Homer’s Pond, a vast private estate on Martha’s Vineyard, is one of the most expensive listings in the United States.

At a time when the economy is resurgent and there is confidence that the clouds of crisis are clearing, it seems only fitting that a once-in-a-lifetime home should come to market. To purchase this unique property, however, you may need to be a Wall Street financier or a dot.com billionaire because Homer’s Pond is an exercise in superlatives.

An exceptional 314-acre oceanfront estate on the south shore of Martha’s Vineyard, just off the coast of Cape Cod in Massachusetts, this rare and exclusive island retreat is one of the largest coastal properties for sale in the U.S. northeast.

With 1,200 feet of private waterfront, a 35-acre freshwater pond for swimming and boating, and a vast swathe of pristine woodland and grassland, this award- winning 5,600-square-foot home also boasts a state- of-the-art wine cellar with room for 12,000 bottles, and floor-to-ceiling windows delivering expansive island and ocean views.

But perhaps the greatest superlative is the price tag. At $118 million, Homer’s Pond is one of the most expensive houses in America, and a member of an exclusive club of $100 million+ homes currently on the market.

Located in West Tisbury and less than seven miles from historic Edgartown – a former whaling port where renovated ‘Captain’s homes’ line the harbor on Water Street – Homer’s Pond is just 10 minutes from the island’s airport. Direct flights to New York take only an hour and to Boston some 37 minutes, but the property’s privacy and tranquility set it a world apart.

And that’s the beauty of it. Surrounded by ocean and conservation land, the property’s size and seclusion are a rare find. Indeed, the extent of the property can only really be appreciated from above.

“Homer’s Pond is so large and secluded that one might call it a private kingdom,” notes Charles Carlson of South Light Property, the listing agents. “The unique size and terrain maximize privacy. Its proximity to the airport ensures quick access, and for those looking for an active lifestyle, Edgartown is minutes away. Homer’s Pond is much more than a summer escape, it is a year- round investment.”

The elegant main residence overlooks Little Homer’s Pond, the smaller of the two ponds on the property, and the Atlantic Ocean beyond. Designed by Gary Graham of Boston-based GMI Architects and completed in 1985, the four-bedroom home is dominated by floor-to-ceiling windows that maximize the spectacular 180-degree views. Five wood-burning fireplaces ensure the island and New England vernacular so fundamental to the design is part of the interior too.

Homer’s Pond has been home to the current owners for the past 30 years. 

Designed for easy living, the house is divided into three distinct parts. The central structure is the ‘main house’ that can operate independently year-round. Downstairs, a sunken living room and dining room with floor-to-ceiling glass doors are separated by a fireplace that is open to both rooms. The kitchen is open-concept with an island and state- of-the-art amenities. Upstairs is a master suite with an office and a bedroom, his-and-her bathrooms with a chute to the basement laundry, and a private deck that offers unrivalled views of the island landscape and ocean.

To the west is the ‘pool house’ where the gym offers striking ocean views along with a sauna and steam room providing further relaxation and sanctuary. There is another bedroom here as well as a loft-like living room/ office with a wood-burning fireplace and more dramatic ocean views from the private terrace.

While expansive decks connect them, the three main structures were carefully sited to provide privacy. Extending out from the pool house is a semi-circular open garden wall framing the views across the pool and the dunes to the ocean beyond. GMI was recognized for its innovative design by the American Institute of Architects with an award for Excellence in Architecture.

In addition to the main home, a charming one- bedroom beach house perched on stilts amid trees is just a few steps from the private beach.

Homer’s Pond has two special features that set it apart from other luxury real estate offerings. First, there is more than 1,200 feet of private oceanfront that adjoins a wide expanse of “forever wild” beach under conservation. Second, the property contains two private ponds that are home to ducks, swans, freshwater fish and otters as well as visiting deer and migratory birds. For tennis fanatics, there’s also a world-class Har-Tru court.

“It’s a wonderful place to live,” says the owner, who asked not to be named. “I’ve been fortunate to have this land for entertaining friends and family during all seasons. People tend to associate Martha’s Vineyard with the summer, but I find the fall and spring to be the most serene, especially near the pond. The view in mid- To the east is the ‘guest house’ with a media room complete with a wet bar and surround sound system. An apartment upstairs has two ocean-facing bedrooms that open onto a screened porch. November is as spectacular as the view in mid-July. The holiday season is special here, too.” 

That special place is an enormous property, but there is welcome news for those who might not want the entire kingdom. Buyers can opt to purchase a 100-acre parcel of land on the western shore of Homer’s Pond for $31 million, a 164-acre parcel on the eastern shore for $43 million, or both for $74 million.

Multiple building sites with wonderful pond and ocean views – ideal for individual homes, or compounds for families and friends – have been identified on each. The main residence sits in a third 50-acre parcel that can be bought in conjunction with either of the other two.

So, who might be in the market for such a unique property? “It could be a local buyer with ties to the Vineyard or someone from New York or New England,” says Carlson. “Some of Hollywood calls the Vineyard its home, so in addition to Silicon Valley, southern California could be the source. Or it could be an international buyer looking to diversify their portfolio. It may even be a group of buyers, attracted to the flexibility the different parcels present. Whoever the buyer is, they are someone who values privacy and beautiful views.”

??Does he believe the property will fetch the $118 million asking price? “Stay tuned,” Carlson says.

I asked the owner whether leaving Homer’s Pond will be a sad parting of ways. “I’ve enjoyed the property for 30 years,” he says. “It’s time to give others the opportunity to enjoy this special place.” southlightproperty.com

Image Credits: Robert Gothard.