Pennydale is a neighbourhood in the suburb of Cheltenham in Melbourne, Victoria, Australia, approximately 17 km south-east of the Melbourne central business district. Pennydale lies within Cheltenham between Bay Road to the north, Jack Road to the west, Park Road to the south, and the Frankston railway line to the east. It is entirely within the local government area of the City of Bayside.

Pennydale is named after the Penny family who moved to the area in 1852, combined with the suffix "dale" meaning valley, as it was “sheltered by hills the same as in the old country”, referring to England. In particular the name recognises Edwin Thomas Penny (1848–1916), who was 4 years old when his family migrated. Penny was known for his many community activities including:

On 9 December 1916 Penny unexpectedly died. An official report stated his cause of death as shock, cardiac syncope, and internal ruptures. He was buried at Cheltenham Cemetery on 11 December. After his death, the name Pennydale continued to be used colloquially.

The first official usage of “Pennydale” was in 1956 when a post office was established in the Bay Road East Shopping Centre. The post office was opened to avoid confusion in deliveries between the Cheltenham and the Highett Post Offices. The official postal address at that time was "Pennydale S22". When the system changed to post codes, Pennydale used the same Post Code as Cheltenham of 3192. The post office closed in 1999. Although no longer correct, letters addressed to Pennydale 3192 may still be delivered.

In 2006, the previously unnamed park in Olympic Avenue was named Pennydale Park by Bayside Council. In 2022, the Victorian State Government gazetted the neighbourhood name "Pennydale" as an official neighbourhood in Cheltenham.

Olympic Avenue Kindergarten is located in Olympic Avenue. It opened in 1955 as the Olympic Avenue Play Centre before changing to a Kindergarten in 1958.

Along its east border Pennydale is served by Southland railway station and Cheltenham railway station on the Frankston line. In 2018 the Labor State Government announced the Suburban Rail Loop with the first phase starting in Cheltenham and finishing in Box Hill. The SRL Cheltenham station will sit in Sir William Fry Reserve, adjacent to the north-eastern corner of Pennydale, with a planned opening in 2035.

Pennydale is served by bus route 822 (Chadstone Shopping Centre to Sandringham via Murrumbeena and Southland Shopping Centre), and route 828 (Hampton to Berwick Station via Southland Shopping Centre and Dandenong).

The two parks located in Pennydale are:

• Pennydale Park
• Tulip Grove Park

• Cheltenham, Victoria
• City of Bayside