Chester St, Woollahra NSW 2025
Chester St, Woolloahra NSW 2025 is a local road where 25% of homes are houses and 53% are apartments. 10 homes sit above the street; 4 homes sit below the street. There are insufficient recent house sales to calculate a reliable comparison against the suburb, so buyers should compare recent sales of individual homes on the street against nearby comparable properties. The street features apartment developments at 16 Chester St (8 lots, 4 levels), 14 Chester St (6 lots, 4 levels, built 1975), and 18 Chester St (6 lots, 3 levels, built 1969). House turnover over 5 years is 11.8%, while apartment turnover is 22.2%.
The mix of houses and apartments (units) that make up the Chester St, Woollahra NSW 2025 property market.
"Houses" in this report includes detached houses, duplexes, and terraces.
How house lots on Chester St, Woollahra NSW 2025 sit relative to street level — topography that affects drainage, flood risk, privacy, and build cost. Statistics are calculated from properties with available data.
See which key planning overlays and environmental risks affect this street before you buy.
Actual house sales on Chester St, Woollahra NSW 2025 over the past 5 years, plotted against the Woollahra NSW 2025 median house price trend over the same period.
Actual apartment (unit) sales on Chester St, Woollahra NSW 2025 over the past 5 years, plotted against the Woollahra NSW 2025 median apartment price trend over the same period.
The largest apartment projects on Chester St, Woollahra NSW 2025, ranked by number of lots.
2 popular apartments on Chester St, Woollahra NSW 2025
Get the knest.ai app
Gain ultimate insights into any property
Buyer-focused property platform identifying risks, price estimates, 3D land maps and more to help you make smarter decisions — completely free.

Common questions about living on and buying property on Chester St, Woollahra NSW 2025 — lifestyle, transport, and the local housing market.
Note: Data is sourced from the Australian Bureau of Statistics (ABS) 2021 Census data and knest.ai internal statistical data.
Is Chester St an expensive or affordable street relative to Woollahra?
There are insufficient recent house sales on Chester St to calculate a reliable premium or discount against the Woollahra average. Buyers should compare recent sales of individual homes on the street against nearby comparable properties to gauge current market positioning.
What are the risk and overlay factors on Chester St?
There are no bushfire, heritage, or high-voltage overlays on Chester St. No properties fall within a flood overlay, and no homes are recommended for a flood check. However, 17 properties fall under other flood classifications, meaning no flood risk was identified or the property was not mapped. This does not indicate a flood risk, but reviewing council mapping and insurance costs before purchasing is always prudent.
Are properties on Chester St mostly on high, level or low ground?
10 homes sit above the street; 4 homes sit below the street. Different site heights relative to the street can influence site characteristics, but buyers should assess the specific property rather than relying on the street average.
What type of road is Chester St?
Chester St is a local road. Local roads generally serve nearby residents and connect directly to collector roads, rather than carrying significant through traffic. This classification typically suggests a quieter environment focused on local access, though buyers should verify specific traffic conditions during their inspections.
Is Chester St mostly houses or apartments?
There are 68 residential properties on Chester St. Houses make up 25% of the stock, while apartments account for 52.9%. The street features a mixed profile of dwelling types rather than being predominantly one category.
What are the major apartment developments on Chester St?
The major apartment developments on Chester St include 16 Chester St with 8 lots across 4 levels, 14 Chester St with 6 lots across 4 levels built in 1975, and 18 Chester St with 6 lots across 3 levels built in 1969. These developments contribute to the street's higher-density residential character.
How many properties have sold on Chester St?
No houses or apartments have sold on Chester St in the past 12 months. The 5-year turnover rate for houses is 11.8%, and for apartments, it is 22.2%. Turnover measures the proportion of properties that changed ownership during the past five years.
Is Chester St a good street to buy property on?
Chester St may suit buyers seeking a local-road residential environment with a mix of detached homes and apartment blocks. The street offers 10 homes sitting above the street and 4 sitting below, alongside three established apartment developments. With no bushfire, heritage, or high-voltage overlays, it presents a straightforward purchase for those comfortable with the current turnover rates and mixed housing stock.
73 Nearby Streets in Woollahra, NSW 2025