Full retreat: A closer look at the most enviable estates in Bowral

The ultra-prime estates of the Southern Highlands, 90 minutes south-west of Sydney, are among the most desirable and closely held country properties in Australia. Two of the region’s top agents, James Hall of Christie’s International Real Estate and Samuel Lindsay of Drew Lindsay Sotheby’s International Realty, talk us through the market—and its most sought-after addresses.

Explore luxury properties in the Southern Highlands

The appeal of acreage, and who is buying

Hall identifies two kinds of buyers. One seeks 100 acres or more, often for livestock and the potential tax benefits associated with primary production. The other prefers five to 30 acres, offering room for children and grandchildren to ride horses or motorbikes while still making it easier to manage as a country retreat.

The Boronia Street residence in Bowral, with generous decking and a self-contained pool house (top), surrounded by treetops and views towards Mount Gibraltar.

In both cases, the home remains central to the purchase. “The size of the home is important as the properties are normally an escape for family members to come together,” Hall says. Tennis courts, swimming pools, and machinery sheds are also high on buyers’ wish lists.

Hall says buyers are typically families from Sydney’s Eastern Suburbs and Lower North Shore seeking a second home, with a smaller segment interested in larger landholdings. Lindsay sees a broader mix. He says most buyers are local or based in Sydney, followed by national and then international clients.

A hilltop estate by Tina Tziallas in Mittagong.

Neither agent considers international buyers a significant force in the region. “Not particularly in the Southern Highlands,” Hall says. Lindsay notes that international buyers make up a smaller percentage of his clients than local or Sydney buyers who are “usually those weekenders that turn into primary residences.”

Limited supply, selective demands

Supply remains a defining feature of the Southern Highlands’ ultra-prime market. Hall says, “The ultra-prime properties are tightly held and generally trade quickly if they come to market.”

The treetops view of Bowral to Mount Gibraltar seen from the living area of a Boronia country residence.

Although more properties have been listed this year than last, giving buyers more choice, the selection of high-quality estates remains limited. Finding a property that meets every buyer’s requirement can still be challenging.

Where the market is heading

While activity varies across the market, well-priced properties continue to sell. Hall reports healthy enquiry levels across his listings and expects this to continue over the next 12 months.

Lindsay describes conditions as less consistent. “The market has been patchy, and it’s generally a good time to buy,” he says. He anticipates an improvement over the same period, particularly for properties in top condition with views, arable land, and proximity to Bowral.

“The Katon House”: A modern glass house by David Katon, set amid gardens with views across Fitzroy Falls Reservoir in Wildes Meadow.

As for the most sought-after addresses, Hall points to Kangaloon, streets overlooking Wingecarribee Reservoir, Range Road in Mittagong, Oldbury Road in Sutton Forest, and smaller blocks in Burradoo. Lindsay also identifies Glenquarry as an area of interest.

Read next:

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In brief: Southern Highlands’s ultra-prime property market

The Southern Highlands: A region of rolling hills about 90 minutes south-west of Sydney, including Bowral, Mittagong, Sutton Forest, and Kangaloon. Estates run from 100 acres or more for primary-producing land to country retreats of five to 30 acres.

The market: Ultra-prime listings are scarce, and well-priced properties generally trade quickly when they come to market. Most buyers are local or from Sydney, with families from the Eastern Suburbs and Lower North Shore seeking secondary residences.

The most sought-after areas: Glenquarry, Kangaloon, streets with views over Wingecarribee Reservoir, Range Road in Mittagong, Oldbury Road in Sutton Forest, and smaller blocks in Burradoo.

What’s changing: Lindsay expects the market to lift over the next 12 months, particularly for properties in top condition, with views, arable land, and proximity to Bowral.