Charm and History Combine with Sag Harbor Main Street Real Estate

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A pair of adjacent houses on Main Street's "Captain's Row" have recently been on the market. Michael Heller photo

When a listing on Sag Harbor’s Main Street comes their way, many real estate agents in Sag Harbor say they find themselves thrilled, ready to get to work selling a property that differs in some ways from others around Sag Harbor and from those in other South Fork villages and hamlets.

Some agents report houses on Main Street generally have more visibility during the selling process, simply because of their location, and in the case of “Captain’s Row,” those houses come with historical narratives that lend great prestige. Many Main Street homes have status as buildings of architectural significance within the village’s historic district, dubbed “contributing” structures, which sometimes influences a sale. And sales, especially when it comes to commercial real estate, are often swift.

“It’s fantastic. It’s very exciting to have that listing,” said Mala Sander, a licensed associate broker with The Corcoran Group who sells across the South Fork market. “To a certain extent, yes, it’s different being on Main Street for so many reasons. The charm and the history will appeal to some and some others may not care about it. To me, it’s fascinating, these old homes. The ones that have had their historical details preserved are so special. Who doesn’t want to be in that lineage of owners of these grand properties? It’s so romantic.”

Gioia DiPaolo, an associate broker with Sotheby’s in Sag Harbor, agreed that a Main Street listing is a compelling one.

“Agents love to have their signs where they will be seen by a lot of people so from that perspective, a Main Street listing is great,” she said. “A historically significant Main Street property with original decorative arts elements intact is an exciting prospect, especially if it is properly priced.”

That’s a key factor. Priced right, a Main Street property apparently doesn’t stay on the market long. Ms. Sander’s listing at 264 Main Street went to contract within 60 days of its listing date, and closed for $3,995,000 in August of 2017. Another one, 278 Main Street, was listed July 4 weekend in 2015 and was in contract by Labor Day – ultimately sold for $3,995,000 to the first person who had come calling about the house.

And if prices fluctuate elsewhere in the village, that’s not necessarily the case on Main Street.

“I think that they’ll tend to hold their own relative to other parts of the village,” Ms. Sander said.“There’s always that caché. When there’s a downturn, they’ll hold their own, and when the market’s coming back they’ll come up quicker.”

The lot sizes along Main Street, Ms. DiPaolo said, are another factor that impact sales there. “Many of the lots on Main Street are larger than those found on smaller side streets and the houses tend to be larger as well, and that certainly affects their desirability,” she said.

When it comes to the historic district, through which Main Street passes almost in its entirety, Scott Strough, an agent with Compass Real Estate, says this factor has yielded “an extremely vibrant and active marketplace” not just on Main Street but on nearby roads, such as Union Street, Glover Street, Palmer Terrace and Oakland Avenue.

“I am of the belief that the more historic and the more historic background to the house, it adds value and also adds demand,” he said.

Maureen Geary, a licensed broker with Brown Harris Stevens, also said the history factor is a draw for buyers.

“There is such a great demand to be in the village and purchasers love the historical element, so being in the historic district is a definite plus,” she said.

Mr. Strough dismissed what he called a “bad rumor” — that being labeled as a contributing structure is going to diminish the property’s value. It can have the opposite effect when protections are put into place to preserve the quality of life throughout entire neighborhoods. And that’s where the Sag Harbor Board of Historic Preservation and Architectural Review comes into the picture. Mr. Strough said the board is upholding the character of Main Street.

“Without the HPARB, you’re going to have an erosion over time of the very essence of the historic district and the village of Sag Harbor,” he said. “Oftentimes when projects throughout the village get completed in accordance with the recommendations of the HPARB, they are beautiful. A lot of people argue with them and aren’t comfortable with their decisions, but at the end of the day they’ve got probably the most important job within the Sag Harbor government when it comes to preserving our identity.”

HPARB chairman Anthony Brandt said while he and his colleagues pay close attention to the entire historic district, they keep a special watch over Main Street in particular.

“It is what you might call the ‘Sag Harbor showcase street’ and, yeah, we approach it with care,” Mr. Brandt said. “It’s the basis for the American Planning Association’s designation of Sag Harbor as having one of the 10 best main streets in the country. That’s important, and we want to preserve it.”

Commercial real estate on Main Street is a no-brainer because there is practically none of it to be had.

“There’s not a lot of supply, let’s put it that way,” said Hal Zwick, an agent with Town & Country who himself owned a building on Sag Harbor’s Main Street for 13 years before selling it in 2015. “Sag Harbor is very sought after and you’re not going to build any more commercial space. If someone can buy something, they should because the value is only going to go up.”

He said the village has its downtown sewer system to thank for its strong commercial real estate market. The infrastructure can support many more “wet” uses such as restaurants than other hamlets and villages without sewer systems can support. Restaurants and related businesses draw foot traffic, which in turn draws more business.

“There’s more people in Sag Harbor walking the streets than in most villages,” Mr. Zwick said. “You can go in January to Southampton or East Hampton and there are very few people walking the streets, but in Sag Harbor, there they are.”

So the streets are therefore pretty busy, which can sometimes be a turn-off to would-be buyers toward the residential end of Main Street.

“Two opposing buyer perceptions I’ve encountered over the years about Main Street property: One group says, ‘It’s a busy street,’” Ms. DiPaolo said. “The other group says: ‘Main Street is the most prestigious street in the village.’”


A Sampling of What’s Available on Main Street Right Now

Photo courtesy of Corcoran Real Estate.

168 Main Street

This four-bedroom, six-and-a-half bathroom, 4,600-square-foot Greek Revival is listed at $6.7 million with Mala Sander of The Corcoran Group. The property was once owned by William H. Cooper, the boat builder and father of artist Annie Cooper Boyd, and the current house dates back to 1813. The property also includes a heated pool and a pool house with fireplace.

Photo courtesy of Brown Harris Stevens.

209 Main Street

This three-bedroom, two-bathroom, 2,059-square-foot house on Captain’s Row has been dubbed a “secret sanctuary” by Brown Harris Stevens listing agent Clare J. Tenkarian. Built in 1750, its features include a bathroom with a “rain shower,” a wine cellar, a greenhouse, a gazebo, a heated pool and more. It is listed at $2,750,000.

Photo courtesy of Town & Country Real Estate.

69D Main Street

This second-floor business condo, listed at $1.7 million by Hal Zwick of Town & Country, measures about 1,700 square feet and has a kitchenette and elevator access. Its last owner was an accountant. “Anybody can go in and tailor the space to their business,” Mr. Zwick says. “With village approval, somebody can probably make it into a residence if they want, because the third floor is residential.”

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