1954 - On June 23, the Oakville Trafalgar Real Estate Board is established and consists of 41 members and one staff (secretary). The Board's office is located on Colborne Street West (Lakeshore Road today). Bill Davis, a founding member, is elected as the Board's inaugural President. Wednesday afternoon was a half-holiday during this time.
1959 - Following a fire at the office which destroyed the Board's records and correspondence, a new office is opened at 334 Colborne Street East in Oakville. Gross co-operative sales total $2,101,000.
1962 - Margaret Paul is elected as the Board's first woman President. Gross co-operative sales total $4,227,153.
1964 - The Board moves to a "spacious" new premise, occupying the second floor of the former Record-Star (newspaper) building on Church street, west of Thomas. The Board consists of 74 members. Notices of new listings and sales are distributed in town by mail.
1965 - Gross co-operative sales total $6,648,475
1968 - Over $10 million dollars in gross co-operative sales.
1969 - The Board purchases the home/office at 152 Trafalgar Road for $39,000 from a plumber, who was soon-to-be mayor, and a lawyer.
1974 - The Board moves to the office space it owns on Trafalgar Road. Membership consists of 250. In February, the average residential home in Oakville sold for $52,000.
1975 - The total dollar value of multiple listings totaled $74 million.
1979 - The Board publishes its first computer-generated (MLS) catalogue. An addition is constructed onto the Board office building on Trafalgar Road.
1981 - The Board raise $35,000 for Dave Hawkins, a 17-year-old hockey player for the Oakville Blades who is paralyzed from the chest down following an accident during a hockey game in September 1980. The money goes towards renovations and modifications of the Hawkins' home.
1982 - OMDREB becomes the second Board in Ontario to become fully computerized (MLS).
1983 - OMDREB consists of 418 members. The average sale price of a home in Oakville is $95,000.
1986 - Part-time sales agents are denied membership. Years later, this decision is struck down.
1989 - OMDREB consists of 747 members. The average sale price of a home in Oakville is $237,500.
1993 - OMDREB signs its first mutual access agreement with the Metropolitan Hamilton Real Estate Board or the Real Estate Association of Hamilton-Burlington (RAHB), as it's known today. OMDREB sells its office on Trafalgar Road, relocating to its current location on Navy Street in August 1994.
1994 - Board staff consists of four full-time staff and two part-time administrators. Over $500 million in gross co-operative sales.
1996 - OMDREB consists of 505 Members.
2004 - OMDREB celebrates its 50th anniversary. Bill Davis, founding President who passed away in 2001, is honoured with "Bill's Bench," a memorial bench located outside of the Board's office on Navy street. "Every Day Above Ground is a Good Day."
2015 - OMDREB along with six other real estate associations launched the Regional Matrix System with CoreLogic. The Regional group consists of the Oakville-Milton, Kitchener-Waterloo, Cambridge, Simcoe, Niagara and Guelph.
2017 - OMDREB consists of over 1,800 Members and Board employs 14 staff.