North Orlando Avenue / US 17 and 92 and West Canton Avenue
Winter Park, Florida

Greater Orlando's first fully-enclosed mall was built on a 40 acre plot, located 3.4 miles northeast of the center city, in suburban Winter Park. Enveloping approximately 459,000 leasable square feet, the complex was designed by Atlanta's Toombs, Amisano & Wells firm and developed by Jacksonville's Morris Alpert.

WINTER PARK MALL was officially dedicated August 20, 1964 and was the Sunshine State's fourth air-conditioned shopping center. The 10 million dollar complex was co-anchored by a 2-level (120,000 square foot), Charlotte-based J.B. Ivey. The thirteenth store in the chain, it had opened for business August 6, 1964.

Ivey's was joined by a 2-level (120,000 square foot) J.C. Penney, and forty-four inline stores, on August 20. The WINTER PARK "Penneys" was one of the first full-line, "New Look" stores.

Charter tenants included Walgreen Drug, Schwobilt Clothes, Bill Baer's Music, Lillie Rubin ladies' wear, Lawton's Jewelers, Singer Sewing Center, The Mall News, Toy & Hobby Chest, Anita Mengle Studio and an F.W. Woolworth 5 & 10.

In the early years, contemporaries of WINTER PARK MALL were COLONIAL PLAZA (1956 & 1962) {3.3 miles southeast, in Orlando}, ORLANDO FASHION SQUARE (1973) {3.2 miles southeast, also in Orlando} and ALTAMONTE MALL (1974) {4.2 miles northwest, in Altamonte Springs}.

A fire broke out in WINTER PARK MALL on April 6, 1969. There was severe damage to Lawton's Jewelers, Keller Music Company, Allied Radio Shack, Schwobilt Clothes and Wig Land. Repairs were made and all affected tenants were back in business by August 1 of the same year.

By this time, the Park Avenue district {1.5 miles southeast, in Winter Park} had become a major rival. This center city area had begun a move toward the upscale, with the completion of its Greeneda Court shopping complex, in 1945. By the early 1960s, Park Avenue was promoted as "Florida's most unique shopping district."

As a competitive measure, the WINTER PARK property was given a 2 million dollar renovation in the mid-1980s. The project, carried out by Southern California's Macerich Company, installed new flooring, skylights and landscaping. Two 60-foot glass towers were added to the mall's Main Entrance.

New stores also joined the retail roster. These included Piece of Pie, Corn Dog 7 and Regis Hairstylists. Work commenced in mid 1985, with a formal re-dedication held on November 1st. WINTER PARK MALL now contained seventy-three stores and services.

The only anchor rebranding in the mall's history converted Ivey's into a Dillard's. This took place June 4, 1990. The April 1993 defection of J.C. Penney, to a new store at FASHION SQUARE MALL, can now be seen as the beginning of the end for WINTER PARK MALL.

By mid-1994, the owner of the shopping hub, Orlando Regional Center Associates, had nearly given up on a plan to reposition and retant the dying complex as an enclosed upscale fashion mall. In 1996, a joint venture was formed with Columbus, Ohio's Don M. Casto Organization.

Plans for WINTER PARK TOWN CENTER were made public in August. The mall, which now had just one operational store (Dillard's), would be rebuilt as an open-air lifestyle center. Dillard's was to be retained and expanded with a third level. A freestanding Chamberlin's Market & Cafe would also be left standing.

WINTER PARK MALL was demolished between May and October 1998. In March 1999, Borders Books and P.F. Chang's China Bistro became the first tenants to open in the new complex, whose name had been changed to WINTER PARK VILLAGE.

Dillard's upset the apple cart, so to say, when they closed their store, on August 16, 1999. The budding retail and office center was, all of a sudden, without a department store anchor. The problem was solved when it was decided to section the lower level of the vacant Ivey's / Dillard's into seven inline store spaces. The upper level was refitted with fifty-eight loft apartments.

An official dedication was held for WINTER PARK VILLAGE November 15, 1999. The complex included 350,000 square feet of retail and 114,000 square feet of office space. Stores and services in the complex included Micro Centers, Albertsons, Harper's Tavern & Bistro and Athletic Attic.

The Regal Winter Park Village 20 megaplex showed its first features December 3, 1999. Early in the 21st century, Cheesecake Factory, Ulta Beauty, Liz Claiborne and Jos. A. Bank joined the store directory.

Since the turn of the century, new stores have come to WINTER PARK VILLAGE as older ones have closed. The Albertsons supermarket morphed into a Publix in late 2008. Borders Books was shuttered in late 2011. The building was demolished in August 2013 and replaced with two freestanding structures; one housing Chase Bank, the other Starbuck's Coffee and Versona Accessories.

Chamberlin's Market & Cafe, which dated back to the early days of WINTER PARK MALL, closed in May 2016. The building was demolished in June 2016, with a 1-level (25,000 square foot) REI [Sports Equipment International] opening in the spring of 2017.


The St. Petersburg Times
The Orlando Sentinel
Malls of America Blogspot / Keith Milford webmaster (State Library and Archives of Florida)
Orange Country, Florida property tax assessor website (Winter Park Magazine)