Ten shops, cafes and restaurants on the edge of Monro Park at Cronulla have been sold for between $18 and $20 million.
The site, 138-142 Cronulla Street, occupies an entire block and is zoned B3 commercial, allowing a mixed use development of up to six storeys with shops at the bottom and apartments above.
The sale is the beginning of the end for businesses along the strip, but it could be up to two years before they close.
Business owners and patrons are saddened the quaint corner of Cronulla will be gone and have concerns for overshadowing of the park, which is particularly popular with mothers of babies and toddlers.
Commercial real estate agents Knight Frank sold the property after a six weeks' sales campaign.
Agents Richard Garland and Demi Carigliano said they could not disclose the price, but it was between $18 and $20 million.
The buyers were business partners from outside the area, who would look to develop the site in about two years once leases expired.
Mr Garland said one family had owned the block for about 50 years, and the last owner inherited it from her father.
"There is a site specific development control plan for the site, which tells you what you can and can't do," he said.
"This site will have views over Gunnamatta Bay and it's very convenient to the train station and Cronulla CBD."
Mr Garland said the real estate market in Cronulla continued to perform well.
"Cronulla is a micro market because it is highly sought after by downsizers and retirees," he said.
Anna's Shop Around the Corner is among businesses that will be affected.
Anna Loder, who has run the cafe and book shop for 11 years, said, "We don't want to see any change".
"This is the perfect place for us. We love the park and the vibe.
"Even if we were offered first refusal for a shop in the new development, it wouldn't suit my clientele or my ethos."
Allison Polkinghorne and Rhia Forsyth, who became friends at Sutherland Hospital where their babies were born seven weeks ago, were enjoying coffee at one of the cafes.
Ms Polkinghorne said the whole character of the area would change.
"That would be disappointing in one sense, but it could also have some pros," she said.
"Maybe, it would be a bit more modern, and you would get more families.
"Regardless, development is happening all around Cronulla, and that will not change."
Ms Forsythe said, "I like it the way it is, but it's the way everything in Sydney is going".