beautifully maintained 5-bedroom, 4-bath pool home situated on a 1/2-acre fenced treed lot in desirable Estates at Windermere. Contact me for details! 2230 RIDGEWIND WAY | WINDERMERE | FL 34786 @ COLDWELL BA...

Address

603 E Colonial Drive
Orlando, FL
32803

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