On Friday nights, The Loop fills up fast. Cars stream in from Osceola Parkway, families rolling in with windows open. It is a large outdoor complex.
You can smell Chipotle near the Regal Cinemas sign, and kids move quickly along broad, landscaped walkways toward a trampoline park.
The place does not feel random. It was built to feel like a destination. Kissimmee sits right next to one of the most visited tourist corridors in the world.
Back in the early 2000s, Osceola County was growing quickly, and developers were eager to build there. The Wilder Companies, a Boston-based retail developer, saw the opportunity.
In August 2002, the company filed a Florida service mark for "The Loop," covering the leasing and marketing of a regional entertainment, retail, and hotel complex.
The filing made clear the goal: create "buzz" and capture demand from the fast-growing populations in Osceola County and southern Orange County.
Osceola County agreed to reimburse Wilder for land and road improvement costs tied to the project.
As a result, public infrastructure was built alongside the development from the start. The site chosen was at North John Young Parkway and Osceola Parkway.
How The Loop in Kissimmee Was Built, Expanded, and Sold
The main eastern center - 435,000 square feet on nearly 57 acres - was completed in 2005.
Wilder held it for roughly a year before AEW Capital Management bought it for $105 million, making AEW the first institutional owner of the east side.
That sale in 2006 placed The Loop squarely in the mainstream of mid-2000s retail investment, when open-air power centers in growth markets were trading at premium prices.
The western half came later. By May 2008, Loop West was being actively leased and filled, with more than 20 shops, restaurants, and services joining anchors JCPenney, Belk, Circuit City, and Party City.
Both sides were built with wide sidewalks, benches, street lamps, and a landscaped streetscape, a design language Wilder called pedestrian-friendly, even though the center was fundamentally car-oriented.
A county redevelopment document from 2012 noted that the broader Loop area had a theoretical maximum build-out of more than 3.2 million square feet, but that only 730,000 square feet of commercial activity had actually been built by then.
That number matches the current combined square footage of the two centers almost exactly.
Two Centers, Two Buyers, Split Ownership at The Loop
January 22, 2014, brought the first of two major ownership moves that reshaped the property.
An affiliate of North American Development Group, known as NADG, bought Loop West for $52 million from O'Connor Capital Partners.
At that moment, the 295,100-square-foot west center was fully occupied and anchored by Babies "R" Us, Bealls, and T.J. Maxx, with DSW, Party City, and ULTA Beauty rounding out the lineup.
Seven months later, on August 12, 2014, MetLife announced it had acquired the east/main center - 435,000 square feet, 43 tenants, 99 percent leased.
MetLife described it as an outdoor retail center and said it was adding a high-quality retail asset to its portfolio.
From that point forward, The Loop operated as one retail district under two separate owners. NADG kept the west side. MetLife held the east.
Anchors That Came and Went on the East Side
MetLife purchased the east side of the center in 2014, when the tenant mix followed a familiar mid-2000s power center pattern.
CVS, Kohl's, Michaels, Petco, Regal Cinemas, and Sports Authority were key tenants. Toys "R" Us joined the center in 2017.
At that time, a trade report listed a lineup that included Kohl's, Ross Dress for Less, Bed Bath & Beyond, Michaels, Petco, Old Navy, CVS, Famous Footwear, LensCrafters, T-Mobile, Kay Jewelers, Chili's, Chick-fil-A, Noodles & Co., Ben & Jerry's, Chipotle, and Regal Stadium 16.
This was just before a wave of major retail closures.
Sports Authority filed for bankruptcy in 2016. Toys "R" Us closed all U.S. locations in 2018. Bed Bath & Beyond liquidated in 2023.
Noodles & Co. cut back on many of its stores. Major closures left empty spaces that required new tenants.
The east side has since shifted in focus. It now includes more discount retail, specialty food, beauty services, and fast-casual dining than it did originally.
Loop West and the Changing Anchor Lineup
The west side went through its own changes. Circuit City was one of the original anchor stores in 2008, but the company shut down nationwide, and the store closed by 2009.
Bealls later took a place in the anchor lineup and was still there when NADG bought Loop West in 2014. By 2018, it was gone.
