The original facility was the first enclosed shopping mall in Greater Boston upon opening in 1966; it was demolished and replaced by a larger building in 1994 and expanded in 2007.

The original Natick Mall was developed by businessmen William Lane, Stephen Mugar, and John Brennan.

Construction began in 1965, connecting two stand-alone locations of Sears and Filene's (which had opened in March and August 1965, respectively), with a 600,000-square-foot (56,000-square-meter), single-level shopping venue with 30 in-line stores.

It was dedicated on April 27, 1966, with two smaller anchors on the north end of the mall, Woolworth's, Pray's Furniture, and a large fountain/entertainment area in front of Sears.

Other charter tenants included Thom McAn, Baker Shoes, Ann Taylor, Parklane Hosiery, and a Hot Shoppes Cafeteria (later a York Steak House).

Weiner & Associates and William Finard, and, aside from the conversion of the former Boston Baby wing, the overall facility and retail mix had been virtually unchanged since opening in 1966.

Weiner and Finard proposed an expansion of the mall, which would include the addition of a Lord & Taylor anchor as well as a second level of retail.

However, not enough capital could be raised, and, coupled with lawsuits with Shopper's World owner Melvin Simon (who had made a controversial redevelopment proposal of that mall), the project was suspended indefinitely.

In 1992, the Homart Development Company purchased the Natick Mall and the adjacent Shopper's World in Framingham for redevelopment.

Construction of a Crate & Barrel, a relocated California Pizza Kitchen, and an American Girl Boutique and Bistro began in April 2008, with an original completion time frame of early spring 2009.

[9] The southwest mall entrance was moved approximately 100 ft (30 m), placing it between Crate & Barrel and the California Pizza Kitchen, across from the northwest wing housing J. C. Penney.

The final phase is the proposed addition of a ten to twelve story luxury hotel adjacent to the new wing and across from J. C. Penney.

Real estate agents in the Metrowest area stated that the prices of the units, ranging from $379,900 to over $1 million, combined with the timing of the opening of the facility have harmed sales.

[15][16] This was discussed by analysts as following suit with the "emerging trend" of nontraditional anchors in order to "emphasize experiences and fun over shopping".

Each gaming experience will be categorized by their design elements, such as Aztec Temple, Space Void, Apocalypse, Pirates, Magician, Rainforest and Mansion.

On August 27, 2020, Lord & Taylor announced they would be retiring their traditional brick-and-mortar division after modernizing into a single digital collective outpost.

[34] The exterior of the Neiman Marcus location is covered by 80-foot (24 m) curved stainless steel panels colored in various shades of brown; it is intended to resemble a woman's dress.

[35] Homart Development Corporation (then a division of Sears) was acquired by General Growth Properties (GGP) in December 1995, at which time the Natick Mall was valued at $265 million.