After suffering a series of reverses.she has sold the Beanscene coffee bar chain and the upmarket Fifi and Ally business based in Glasgow's Princes Square to leisure trade veteran Stuart Mckenzie.
Ms Hamilton said the value of the deal was confidential and that Newton Mearns-based Mr Mckenzie was one of a number of bidders.
The 50-year-old property expert said she felt some sadness to leave the businesses but the decision to sell reflected her belief it was time to pass them on to someone who could take them to the next stage.
She added: "It's the right time for me to make that decision in my life."
The sale is a low-key departure from operations Ms Hamilton moved into amid some fanfare.
A successful surveyor, Ms Hamilton launched the Fifi and Ally venture with her cousin Alison Fielding in 2005 to try to tempt consumers with a mix of designer fashions and homewares sold alongside a smart cafe.
She expected the first outlet in Glasgow would provide a model for other UK stores but did not open outside the city.
The business has one cafe outlet and stopped selling fashion items some years ago.
Beanscene has 10 outlets in Scotland.
Months after she bought the then 12-strong chain out of administration in 2008, Ms Hamilton talked about doubling the number of stores.
Asked if people might feel that she had failed she said: "Maybe some people will say that but I don't think so. When I took the company on I was not expecting the economic situation we were going into."
The acquisition of Beanscene came as the global economy plunged into a deep downturn that lasted much longer than anyone expected. This put consumer spending under pressure for years.
Beanscene faces competition from well-funded giants like Starbucks and Costa.
Ms Hamilton said the problems in the banking sector also created challenges. She said: "To get funding for the vision I had it's a very, very difficult market."
She added: "I did not have bottomless pockets, I did as much as I could."
But Ms Hamilton said the businesses achieved much amid challenging conditions. "What I am proud about is we have not lost any staff. The company is still here. That's more than a lot can say."
She noted Mr Mckenzie had plans to grow the business.
As head of transport, airport and global infrastructure at the Jones Lang LaSalle surveying business, Ms Hamilton's job involves lots of overseas travel.
In 2011 Ms Hamilton said she had lost £1million following the closure of a second Fifi and Ally outlet on the city's Wellington Street.
The venue closed following objections from a neighbouring tenant about noise in the evenings.
Ms Fielding left Fifi and Ally in 2009.
The last accounts filed by Beanscene Scotland show it had accumulated £171,000 losses at 31 December 2012.
In them Beanscene Scotland says: "The accounts have been prepared on a going concern basis due to the company having the continued support of its director."
The accounts say the company issued £150,000 shares in the year and further capital was introduced into the business post year end.
In 2011 Ms Hamilton said the results of Fifi and Ally would be included in those of the Beanscene business.
Mr Mckenzie, 63, could not be contacted yesterday.