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Photograph by Tyler Sands

The North Fork’s quaint bed and breakfasts, bucolic horse farms, vineyards, beaches and boat life make it an idyllic getaway. But who could blame a vacationer for wanting more than a slice of this haven? It’s primed for purchase too.

Paradise doesn’t come cheap here. Estates can cost between $800,000 and $6 million, more or less. They can come in many forms—waterfront homes, B&Bs, horse farms, and even artist’s retreats for creatives. The scarcity of these unique estates only enhances their exclusivity and preserves their value over time.

So you could say the investment potential here on the North Fork is sound, no pun intended. Depending on your lifestyle, finding the right property can be a challenge. However, local real estate agents are an enthusiastic resource.

If you’re in the market, we tapped some of North Fork’s top brokers and agents for expert tips that can help you land your dream home. You’ll discover some prime locations, scenic beauty, and a recreational wonderland on this journey. A little insider knowledge goes a long way in this competitive market.

“Buyers often prioritize spacious layouts and multiple bedrooms to accommodate family and friends comfortably,” said Jerry Cibulski, a broker for Century 21 Albertson Realty. “They also value properties with potential for rental income, allowing them to offset maintenance costs and potentially generate income when not in use.”

Whatever property you pursue, ensure that is in the right zone and location for its intended use. You can look up eCodes online, and lean on your agent or attorneys to avoid potential municipality pitfalls. Novel estates discussed here rarely come to market, so if you find one, jump on the research and act quickly.

With that in mind, here’s some agent/broker advice for purchasing some of the aforementioned estates unique to the North Fork.

So you want to buy a waterfront home:

Waterfront property is prime real estate. The North Fork’s coastline offers breathtaking views, private beach access and a luxurious waterfront lifestyle. Many of these shoreline homes feature architectural design elements like natural textures, white oak floors and millwork cabinetry that complement indoor-outdoor furniture.

But don’t let mesmerizing coastal views, sun-soaked waters and patio pools rush you into a poor decision. When considering a waterfront home, you must go through laborious checks on insurance costs associated with flood zones, wind, bulkheads and wetlands, especially if you plan to expand the home.

Photograph courtesy of The Agency

“When buying a home on the Long Island Sound, the health of the bluff and condition of any beach stairs should be reviewed by an engineer,” said Bridget Elkin of Compass. “And choose building materials that will stand up to wind and salt water. Properties in the water have higher maintenance costs versus off-water homes.”

That’s just the first step. Property seekers must also be aware of setback requirements and potential town Trustee/state Department of Environmental Conservation approval before permits are issued for building or renovating. That is if you can build at all. Melissa Principi of Douglas Elliman recently showed clients a small 600-square-foot waterfront cottage in Southold for $1 million, but the deal blew up because the home could only be expanded on its current footprint due to nearby wetlands.

“That meant my clients could only add a small 600-square-foot second floor,” she said. “They ended up not purchasing it because the idea of only a 1200-square-foot house and the cost of constriction was not worth the million-dollar buy-in for them.”

So you want to buy a bed and breakfast

A bed and breakfast is more than a residence, it’s an investment asset — and the ultimate remote job. Both help generate income and boost market value. That’s not counting the casual business lifestyle the owner enjoys, especially during summers when guests can ultimately become friends. But you’ll need to set up the infrastructure if you go the B&B route. 

That should include: a separate living space for a full-time owner or manager, en-suite guest bedrooms, a kitchen and large guest dining area, laundry facilities and multiple interior and exterior sitting vignettes to add visual appeal to the home, Sheri Winter Parker, a broker for Corcoran, told us. Think of what guests love and upgrade as many amenities as you can, such as private bathrooms, a pool or a sunset rooftop deck. Nice appliances and fixtures matter too.

You’d also be wise to scout the local area for nearby restaurants, entertainment and attractions which can give you a leg up over other B&Bs. That translates to more guests and profit. Many North Fork B&Bs are grand homes from the early 19th century that appeal to people who love hosting guests on the North Fork Wine Trail experience. 

“For this specific type of property, access to amenities outside of the home will be important for your guests,” Winter Parker said. “Some might be coming without transportation, so being near town or within walking distance to food and shopping will be a valuable asset.”

B&Bs can be created or come plug-and-play, so expect to pay anywhere from $800,000 to millions of dollars. And, of course, consider the quality of the home. Make sure everything is permitted according to the local town codes and that the septic is up to the bedroom count. B&Bs are highly regulated by towns and health departments, so buyers should consult with a zoning attorney first. 

“There’s always a trade-off between condition and price, but purchasing a home that is ‘turn-key’ eliminates unknown costs,” said Cheryl Schneider of The Agency Real Estate. “It’s also helpful to know if a property has any history or past use as a B&B to expedite the permitting process.”

So you want to buy an artist’s studio

The arts scene on the North Fork is a vibrant one. Its tranquil surroundings foster artistic expression. After all, something has to go on the walls of these impressive properties. With so many creatives and art lovers in the area, you may want to invest in a home that can be used as an artist’s retreat space or art studio.

These properties come to market maybe once a year, if that. When they do, review the certificate of occupancy because they’re not always legal in the eyes of the town, Principi said.

The two most important things with an artist’s studio are expansive walls and separating the workspace from the living space. And depending on the scope and scale of the art, you’ll want a large egress area with high ceilings.

“It’s hard to put a price on this kind of a property as they are pretty rare,” Winter Parker said. “You could build one. But, of course, make sure you’re working with a licensed contractor that knows the town code, as there has been a change to the height restriction and lot coverage in Southold,” she said.

Changes in work-life balance and transition from office commutes to work-from-home have shown creatives the value of these properties, Cibulski said. “It is important to check the zoning codes to be sure these workspaces align. And when they do, they are magical, visual and defintelty inspire creativity.”

So you want to buy a farmhouse

A rustic or modern farmhouse might be more your style. They can offer serene countryside charm, spacious plots of land and potential for vineyards, livestock or fruit farms. They generally run from $1.5 million to $3 million.

Original farmhouses may require a bit of TLC but if you take off all blinders and see the potential, you can make it your own. For instance, old farm homes don’t always include a typical primary bedroom with an en suite bath, but adding one is a nice perk.

“You want and should have an emotional response to the house you purchase,” Elkin said. “That said, older homes require a lot of love back, so it’s important to look past the furnishings and charm and have a practical outlook on the work required to maintain the property.”

You can always hire an architect, designer or builder to blend the integrity and character of traditional detail with modern elements that come with new construction. For example, since farmhouses are about warmth and charm, Elkin suggests adding a screened-in porch. But always keep future investment in mind. “Design the property that is right for you but keep resale in the conversation,” she said.

So you want to buy an equestrian property

The “gentleman’s farm” appeals to equestrian enthusiasts with maintained stables and riding facilities that could be used for recreational or business purposes.

“Living with your horse is a lifestyle choice, similar to a boater having a dock on their property to house their boat,” Winter Parker said. “It is very special to have the right amenities to make this a reality.”

While farms vary based Again, research the requirements for such a unique estate. Farms also vary based on development rights and the number of structures, buyers should be prepared to spend $1.5 to $4 million.

“For a gentleman’s farm, it’s all about the acreage,” said Principi. “Smaller gentleman farms under 30 acres with multiple structures like farmhouses and stables are rare and extremely coveted.” 

Winter Parker’s Mattituck listing shown here include 10.7 acres and features a main house, a 16-stall barn and a detached cottage.