Martha’s Vineyard

The warm summer breezes and vast sandy beaches of Martha’s Vineyard have long attracted the Left-leaning American political classes to its shores during the months of July and August. It was Ulysses S. Grant who put the 23-mile-long island, which is roughly twice the size of Jersey, on the presidential-vacation map, when he visited a friend in 1874.

It later gained international notoriety after the 1969 Chappaquiddick incident in which Mary Jo Kopechne was killed when a car driven by Senator Edward Kennedy fell off the Dike Bridge. Bill Clinton and his family regularly visited during and after his presidency, and the island was once more in the international press when President Obama and his family holidayed there last August.

Unlike the more glitzy Long Island villages of the Hamptons, the Vineyard succeeds in absorbing the influx of high-profile politicians, media moguls and celebrities in summer houses tucked down anonymous sandy lanes. These properties are all about the discreet New England aesthetic: a cluster of shingle buildings buried in verdant gardens, all with the requisite panoramic views of the water. Days are played out on empty beaches and cycle rides, enjoying the novelty of pick-your-own vegetable plots and fishing for striped bass.

On the island’s eastern coast, Edgartown is scattered with shops selling preppy clothes with a sea-faring bent. ‘Up island’ (the term refers to heading up stream) or west towards the villages of West Tisbury and Chilmark there are scenes of farmhouses, meadows and dry-stone walls. It’s understated and peaceful-the sand-battered 4x4s can’t exceed the island speed limit of 20mph.

‘In comparison with city life, the Vineyard has a slower pace and is centred around a quiet lifestyle that includes the beach, boating, dining out and socialising with friends,’ explains Caroline Taylor, who sells some of the largest beach houses on the Vineyard. ‘There are gorgeous conservation properties for walking and relaxing. Many residents have been coming here for generations, and, as families expand, so do the relationships with summer friends.’

The market for prime second homes slackened dramatically during the recession in late 2008 and through-out most of 2009. ‘Then, we experienced a surge in sales before winter set in, and the prediction for 2010 is a recovering market,’ explains Mrs Taylor. ‘Although we are still relying on price reductions to cost properties realistically, sales prices are rising again in certain markets, as are the sales numbers. Our high-end and beach-home markets are strong and there are some very good buys for the investor who will renovate a property and keep it for rentals.’

Nantucket

There is a good-humoured, if slightly barbed, rivalry between Vineyarders and Nantucket islanders. The former whaling capital of the world, which is 10 miles farther out to sea to the south-east, attracts an even more affluent buyer and house prices are higher, but the reasons for this aren’t exactly clear. ‘Nantucket has long had a history as a place to get away to. Its main attraction is its physical isolation from the rest of the world, which appeals to a certain type of person,’ explains Kate Ranney Sayle of Denby Real Estate in Nan-tucket.

‘Why that translates into higher real-estate prices, I’m not sure anybody knows.’ A bonus is the tight conservation clauses placed on both architecture and the landscape: ‘The Nantucket Conservation Foundation set the trend for capturing open space and, because of this, almost two-thirds of the island remain untouched.’ Carolyn Durand of Lee Real Estate describes the island as ‘one of the rare places left on Earth where you can feel that time has been suspended’.

The Nantucket Film Festival (June 17-20; www.nantucketfilmfestival.org) draws in its fair share of Hollywood names, but, otherwise, there’s the generational pull from families who have summered here for years. ‘Socially, the island is laid back, and you feel that from the first step ashore,’ adds Mrs Durand. ‘Our summer visitors relax at the beach, read real papers rather than ones online, go to dinner in casual clothes at the nicest restaurants and escape the go-go-go of life on the mainland.’

The market has had a tough 18 months, with the fallout from Lehmans and other collapses in the financial markets taking a heavy toll: buyers and sellers have had to adjust to a new world of prices. During the boom year of 2006, the record average sale price, according to Denby Real Estate, was $2.438 million, but the number of transactions last year fell to their lowest since 1985.

In 2009, houses that did sell went for 79% of their original asking price, ‘and I think that’s a fair reflection of the market adjustment,’ adds Mrs Durand. ‘In some price tiers, the market came down 30%, and in others, it was closer to 20%, but across the island, it’s fair to say they have adjusted about 25%.’ But she sees this as a real opportunity: ‘We’re hoping the adjusted costs will bring back buyers who felt that prices had got too far away from them.’

Newport

Just to the west of Cape Cod, about 50 miles south of Boston, lies America’s smallest state, Rhode Island. It was here, in the former America’s Cup host town of Newport on the Narragansett Bay, that Jacqueline Bouvier married Senator John F. Kennedy on September 12, 1953. But Newport had long been on the glamour map for smart north-easterners: it became the resort for wealthy socialites when, in the 18th century, the likes of the Vanderbilts and the Astors built large mansions along Bellevue Avenue, and referred to them nonchalantly as ‘cottages’.

What Newport has over the Vineyard and Nantucket is direct access. ‘We see ourselves more and more competing for the same second-home buyers,’ explains Paul Leys, co-owner of Gustave White. ‘But, at the end of the day, it’s more convenient: you don’t have to deal with the Cape Cod traffic and there’s no ferry.’ Before, those who bought in Newport had a connection already, but, today, that’s not the case. ‘Whether I’m dealing with a high-net-worth individual or someone with more modest means, everyone is much more geographically flexible today than five years ago. We used to have a primarily Boston market, but, today, buyers are coming from all over.’

Newport is more of a year-round destination than the Cape Cod islands, which, in the middle of February, are like ‘ghost towns’. But one downside is that finding a house with a garden that leads onto the beach is hard. ‘If they’re on the water’s edge, you can swim, but it’s often rocky,’ explains Mr Leys. ‘People tend to go to the public beaches instead.’

The upside is that the market has something for everyone, with houses ranging from classic Portsmouth cottages for $300,000 to opulent estates at $20 million. The market also seems to be in better shape. ‘We have seen a marked increase in interest and sales activity in the first quarter of 2010,’ reports Melanie Delman of Lila Delman Real Estate. ‘The consumers we encounter are value orientated and properties are trading at great prices.’