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

Greater Orlando's second enclosed shopping mall was built on a 40-acre plot, located 3.4 miles northeast of the center city, in suburban Winter Park. Enveloping approximately 528,000 leasable square feet, the complex was designed by Atlanta's Toombs, Amisano & Wells firm and developed by Jacksonville's Robert H. Jacobs, under the auspices of the S.S. Jacobs Company.

The first operational store, Walgreen Drug, began business on August 4, 1964. Five stores were dedicated on August 6th; J.B. Ivey, Bill Baer of Winter Park TV & Stereo, Elizabeth's ladies' sportswear, Matthews ladies' wear and a freestanding (28,700 square foot) Winn-Dixie supermarket.

WINTER PARK MALL was officially dedicated on August 20, 1964. The 15 million dollar complex was anchored by the 2-level (130,000 square foot), Charlotte-based J.B. Ivey, which presided over its north end. A 2-level (142,000 square foot) J.C. Penney stood on the south. The store was the J.C. Penney chain's first full-line, "New Generation" store. It brandished the brand new "Penneys" logo and featured a greatly-expanded selection of merchandise and services.

Among forty-one charter tenants were Schwobilt Clothes, Lillie Rubin ladies' wear, Claude Wolf Home Appliances, Lawton's Jewelers, Winter Park News, The Town Squire young men's shop, Toy & Hobby Chest and (25,000 square foot) F.W. Woolworth 5 & 10.

In the early years, contemporaries of WINTER PARK MALL were COLONIAL PLAZA (1956) {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, Allied Radio Shack, Schwobilt Clothes and Wig Land. Repairs were made and all effected 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 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, WINTER PARK MALL 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 built at 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 fifty-eight stores and services under its roof.

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 ORLANDO FASHION SQUARE, can now be seen as the beginning of the end for WINTER PARK MALL.

By mid-1994, the shopping center had lost twenty-five stores, with most never being replaced. The proprietor, Orlando Regional Center Associates, considered renovating and repositioning the struggling complex as an enclosed upscale fashion mall. Parisian would be signed to retenant the vacant Penneys. A new Belk-Lindsey would be built onto the east side of the structure. 

By 1996, the plan had been abandoned. A joint venture was formed with Columbus, Ohio's Don M. Casto Organization. Plans for a new 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 Firestone Auto and 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 and improved WINTER PARK VILLAGE.

Dillard's upset the apple cart when they closed their store, on August 16, 1999. The budding retail and office complex was now without a department store anchor. It was decided to section the lower level of the vacant Ivey's / Dillard's into seven inline store spaces. The upper level would be refitted with fifty-eight loft apartments.

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

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

Since then, 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, a tenant at 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 Evening Star
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)