The three-bedroom home at 45 Pleasant Avenue, East Lindfield is being marketed by Ray White Upper North Shore sales agent Jessica Cao and will go to auction at 9am.
Designed in 1965 by Australian architect Kevin Winterbottom as his own family residence, the light-filled home has been held by only three families.
For the past 49 years, it has been cherished by owners Brian and Marilyn Orr, who are now preparing for their next chapter - downsizing to a retirement village less than a kilometre down the hill.
“When we first moved here, we went from being the youngest couple in the street to eventually becoming the oldest,” Mrs Orr said.
“We’ve brought up two daughters and four grandkids here, and they all went to school in East Lindfield. It has been a wonderful, warm neighbourhood to raise a family.”
Embracing its private bushland setting, the home’s design reflects an enduring open-plan approach to living.
High raked ceilings, clerestory windows for natural airflow, and rich Western Red Cedar accents frame bright, expansive interiors.
At the heart of the layout is an open-plan kitchen and dining space with a stone-topped island, and walk-in pantry.
“Our favourite part of the home is definitely the living area at the back,” Mrs Orr said.
“It’s so bright with all the windows. You look out through the wide glass sliding doors across to the paved patio and the swimming pool, surrounded by the trees.
“We see a lot of native birds back there - it's just a peaceful, beautiful spot.”
She said outdoors, a paved entertaining zone with a wisteria-draped pergola overlooks an in-ground pool equipped with a new safety fence.
Additional highlights include a tandem carport under the roofline with loft storage and a workshop, and a garden shed.
Positioned on a generous lot set well back from a quiet street, the home is close to amenities.