That year, a public notice promoted an "Everything must go!" closing sale at the Bealls store in The Loop West Shopping Center.
Babies "R" Us, another anchor listed at the time of the 2014 sale, was also part of the Toys "R" Us liquidation in 2018.
Within a few years, two of the anchor tenants named in the 2014 purchase had disappeared. What replaced them shows a broader change in suburban retail.
The west side now includes JCPenney, Burlington, Nike Clearance Store, Altitude Trampoline Park, T.J. Maxx, DSW Designer Shoe Warehouse, MINISO, Tommy Hilfiger, G by Guess, Talkin' Tacos, BJ's Restaurant & Brewhouse, Bonefish Grill, and other businesses.
Renovations, Leasing, and Foot Traffic on the East Side Now
The east side is being updated. Leasing materials promote a "new look coming soon," along with new inline construction that is available for pre-lease and a preview of planned renovations.
The Regal Cinemas theater is getting several upgrades.
These include a new exterior, recliner seating in all 16 auditoriums except the 4DX screen, and a new premium large-format auditorium alongside the existing Regal RPX auditorium.
Some spaces are still in play. Suite B9 offers 10,750 square feet, Suite B11 - almost 25,000 square feet, and Suite B12 has 35,000 square feet. They are listed as available or under letters of intent.
Foot-traffic data from Placer Labs, covering March 2024 through February 2025, estimates 4.8 million visits per year from about 1 million customers.
The average visit lasts 50 minutes. The busiest days are Saturday, Friday, and Sunday. The busiest hours fall between 5 p.m. and 8 p.m.
The center is open from 10 a.m. to 9:30 p.m. Monday through Saturday, and from 11 a.m. to 6 p.m. on Sunday.
A Grocery Proposal, Loop South, and the Remaining Build-Out at The Loop
A site like this gets a grocer's attention. More than 70,000 vehicles move through Osceola Parkway and John Young Parkway each day, and Loop West has more than 2,000 feet of frontage along Osceola Parkway.
In December 2025, NADG filed plans with the city and the South Florida Water Management District for a 12,500-square-foot grocery store north of JCPenney at Loop West.
The dimensions and layout matched the standard Trader Joe's prototype. Trader Joe's said it was actively looking at neighborhoods in Kissimmee, but it did not confirm the site.
A follow-up in January 2026 said the Loop location was still being discussed as part of the chain's regional expansion.
No lease was signed. No opening date was confirmed.
Another piece was moving at the same time. A leasing brochure for "The Loop South" marketed a planned 50-acre retail development at Osceola Parkway and Thacker Avenue, with 360,000 square feet of space plus outparcels.
It was presented as an extension of the same district.
The bigger development story stretches well beyond that.
Official planning materials set maximum entitlements in the area at roughly 1.53 million square feet of retail and 760,000 square feet of office space, plus hotel rooms and residential units.
Against the current 730,000 square feet built, that leaves a large amount of room still open.
Notable Milestones
2002 - Plans were made for The Loop in Kissimmee as a development focused on shopping, dining, and entertainment.
2005 - The main east side opened as a large open-air retail center.
2006 - The east side entered a new stage following its first major ownership change.
2008 - Loop West expanded the site into a two-part retail area.
2008 - Additional stores and restaurants opened at Loop West as leasing continued.
2014 - Loop West was sold to a new owner.
2014 - The east side was also sold, leaving the two sections under different ownership.
2014 - The east side was almost fully leased with a strong lineup of national tenants.
2017 - Toys "R" Us was added to the east side during a key leasing update.
2018 - Loop West lost Bealls during another round of tenant changes.
2025 - Talkin' Tacos opened at Loop West.
2025 - The property continued to evolve through leasing activity and tenant turnover.
December 2025 - A possible Trader Joe's at Loop West became a topic of public discussion, though it was not confirmed.
2025-2026 - The east side showed continued leasing activity, with open spaces and deals underway.
2025-2026 - Regal at The Loop received upgrades as part of ongoing improvements.
2025-2026 - The Loop stayed active as a shopping, dining, and entertainment destination rather than becoming vacant.
