A rain tree fell on four-storey walkup condominium Kismis Court in Toh Yi Road, damaging at least three units and two cars.
No one was hurt in the incident that happened on Monday at about 10pm.
The owners of one of the damaged units on the third storey told The Straits Times they were woken up by a loud crash.
Mr Alan Woo, 78, and his wife Ellen, 76, got out of bed, drew their curtains and were shocked to see a fallen branch pressing against their closed window.
Residents said the tree was at least 50 years old and it was taller than their four-storey block.
Speaking about the ordeal from their unit, Mr Woo, a retired businessman, said yesterday: "It was so loud; it sounded like a plane dropped out of the sky and crashed into the building."
He and his wife, a retired teacher, have been living at Kismis Court, which is off Bukit Timah Road, for nearly 40 years.
The railing of their balcony was bent by the tree. The couple hope either the condominium's insurance or their home insurance will cover the cost of damage. Their car, which was parked next to the block in the compound, was also damaged.
Another affected unit on the ground floor suffered more extensive damage.
The occupant of that unit, a retired businesswoman who wished to be known only as Madam Fu, 84, showed ST how the garden was completely covered by the tree's branches, fallen roof tiles and shattered glass. She also indicated the retractable awning that once sheltered her patio, now ripped off by the fallen tree.
One of her windows had also been smashed.
Workers from a landscaping company were using chainsaws to cut and remove branches.
Madam Fu, whose home is covered by home insurance, said it was not raining but it was slightly windy when she returned from a wake and saw neighbours gathered outside.
"(The electricity) in my whole home was tripped off," she said, adding that gardening was her passion and she usually went out to garden in the evenings.
"The birds were always singing up there in the morning... It's quite a shame," she added.
Dr Geoffrey Benjamin, 80, the chairman of the council that represents residents at Kismis Court, said the tree was one of two old trees in the condominium checked by arborists every two years.
Dr Benjamin, an anthropologist, said the tree was pruned about two years ago. He added: "The residents' council will hold a meeting to discuss the issue but details of insurance and claims will be left to the management."
Insurance agents told ST that home insurance could cover the damage caused by a fallen tree since it could be considered a natural disaster.
Owners of cars damaged by fallen trees within private property can claim against their own motor insurance policy, with payout amounts dependent on the damage to the vehicle.
The damage will be verified by insurance surveyors.
While Madam Fu was grateful no one was hurt, she was sad about her 40 potted plants, which included hibiscus, basil and pandan, that were crushed by the tree.
She said: "I can't believe it. It used to be so colourful. Now, when you look outside, it's in complete ruins."