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The Woollahra Hotel: Built in 1831, the Woollahra Hotel is one of the suburb’s oldest landmarks and continues to be a popular gathering spot. Originally a coaching inn, it played a significant role in the early development of the area.

 A key historical site is All Saints Church on Ocean Street, designed by Edmund Blacket built between 1874 and 1881.

Woollahra is an inner-eastern suburb known for its tree-lined streets, heritage buildings, and a village-style commercial centre that has largely remained untouched by major development. Together with neighbouring Paddington, Woollahra boasts one of the highest concentrations of art galleries in Sydney. The area also offers an array of cafes, restaurants, and antique shops, especially around Queen Street.

Green spaces such as Harbourview Park, Plumb Reserve, and Cooper Park provide ample room for outdoor activities. In addition, Edgecliff Road is lined with charming cafes and boutiques, further enhancing the suburb's appeal.

Woollahra is regarded as a prestigious and affluent suburb. Woollahra shares borders with Paddington, Double Bay, Bellevue Hill, Bondi, and Bondi Junction. Though it is within walking distance to Double Bay, Bondi Junction, and Queen Street, the suburb retains a sense of being tucked away and secluded. Notable streets in the area include Attunga Road, Edward Street, View Street, Fletcher Street, Wallaroy Road, and Weeroona Avenue.. Since 1908, it has been represented by the Sydney Roosters in the National Rugby League (NRL), also known as the Eastern Suburbs District Rugby League Football Club.

The suburb hosts several government consulates, including those of Serbia, Russia, Poland, and Turkey.