One of the historical buildings by the Village Green in...

One of the historical buildings by the Village Green in Cutchogue. Credit: Randee Daddona


Along the streets of Cutchogue are farmland, wineries — even a welcome sign calling the North Shore hamlet the sunniest place in New York State.

“That’s been the claim for as long as I can remember,” says Southold Town Supervisor Scott Russell, a longtime Cutchogue resident.

Stretching from the Long Island Sound to the Peconic Bay, Cutchogue is small and quaint, creating an overall aesthetic that attracts home buyers to the area, Russell says

Coming soon to the hamlet, Russell adds, will be a condominium complex. Construction is underway on Harvest Pointe, a 124-unit 55-and-over complex with prices starting at $685,000. Russell says there is potential for development that will serve the community.

“With something of that large scale in a tiny hamlet, it is difficult to anticipate what people will perceive as needs and what will be developed around that,” Russell says. “But there is vacant commercial property in and around that area that’s been dormant for years.”

Sheila Izzo of North Fork Real Estate says that Cutchogue has adjusted to fit the lifestyle of today’s home buyers, but still maintains aspects of the rural setting that has mostly faded from other areas.     

“You go from the north part of Cutchogue and it looks like rural America, with farms and rolling fields and barns, to Nassau Point, where it's mega mansions and little beach cottages,” Izzo says. “So it’s almost like a dichotomy of two worlds blended together.” 

House prices, she adds, range from around $500,000 to homes that command as much as $8 million. Much of the hamlet’s new construction, Russell says, is being done on waterfront properties along the Sound, Bay and creeks that run through the area. Cutchogue has a variety of housing styles, offering everything from modern homes to traditional New England cedar shake houses, says Sheri Winter Clary of The Corcoran Group.

The area boasts a variety of beaches, some of which are along the Sound and others off the southern enclave of Nassau Point. Cutchogue is home to the North Fork Country Club, a private club dating back to 1912 that includes an 18-hole golf course, and also Cedars Golf Club, which has a nine-hole golf course. The Village Green, next to the library, features historical structures, including a house from the 1600s, and hosts various events throughout the year. Cutchogue has plenty to offer, says Winter Clary, particularly on a sunny day.

“The way the sun hits Cutchogue, there is something very special about it,” Winter Clary says. “The energy there is very tangible.”


There are none on the market. 


Between March 1, 2018, and March 29, 2019, there were 70 home sales with a median sale price of $735,250, according to the Multiple Listing Service of Long Island. The low price for that period was $295,000 and the high was $6.75 million. During that time a year earlier, there were 52 home sales with a median sale price of $664,500. The price range was $363,000 to $5.3 million.


Town: Southold

Area: 8.1 square miles

ZIP code: 11935

Population: 3,349

Median age: 49.4

Median household income: $93,125

Median home value: $740,750*

LIRR to NYC: From Mattituck, one train at peak, 2 hours 28 minutes

Monthly ticket: $500

School district: Mattituck-Cutchogue

SOURCES: 2010 Census;; LIRR

*Based on sales in the past six months, according to MLSLI



Pinewood Road

Style: Ranch

Bedrooms: 3

Bathrooms: 2

Built: 1983

Lot size: 0.34 acres

Taxes: $6,922

Increased: $1,000

Days on the market: 143


Stillwater Avenue

Style: Colonial

Bedrooms: 4

Bathrooms: 3 full, 1 half

Built: 2004

Lot size: 0.49 acres

Taxes: $8,928

Reduced: $150,000

Days on the market: 191

$1.3 million

Skunk Lane

Style: Farmhouse

Bedrooms: 6

Bathrooms: 6 full, 1 half

Built: 2001

Lot size: 2.65 acres

Taxes: $14,115

Reduced: $99,000

Days on the market: 142



This Cutchogue farmhouse, for $699,000, includes four bedrooms and two...

This Cutchogue farmhouse, for $699,000, includes four bedrooms and two bathrooms.  Credit: Coldwell Banker M&D Good Life

This farmhouse, with four bedrooms and two bathrooms, includes a formal living room with a fireplace, a kitchen with a center island and a formal dining room. The house, on 1.26 acres, also has a finished walk-up attic, full basement and detached 2-1/2 car garage. Taxes: $8,127. Gina Galante, Coldwell banker M & D Good Life, 631-767-1237


This Cutchogue home, for $825,000, includes three bedrooms and 2-1/2...

This Cutchogue home, for $825,000, includes three bedrooms and 2-1/2 bathrooms. 

This newly-constructed home, with three bedrooms and 2-1/2 bathrooms, features an open floor plan that includes a den with a wood-burning fireplace, an eat-in kitchen and a formal dining room with access to a back deck. The .25-acre property includes a detached two-car garage. Taxes: N/A. Carol Szynaka and Mariah Mills, Daniel Gale Sotheby’s International Realty, 631-734-5439

$1.3 million

This Cutchogue Victorian, for $1.3 million, includes four bedrooms and...

This Cutchogue Victorian, for $1.3 million, includes four bedrooms and 2-1/2 bathrooms. Credit: North Fork Real Estate

This Victorian, on a 3.34-acre property, offers four bedrooms and 2-1/2 bathrooms. The house includes a living room, formal dining room, eat-in kitchen, master suite, full basement and detached two-car garage. Taxes: $14,832. Sheila Izzo, North Fore Real Estate, 631-384-5551

On Multiple Listings

Number of houses: 24

Price range: $425,000-$5.5 million

Tax range: $4,420-$73,856

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