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The Hamptons may be synonymous with beach living, but its beautiful villages are also booming. In Sag Harbor, a whaling town founded in 1707, buyers are trading the waterfront for the charm of historic American architecture — not to mention the convenience of a year-round town. Currently, three vintage beauties straight out of “Moby-Dick” are on the market along a stretch of Sag Harbor’s Main Street — known as Captain’s Row.

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This charming and meticulously restored 1840s captain's home, at 330 Main St. in Sag Harbor, is available for $3.3 million. The four-bedroom home boasts a library and six fireplaces.
This charming and meticulously restored 1840s captain's home, at 330 Main St. in Sag Harbor, is available for $3.3 million. The four-bedroom home boasts a library and six fireplaces. Douglas Elliman
This charming and meticulously restored 1840s captain's home, at 330 Main St. in Sag Harbor, is available for $3.3 million. The four-bedroom home boasts a library and six fireplaces.
Douglas Elliman
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This charming and meticulously restored 1840s captain's home, at 330 Main St. in Sag Harbor, is available for $3.3 million. The four-bedroom home boasts a library and six fireplaces.
Douglas Elliman
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“During the winter, the Hamptons can get very lonely,” says David Cox of Corcoran, who marketed 245 Main St., an 1870s whaler’s cottage with custom millwork, leaded-glass windows and hand-pegged wood beams, for $5.9 million (it’s currently in contract). The 5,100-square-foot, five-bedroom house has been given a respectful update that includes a swimming pool and clever smart-home technology. “But part of the charm of Sag Harbor is waking up when there is snow on the ground and walking into the village.”

Nearer to the bay, 330 Main St. is a carefully renovated 1840s captain’s home, with a classic wood-shingle facade and a $3.3 million price tag. It has four bedrooms and three bathrooms, plus a library, six fireplaces, landscaping and impressive water views from practically every room.

A bit farther down Captain’s Row — across from the Sag Harbor Whaling and Historical Museum — 207 Main St. is asking $3.9 million. The Federal-design, three-bedroom, two-bathroom masterpiece was built in 1789. Its recent renovation blends modern amenities (like central air) with 18th-century charm (shutters and original hardwood floors).

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Also on Sag Harbor's historic Captain's Row, this 1870s whaler's cottage at 245 Main St. was recently on the market for $5.9 million. It features historic details like custom millwork and leaded-glass windows, while modern updates include a low-slung pool and smart-home tech.
Also on Sag Harbor's historic Captain's Row, this 1870s whaler's cottage at 245 Main St. was recently on the market for $5.9 million. It features historic details like custom millwork and leaded-glass windows, while modern updates include a low-slung pool and smart-home tech. The Corcoran Group
Also on Sag Harbor's historic Captain's Row, this 1870s whaler's cottage at 245 Main St. was recently on the market for $5.9 million. It features historic details like custom millwork and leaded-glass windows, while modern updates include a low-slung pool and smart-home tech.
The Corcoran Group
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Also on Sag Harbor's historic Captain's Row, this 1870s whaler's cottage at 245 Main St. was recently on the market for $5.9 million. It features historic details like custom millwork and leaded-glass windows, while modern updates include a low-slung pool and smart-home tech.
The Corcoran Group
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