An attempt by Donald Trump to slash the property tax bill on a golf club outside New York City may be undermined by records indicating that he previously said the property was worth 35 times more than the value he is now trying to convince a judge to approve.

The Republican presidential frontrunner is suing the town of Ossining in Westchester County to reduce the taxes on Trump National Golf Club, a 147-acre property with a lavish clubhouse and 18-hole course whose managers are separately accused of causing floods that led to $240,000 worth of damage to local public facilities.

Donald Trump bought the Briarcliff Manor golf course at foreclosure for about $8m in the mid-1990s. Photograph: Robert Kalfus/Splash News

Trump’s lawsuit in county court argues that the luxurious private club, which he bought in foreclosure for about $8m in the mid-1990s before spending what he claimed at the club’s opening event was another $45m in improvements, has been unfairly assessed and is in fact worth only $1.4m.

“That is crazy low,” Fernando Gonzalez, the Ossining town assessor, said in an interview. Town authorities are fighting back against the allegations. “We believe they do not have a case,” said Gonzalez. Attorneys for Trump did not respond to questions.

Trump’s new valuation, however, contrasts with the 92-page financial disclosure document that he released to the US government as he embarked on his audacious campaign for the presidency last year. Trump listed the Westchester club and its manicured links as an asset worth more than $50m within his purported $10bn fortune. The club charges would-be members an $250,000 entry fee.

If his legal bid were successful, Trump’s club would reduce its town tax bill – which goes towards schools and other local services – by 90% or $424,176 per year. The billionaire’s gambit has infuriated some of the community’s less wealthy residents. “He should be made to pay it,” said Thomasina Laidley Brown, the chair of the local Democratic party. “We, the people that live here, don’t get any special favours, and I don’t think he should.”

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Trump’s lawsuit is only his latest disagreement with members of the community in Ossining and its sleepy village of Briarcliff Manor, where the golf club is located. Magnificent homes line leafy winding roads that are quiet except for the scuttling of squirrels. Many wealthy residents follow the same 45-minute commute south into Manhattan’s Grand Central station made by Donald Draper in the early seasons of the TV drama Mad Men.

The Trump property also features a series of gleaming condominiums and villas overlooking the fairways, whose owners are also fighting to lower their tax bills. Trump owns a mansion and 230-acre estate about 12 miles to the east of the golf club. Roughly in between the two properties is the house in Chappaqua where Hillary Clinton, the former secretary of state who is increasingly likely to face Trump in November’s general election as the Democratic nominee, maintained a private email server that is now under investigation by the FBI.

But one day a few years ago, the picture-postcard scene was spoiled. Amid heavy rains over the Lower Hudson Valley, the village library, public pool, children’s playing fields and other amenities were badly flooded. And village authorities lay the blame at the feet of Trump, who these days is the surprise frontrunner for the Republican presidential nomination.

In a separate lawsuit against three Trump companies now being fought in the county court, lawyers for Briarcliff Manor allege that Trump’s golf club managers made “illegal and intentional modifications” to their drainage systems that resulted in the rest of the village suffering a deluge in June 2011.

Flooding in the village of Briarcliff, caused by water run off from the Trump National Golf Club at Briarcliff, Westchester County. Photograph: Westchester County clerk

In court filings, the village alleges that they were swamped by stormwater after more than five inches of rain fell on the golf course and surrounding area. They say the alterations by Trump managers increased the rate at which water ran off the Trump property.

Poor maintenance of the Trump system also caused debris such as boulders and branches to flow from the golf course into the village drains, it is alleged, causing a blockage so severe that a manhole in the village playing fields burst open and “became a geyser spewing water”.

The alterations were made “to improve aesthetic golf course quality and golf-play”, according to the village authorities, who are demanding more than $238,000 from Trump to pay for the damage they say was caused. “It stopped people from using the facilities,” said Georgina Gualdino, the chair of the village’s recreation advisory committee. “Everything had to close for a week or more while everything was cleaned out.”

Flooding in the village of Briarcliff. Photograph: Westchester County clerk

In typically combative style, Trump does not merely deny the allegations, but also claims that they are a vehicle for professional revenge against him.

Eight months after the storms struck the village, Trump was selected by New York City to take over the development of a separate taxpayer-funded golf course, which was years behind schedule and millions of dollars over budget. The contractor that Trump took over from was owned by William Vescio – who also happened to be the mayor of Briarcliff Manor.

Trump claims that Vescio orchestrated the village’s flooding lawsuit against him as retaliation because Trump criticises his firm’s work on the public golf course as a “glaring example of taxpayer waste”. Vescio and the village manager, Phil Zegarelli, declined to comment.

The Republican candidate’s legal team is bullish. “We feel very strongly that we are in the right,” Alan Garten, an attorney for Trump. Garten has obtained in proceedings an internal email in which Vescio concedes that the flooding was caused by the scale of a “100-year storm” and “we cannot hold Trump responsible for that.”

Trump was scheduled to give a sworn deposition on his claims of revenge in July last year, but the appointment was cancelled after he announced his campaign for the White House. Village attorneys again demanded last month to interview Trump, but Trump’s lawyers appear to be opposed to this. Both lawsuits remain ongoing in the Westchester county court.

The dispute is not the first time that Trump, 69, has been accused of failing to pay his fair share. Just this week, New York City also asked him to give back a $300 annual tax discount for residents earning less than $500,000, which Trump appears to have been receiving in error and which he has not indicated whether or not he will return. “Maybe $300 on other people’s taxes is a big deal, but not on his,” said Trump’s campaign manager Corey Lewandowski, who said that his boss had applied for the tax break before an income cap was introduced. Trump has so far resisted pressure to release his personal income tax returns, as past candidates have done.

Trump National Golf Club has created controversy ever since its inception. Trump caused a commotion by arriving in a garish stretch limousine for a hearing of the village planning board that considered his plans in 1999.

Richard Mattiaccio, an attorney and friend of supreme court justice Sonia Sotomayor who then lived in the village, was recruited to run a last-minute campaign for mayor to unseat the incumbent and block Trump’s plans, which he recalled as “too large, too ambitious for the space”.

Emotions and turnout ran so high, he said, that a woman was arrested for remonstrating with a police officer who tried to stop her entering the voting station seconds after polls closed. Ultimately the effort fell short. “Quite a number of the residents were starstruck,” Mattiaccio recalled this week.

These days, however, views on Trump appear to have mellowed somewhat in the area, which voted solidly in favour of Barack Obama’s re-election in 2012 and is represented by liberal Democrat Nita Lowey in the House of Representatives. Residents said they barely saw the Republican frontrunner.

Gayle Waxenberg, a former elected trustee of the village, said the Trump organisation frequently donated rounds of golf for educational charity auctions held in the clubhouse banqueting hall. Once when he was passing through, Trump got up onstage and urged guests to dig deep. “I never saw Trump as anything other than a good neighbour,” said Waxenberg, who recently moved out.

Others quietly voiced their disgust for Trump’s nativist campaign, which has centred around a pledge to build a wall along the southern US border and make Mexico pay for it. Miguel, an Ecuadorian waiter in one of Briarcliff Manor’s restaurants who did not give his last name because he was not authorised to speak to the press, said he doubted Trump could win over the country’s newcomers by being so brash. “He is just so rude,” said Miguel. “How do you talk to people like that?”