Cintra, 34 Regent Street, Maitland selling for first time in 104 years

Heritage-listed Cintra, at 34 Regent Street, Maitland was built in 1879 for the prominent Cohen and Levy families.

It has changed hands just once in 142 years and four generations of the Long family have owned the home since 1917.

Tom Long, who lives in the house with his elder brother and sister, said the time was right to pass on the historic property to new custodians.

"We could keep it going, but in 10 years' time we're going to be in the same position in the house so we thought we'd do it sooner than later," he said.

Boasting 30-plus rooms, four-metre high ceilings and 5500 square metres of stunning grounds, Cintra is considered a rare example of an intact boom-era Italianate villa.

It has 10 bedrooms and five bathrooms across a mammoth 965 square metre footprint, and a number of outdoor buildings including original stables.

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Its listing comes just months after 47 Regent Street, situated directly opposite, set a new suburb record of $1.85 million.

The heritage-listed property known as Azuma was built as a wedding gift for the Cohen family's daughter in 1892.

Expectations for Cintra, which is undergoing a meticulous restoration, are in the vicinity of $4 million.

"It's 'the' street," said selling agent Ray Armstrong, of Jessup Armstrong.

"People think of quality in Maitland, [they think of] Regent Street.

"The further down the track we get as far as the restoration, the more interest we're getting."

Mr Armstrong said the property would be an ideal wedding venue, and had previously been used as a guest house.

"We're looking for a very specific buyer and there are those buyers around," he said.

"There's people looking at it from a gallery point of view, from a hatted restaurant point of view, an Airbnb or a guest house.

"The people we're getting are people that have had this journey before ... [they've experienced] different degrees of restoration."

The property is named after Sintra, the Portuguese village where "the Cohen families fell in love".

That love was the inspiration for the heart-shaped carriageway at the home's entrance, and the same symbol is echoed throughout the property from the chimney pots to the horse trough.

The carriageway's centrepiece, a Cupid statue, is Mr Long's contribution to the tradition of love.

It pays tribute to his late mother, who "could light up a dark room".

"I bought the Brescia marble from Florence in Italy and the Cupid to signify that," he said.

"And also pass on to another generation the love that existed here."

That generation appears to be coming soon, and Cintra almost certainly has more love to give.

Mr Long said he was unsure what emotions he would feel when it came time to part with the property.

"It'd be lovely to see someone with [interest in its history] carry it on," Mr Long said.

"As I do more and more work ... you love to see it restored and you get immense satisfaction that it's being done correctly.

"[But at the moment] you have a house that only a couple of people live in and you have to lock rooms up because they're not being used.

"It has to be used - it's a house to be used and loved."

Cintra was built for the Cohen and Levy families, who were trade merchants with stores in Maitland and Newcastle.

The property was designed and constructed by Maitland architect J.W. Pender, who also completed its only extension in 1887.

When the Cohen family dispersed from the area around 1917, five Long sisters took over the property as their three brothers went off to war.

The sisters operated the property as a private hospital for about 20 years, during which time a tennis court was established on the property's northern lawn.

Two-time Melbourne Cup winner Peter Pan was reportedly stabled at the property on his way to the cup in the 1930s.

Cintra attained heritage listing in 2012.