A line of 96 trees along Gannons Road, Caringbah, will be cut down so a shared cycle-walk path can be extended.
Sutherland Shire Council says 300 new trees - three for every one removed - have already been planted inside the adjacent Woolooware Golf Course.
The three-metre shared path is due to be built early this year along Gannons Road from Denman Avenue to Captain Cook Drive.
The line of trees is highly valued by the community, given the outrage when they were savagely pruned by Ausgrid in 2016 to prevent them affecting power lines.
A council spokeswoman said the trees, which were planted below power lines during the early 1980s, had suffered regular hard pruning and an arborist assessment also found that many had decay in their trunks and limbs as a result of the continued pruning.
"The trees are now being removed to accommodate the shared pathway being constructed," she said.
"Offset planting was completed in 2016, allowing several years for establishment prior to any removal.
"The upgrade works along Gannons Road between Captain Cook Drive and Denman Ave will provide an important north/south link between the existing Woolooware Bay shared pathway network and the proposed Sutherland to Cronulla Active Transport Link.
"As this area also sees a significant number of school students, sporting field users and sports enthusiasts utilising the existing footpath as a route to their destination throughout the year, the new shared pathway will create a safer experience for pedestrians and cyclists within this road corridor.
"The path upgrade forms part of council's ongoing commitment to providing a comprehensive bicycle network throughout Sutherland Shire.
"Council also recently celebrated a milestone of 10,000 trees planted as part of its Green Streets Program."
A council project statement said, for every tree to be removed, three new trees had already been planted within the adjacent golf course.
"The removal of street trees was anticipated in April 2016, as they had been planted beneath the overhead electricity wires during the early 1980s," the statement said.
"To maintain the required clearance between the electricity lines and the tree canopy, they have suffered regular hard pruning by the electricity authority for many years, and do not contribute greatly to the streetscape or the environment.
"Extensive replacement planting has already been undertaken nearby within the golf course, using more appropriate species that will have a long-term positive environmental impact.
"The 300 new trees include Casuarinas, Eucalyptus and Melaleucas species, which are being monitored.
"Only trees on the eastern side of the road are affected."
The new boundary fence along the golf course frontage will have a finer grade mesh to prevent golf balls passing through.
