Sylvester Manor Educational Farm on Shelter Island.

Sylvester Manor Educational Farm on Shelter Island. Credit: Randee Daddona


Long Island’s North and South Fork are like two arms reaching around Shelter Island, says the town’s supervisor, Gary Gerth.

As one of the islands situated between the two forks, Gerth says Shelter Island draws its name from being “an island sheltered by islands.” With that comes a peaceful and tranquil setting and a boating and fishing haven, he says.

“People say as soon as you get on the ferry, your blood pressure drops, and it feels like vacation time,” says resident Penelope Moore of Saunders & Associates.

The 12-square-mile town, which includes Shelter Island and Shelter Island Heights, has a year-round population of roughly 2,500 residents, Gerth says. That number reaches around 12,000 during the summer months, he adds, as residents take advantage of the island’s offerings. Newsday reported in April that Shelter Island officials were considering changes to the town’s short-term rental law, which requires a town license and two-week buffer between stays, to help residents who depend on summer rental income.

Surrounded by Shelter Island Sound and Gardiners Bay, Shelter Island is home to beaches, inns, eateries and the 2,000-plus-acre Mashomack Preserve, which accounts for nearly one-third of the island’s land mass and offers tours, activities and trails.

Gerth says there is a proposal to add bike paths to both sides of Route 114, the island’s main thoroughfare. He says the Historical Society, which hosts various events, underwent a recent renovation, adding a 2,800-square-foot history center with space for exhibits, offices and interactive educational programs. Shelter Island also is home to the Sylvester Manor Educational Farm, whose historical windmill is currently being restored, and the Pearlman Music Program, which offers musical training to young string players and hosts free summer concerts. Hotels in the area, among others, include The Pridwin, The Chequit and Sunset Beach Hotel, which features a restaurant, bar and boutique.

“People seek some sort of quietude on Shelter Island, but at the same time there are activities,” Gerth says. He adds that the island is self-sufficient, with stores, a library, a medical center and other essentials. “You don’t have to leave the island if you don’t want to,” Gerth says. “But it’s also a great springboard to different areas.”

This Shelter Island ranch, for $699,000, includes two bedrooms and...

This Shelter Island ranch, for $699,000, includes two bedrooms and one bathroom. Credit: Douglas Elliman Real Estate

Ferry service offers easy access from Shelter Island to the vineyards of the North Fork and the Hamptons on the South Fork.

“You are in the middle of the best of both forks,” Moore says.

The island — which also includes Ram Island, Little Ram Island, and the incorporated village of Dering Harbor — offers a variety of housing styles, from ranches to waterfront Victorians, Moore says. Prices, she adds, can range from around $600,000 to as much as $10 million. Because of Shelter Island’s seclusion and population, Moore says, “everybody knows everybody, and that makes it special.”


There is one co-op on the market in Shelter Island Heights for $375,000. 

This Shelter Island ranch on the market for $749,000 in...

This Shelter Island ranch on the market for $749,000 in May 2019, includes three bedrooms and two bathrooms.  Credit: Brown Harris Stevens


Between April 1, 2018, and May 16, 2019, there were 14 home sales with a median sale price of $1,062,250, according to the Multiple Listing Service of Long Island. The low price for that period was $700,000 and the high was $4 million. During that time period a year earlier, there were 12 home sales with a median sale price of $1,305,000. The price range was $584,900 to $2.85 million.


Town Shelter Island

Area Shelter Island, 6.5 square miles; Shelter Island Heights, 5.4 square miles

ZIP code 11964, 11965

Population Shelter Island, 1,333; Heights, 1,048

This Shelter Island farmhouse, for $899,000, includes three bedrooms and...

This Shelter Island farmhouse, for $899,000, includes three bedrooms and 2-1/2 bathrooms. Credit: Daniel Gale Sotheby’s International Realty

Median age Shelter Island, 48.2; Heights, 58.0

Median household income Shelter Island, $110,148; Heights, $120,787

Median home value $999,500*

LIRR to NYC from Greenport, 2 hours 50 minutes at peak

Monthly ticket $500

School district Shelter Island

SOURCES: 2010 Census;; LIRR;

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


$727,000, Saint Mary’s Road

Style Farmhouse

Bedrooms 3

Bathrooms 2 full, 1 half

Built 1908

Lot size 0.71 acres

Taxes $4,721

Increased $77,100

Days on the market 106

$999,500, Sunshine Road

Style Farmhouse

Bedrooms 4

Bathrooms 3

Built 2013

Lot size 0.92 acres

Taxes $4,500

Reduced $195,500

Days on the market 83

$1.98 million, Tarkettle Road

Style Contemporary

Bedrooms 4

Bathrooms 5 full, 1 half

Built 2001

Lot size 1.1 acres

Taxes $11,605

Reduced $315,000

Days on the market 236



This ranch, on a 2.2-acre property, includes two bedrooms and one bathroom. It features a living room, formal dining room and eat-in kitchen. The property has two detached garages that total 1,221 square feet and can hold up to five cars. Taxes: $3,030. Christine Beckwith, Douglas Elliman Real Estate, 631-365-6091


This ranch, with three bedrooms and two bathrooms, has an open floor plan featuring a living room with a fireplace, kitchen and dining area, plus a family room and an en suite master bedroom. The half-acre property includes an attached 2 1/2-car garage. Taxes: $2,813. Barbara Brundige, Brown Harris Stevens, 516-242-7878


This farmhouse, with three bedrooms and 2 1/2 bathrooms, features a living room with a stone fireplace, an eat-in kitchen with stainless steel appliances, and a first-floor master suite. The house, on a 0.97-acre lot, also includes a screened porch, basement and attached two-car garage. Taxes: $4,703. Debra Von Brook Binder, Daniel Gale Sotheby’s International Realty, 631-872-2889

On Multiple Listings

Number of houses Shelter Island, 9; Heights 13

Price range Shelter Island, $699,000 to $1.595 million; Heights, $760,000 to $9.75 million

Tax range Shelter Island, $2,813 to $11,261; Heights, $2,600 to $22,376

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