Splurge vs. Steal: Two Gorgeous Cape Cod Houses in Chatham, Massachusetts

All of Cape Cod is beautiful, but the seaside town of Chatham, Massachusetts, is particularly charmed. With storybook houses and the landmark 19th-century Chatham Lighthouse, it’s a destination for many vacationers looking for peaceful relaxation and gorgeous surroundings.

Located on the southeastern tip of Cape Cod, Chatham was first settled in 1664 by the English. Its population of 6,125 swells in the summer months with tourists, many of whom have bought a home in this picturesque, tony town. It’s rumored Harry Connick, Jr., has been one of them.

We’ve found two homes in Chatham, one a splurge and one a steal. See how you can get a taste of Cape Cod living with these beauties.

Splurge vs. Steal: Two Gorgeous Cape Cod Houses in Chatham, Massachusetts

Downtown Chatham

 

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It’s no surprise that Hawaii captures the imagination of people dreaming of a getaway. Tropical breezes, the deep blue Pacific, technicolor sunsets, and lush greenery set the stage for a dream vacation or the ultimate home away from home.

Leading Real Estate Companies of the World and Luxury Portfolio International have announced the winners of the HGTV Ultimate House Hunt, a month-long online contest held on HGTV.com each year.

The contest highlights exceptional homes from across the globe in eight exciting categories: Waterfront Homes, Master Retreats, International Homes, Living Large in Small Spaces, Bringing The Outside In, Kids’ Spaces, Classic Living and Making an Entrance. All featured homes are represented by members of Leading Real Estate Companies of the World and Luxury Portfolio International. Consumers vote for their favorite, and a winner is chosen at the end.

This year, Hawaii cleaned up, winning honors in three categories as well as the overall winner. Massachusetts homes won in two categories, as did Florida homes and the International award winner is located in Lugano, Switzerland.

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In Provincetown, Cape Cod.

Every June, my family and I rent a cottage in Orleans, Mass., for a week, which is in the heart of Cape Cod. Our place is right on the bay, and we watch the tide ebb and flow from our large front porch. We just returned last week and the temperature was never above 80°. Last summer, it was so chilly, we rarely swam. The air smells clean and briny, and the architecture everywhere is like a storybook. If this sounds like paradise, you’re not far off.

cape codLife is pretty sweet in Cape Cod—I’ve had the opportunity to spend many hours driving and exploring the 15 towns that make up its 339 square miles. Cape Cod stretches from Woods Hole in the southwest (where you catch ferries to Martha’s Vineyard) to Provincetown in the northeast (where we go whale watching and fishing).

The year-round population of 220,000 swells during summer months, when many thousands like us flock to Cape Cod for a holiday. I can’t help but wonder what it would cost us to buy a place up there—it’s easy to afford something if your budget is massive, but what about more reasonably priced Cape Cod real estate?

I found three places that I think just might fit the bill.

 

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All photos: Leah Shafer

Cedar shake shingles for siding is a classic look for cottages all over Cape Cod. They are left unpainted and turn from light tan to a weathered gray over time. Clapboard siding is also commonly seen on Cape Cod cottages. All photos: Leah Shafer

Cape Cod has historic roots in American history, one of the earliest places the Pilgrims settled, later becoming a thriving fishing, whaling, and trading area.

But the romantic mythos of the Cape took off during John F. Kennedy’s presidential campaign, much of which was based out of the Kennedy Compound in Hyannis Port. JFK gave his acceptance speech there after winning the 1960 election, and returned frequently during his presidency. The Kennedy’s Camelot and Cape Cod are inextricably linked in the American imagination.

Today, the year-round population of 220,000 swells during summer months, when many thousands flock to Cape Cod for relaxation and resorts. It stretches from Provincetown in the northeast to Woods Hole in the southwest, and each of the 15 towns has its own individual character and hallmarks.

The sunset at low tide from our vacation house near Oster in Cape Cod.

The sunset at low tide from our vacation house near Orleans in Cape Cod. Stunning.

Cape Cod still maintains a charming, maritime feel, with almost 560 miles of wide, sandy coastline (including the gorgeous Cape Cod National Seashore), and house after house with weathered cedar shake shingle siding and colorful flowers that thrive in the temperate summer climate.

I just returned from a week’s vacation in Cape Cod, where we stayed in a classic shingle-style Cape beach house near Orleans on the inner bay. My fiancé’s family has vacationed there since the 1970s, and I joined them last year for the first time. As someone who spent her childhood summers in Galveston, Cape Cod was an enchanting experience, from windy afternoons walking by the seagrass along the shoreline to driving along winding roads with lush vegetation. The whole week we were there, the temperature never rose above 71 degrees.

Candy just wrote about the Cape for Grand Vie Magazine (read it here), and we both are delighted with the region and intrigued by the real estate market there. As Realtor Paul Grover of Robert Paul Properties in Osterville told her, 68 percent of his buyers were from Boston and its suburbs in 2013, and lots are empty-nesters.

But contrary to popular belief, Cape Cod is not just a haven for the rich and famous. As I discovered, there’s a range of housing available, with many beauties available for under $400,000 (I photographed 14 houses I’d consider classic Cape Cod cottage style that you can see throughout this post).

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It’s time to start thinking of your trip to the beach! A prime ocean view is a bit of an obligation. Given the price of oceanview property, which of course, they aren’t making any more of, the onus is on the builder and architect to craft a home that is both livable and delivers on the promise of a jaw-dropping vista.

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Jerusalem Road in Cohasset on Massachusetts’ South Shore has many homes that capture the classic look of a New England estate. Cohasset is a charming seaside town that offers many of the benefits of nearby Cape Cod but without as much of the tourist traffic (and no long wait to cross the bridge). This home, freshly built this year by Patrick Ahearn Architect and Fabrizio Construction, is a custom collaboration on a shingle style masterpiece with ocean views from 15 of 19 rooms!

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