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Ideal Spots to Buy a Vacation Home on the East Coast

We spoke with a ONE Sotheby’s agent about the best cities, towns, and islands to purchase stunning coastal vacation property.


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Buying a vacation home is a big undertaking—and if you’re looking to invest in property on the East Coast, be it a mountainside ski chalet, a sprawling New England farm, or a beach bungalow in the south, the hardest decision you’ll likely have to make? Location, location, location. Of course, every region of the coast has a unique draw, but within each, you’re guaranteed to find eclectic, charming neighborhoods that boast beautiful views, award-winning cuisine, and ample opportunity for exploring the great outdoors.

If there’s one thing that Jill Penman, Estate Agent with ONE Sotheby’s International Realty, thinks clients should consider before they choose where to purchase property, it’s the type of lifestyle they hope to maintain in their new vacation home. “The primary draws for purchasing a vacation property are what makes the lifestyle unique to the specific region,” she said. “Vicinity to the ocean and beaches, great restaurants, fish and farmers markets, boutiques, and wineries are all good examples of what makes people want to purchase a coastal vacation home.”

We know what you’re thinking: where to start? “Two ideal spots to purchase a vacation home on the East Coast are Coconut Grove, Florida and the Hamptons. Coconut Grove is a unique waterside neighborhood in Miami. It is lush, bohemian, tropical, and full of great energy. A popular spot for Miami families, Coconut Grove offers marinas for boating enthusiasts, great parks, and a plethora of restaurants and entertainment.”

But if you’re looking to stay in the north Atlantic, Penman points to the upscale, iconic string of seaside Hamlets in coastal New York. “Further North, whether you are traveling from NYC, Miami, or the West Coast, the Hamptons offer a wide array of top-notch dining venues, vineyards, outdoor activities, fresh farmers markets galore, and beautiful beaches to enjoy the perfect summer weather. Other East Coast towns like Newport, Rhode Island and Woodstock, Vermont are also beautiful parts of the country. The lifestyle that the Hamptons offers, however, brings a different flavor of real estate and entertainment.”

Related: Where to Buy a Vacation Home in Florida

Interested buyers should take note that the market—as expected—varies markedly by region, and Penman noted that it’s difficult to summarize the East Coast real estate market as a whole. Factors like population and weather patterns fluctuate often and impact property prices and availability.

“Florida, for example, has seen the largest inter-state migration of wealth recently due mostly to the current tax environment,” she said. “Miami’s weather and general liveliness make it a city that’s always in high demand, and it still presents incredible value when compared to other world-class cities. Unexpected low-profile regions with good real estate values include parts of Florida, New Hampshire, Maine, and Vermont, where there are beautiful estates and opportunities to renovate older homes on acres of pristine land. Bar Harbor, Maine [for example] is a little hidden gem hugging the coastline.”

If you’re in the market for a small waterfront property, Penman recommends looking into purchasing a seaside condo. “For more low-key coastal escapes, travel down the coast and you’ll find plenty of wonderful towns with great value when it comes to beachfront condos. Areas like Hilton Head and Myrtle Beach, South Carolina; Tybee Island, Georgia; Rehoboth Beach, Delaware; and Cape May, New Jersey are all great vacation spots.”


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