Best Metro NY Listings: Bridgewater, Setauket, Woodstock

Part of living in New York City is thinking about moving out of New York City. Each month, we’ll round up the best listings within commuting-ish distance, places where entire houses go for the cost of a “junior one-bedroom” (or less), but you’ll have to fix your own toilet.
This month, we’re doubling down on bonus buildings, including an $899,000 cottage with a private boathouse on Port Jefferson Harbor in Setauket and a clapboard home with an artist’s studio for just under $800,000.
$725,000; three-bedroom, two-bathroom
Photo: Sotheby’s International Realty
This 1840s home is a lot to take in, what with the myriad, ornately framed oil paintings and historical maps lining the hallway and lounge areas, faux-fruit displays, and rooms brimming with portraits and antique cabinetry. Still, it’s got some zippy charm, particularly in the kitchen, where delft-blue tiles line the backsplash above the electric-blue Kucht oven and burners, plus the starred maroon and faded floral wallpapers lining the bedrooms upstairs. Per the listing, the property comes with a separate artist’s studio that was once a blacksmith’s shop. If, like the seller, you have a lot of art yourself (or tchotchkes you can’t seem to part with), there’s clearly plenty of space for that, too. A five-bedroom, three-bathroom house nearby with a slightly smaller square footage went for $60,000 more last year.
How do I get back to the city?
It’s a roughly one-and-half-hour drive.
So what do I do if I live there?
Get a cold brew at the Bridgewater Village Store & Bistro before checking out the latest Louise Penny cozy at the Burnham Library.
$899,000; two-bedroom, one-bathroom
The cottage sits atop a bluff overlooking Port Jefferson Harbor, as seen in this listing photo, where you can go kayaking or sailing.
Photo: Douglas Elliman
Do you listen to a lot of Jimmy Buffett? What about any sailing aspirations? This two-bedroom home sits atop a bluff with sweeping views of Port Jefferson Harbor and Belle Terre across the way. A private staircase leads to your own slice of the shoreline (while it lasts), plus a salt-worn boathouse that has running water and electricity (“a rare find,” per the listing). The 1,000-square-foot home, which comes with a wood-burning fireplace and eat-in kitchen, is on the pricier side of recent sales along the block, but some updates have been made to the bathroom along with a new roof, bamboo flooring, and stainless-steel appliances. (Those questionable cherry motifs can easily be covered up with a quick paint job.)
How do I get back to the city?
It’s just under a two-hour drive.
So what do I do if I live there?
Learn to sail and make friends at the village dock just down the road or at the Checkmate Inn bar.
$799,000; three-bedroom, two bathroom
This Woodstock clapboard home’s windows provide a clear view of the adjacent 60-acre Thorn Preserve, as shown in this listing photo.
Photo: Coldwell Banker Village Green
Another twofer: The main dwelling is an 1875 clapboard home that sits on 1.89 acres of land, with windows looking out onto the well-forested Thorne Preserve, plus two bedrooms and a spacious kitchen-dining area; across the driveway sits a slate-gray accessory dwelling centered on a Morsø wood stove that has an eat-in kitchen and a bedroom and currently does double duty as a studio and guest house. The listing is pushing, somewhat aggressively, for in-ground pool installation and converting the smaller structure into a pool house, but, hey, follow your heart’s upstate calling. A fully fledged three-bedroom home on nearly five acres that borders Thorne Preserve sold for just under a million dollars in November.
How do I get back to the city?
It’s a little over a two-hour drive.
So what do I do if I live there?
See bands perform at the Colony and work on your swing at the Woodstock Tennis Club.
$748,000; four-bedroom, three-bathroom
This home was constructed in 1795 as a one-room dwelling but was expanded and today melds original and modern details, as this listing photo shows.
Photo: Coldwell Banker Village Green
The Besimer House was constructed in 1795 as a one-room stone dwelling but was expanded in the 1850s and today melds original details with modern appointments. Exposed hand-hewn beams hang above a bluestone fireplace in a living area, while a precious reading nook upstairs incorporates the 18th-century stone wall. But there’s an updated en suite bathroom in the primary room, plus premium appliances including a Miele dishwasher and a Kohler farmhouse sink in the kitchen, which could explain the nearly $125,000 price gap with a 2,700-square-foot three-bedroom that sold in August 2024. Still, it’s currently on the market for a hair cheaper than it sold for in 2022 and could be yours for the price of a Bed-Stuy one-bed.
How do I get back to the city?
It’s a two-hour drive.
So what do I do if I live there?
Bike along the Hurley Rail Trail, which is within walking distance of the property, then chew on ribs at Hickory BBQ.
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