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This recently renovated cottage located at 32660 Main Road is listed for $16,000 for the season. $5,000 for June and $7,000 each for July and August. (Credit: Town and Country Real Estate, courtesy)
This recently renovated cottage located at 32660 Main Road is listed for $20,000 for the season. $5,000 for June and $8,000 for August. (Credit: Town and Country Real Estate, courtesy)

Tired of spending your summers in Red Hook or Massapequa or wherever you call home? We recommend renting a quaint cottage or waterfront aerie, as whatever you fancy is sure to be found among the farms and vineyards and along the rugged coastline of Long Island’s charmingly anti-chic North Fork. Who knows? After spending a week, month or summer out here, you might just switch from being a renter to a buyer.


Credit: Town and Country Real Estate, courtesy
This home is listed for $30,000 for the season. (Credit: Town and Country Real Estate, courtesy)

If you sneeze, you might miss this tiny hamlet as you motor past the profusion of vineyards on both sides of Route 25. Peconic’s tiny geographic imprint is reflected in its small number of summer rentals — as of presstime, there were 11 ranging from $1,500 per week to $85,000 for the season.

Real estate agent Nicholas Planamento of Town & Country Real Estate holds two of those listings. The first is a midcentury A-Frame nestled in the dunes of Lacey Beach and situated steps from Peconic Bay, which he describes as “a cathedral of light.” The three-bedroom house at 1540 Robinson Lane boasts bay views and a massive stone fireplace and costs $3,000 per week or $25,000 for the season.

Planamento’s second listing is a three-bedroom Soundfront beach house built in 1939 with fabulous views and dramatic sunsets. Located at 380 Sound Ave., it’s $3,000 per week or $30,000 for the season.

For those with higher budgets, Indian Neck Farm is a sprawling creek-front estate owned by a billionaire. The 135-acre property features a 19-acre vineyard, deepwater dock, gunite pool, tennis court and 14 buildings, including a five-bedroom house. Alas, the owner’s stable of polo ponies is off-limits. Listed by Jeanmarie Bay of Town & Country Real Estate, it’s $85,000 for the season.


The Winemaker Studio — An intimate tasting room featuring the current releases of local vintners.

The Lenz Winery — Known for estate-bottled wines from mature vines.

Greenport Harbor Brewing Co. — Despite its name, this small-craft brewery has a second location in Peconic and features a brew pub.

North Found Co. — This shop’s eclectic array of home furnishings, objects, apparel and accessories express the vision of its owners — an interior designer and a clothing designer.

Breeze Hill Farm and Preserve – A splendid catering hall, this 72-acre property also boasts a bounteous farm market with food ranging from homegrown apples to scrumptious donuts.

Sannino Bella Vita Vineyard – Not only can you taste their wines, but you can also take winemaking lessons.

Shelter Island

Credit: Town and Country Real Estate, courtesy
Shelter Island’s Bumblebee Manor is listed for $100,000 for July or $125,000 for August. (Credit: Town and Country Real Estate, courtesy)

Since it can only be accessed by air or boat, Shelter Island is the East End’s most secluded area. Its coastline still boasts the imposing seaside mansions built when the island was a yachtsman’s resort, while its interior is dotted with modest antique farmhouses. Shelter Island Heights is a stronghold of colorful “carpenter gothic” abodes and another nostalgic throwback: a pharmacy that has been serving egg creams at its counter for a century.

“From bungalows to ranches, high-end modern and Spanish-style homes, there is a large variety to suit anyone,” says Douglas Elliman real estate agent Christine Beckwith. She recommends such appealing residential areas as Hay Beach and Silver Beach.

Beckwith has a nearly two-acre property atop a hill with views of ponds and meadows. “Reminiscent of a European country home,” the four-bedroom dwelling features walnut floors, cedar vaulted ceilings, oversize windows and a 24-foot double-sided fieldstone fireplace. Located at 33 Peconic Ave., it costs $28,000 for July, $35,000 for August through Labor Day, or $14,000 short-term.

There is also Bumblebee Manor, a Gatsbyesque compound on three-plus waterfront acres with a 16,00-square-foot main house. Besides the rolling lawns, infinity-edge pool and deep-water dock there is also tennis. Listed by Nicholas Planamento, it’s $100,000 for July and $125,000 for August through Labor Day.


Sunset Beach — A happening boite known for its French beachside dining and beautiful-people watching.

Sylvester Manor — This former 17th-century slave plantation is now a working farm and cultural destination, offering lively concerts and tours of its 1737 manor house.

Mashomack Preserve — One of the richest wildlife habitats in the Northeast, its woodlands, meadows and marshes cover a third of the island and offer unsurpassed hiking.

Notable Restaurants — Vine Street Café, 18 Bay Restaurant


(Credit: Town and Country Real Estate, courtesy)
This recently renovated cottage located at 32660 Main Road is listed for $20,000 for the season. $5,000 for June and $8,000 for August. (Credit: Town and Country Real Estate, courtesy)

About a mile east of Route 25’s causeway and past the scenic salt marshes, you will enter the historic district of Orient. The hamlet is so-named because it’s the tail end of the North Fork — in other words, it can feel about as far away as China. Many of the houses here were placed on the National Register of Historic Places some 40 years ago.

Orient’s main street, Village Lane, has some quaint retail spaces including Orient Linen Company and Old Orchard Farm Store — two stylish yet very different shops — and Four & Twenty Blackbirds, a satellite of a Brooklyn pie shop.

“There are only about 10 to 20 rentals every summer, and usually for only a month,” says Janet Markarian of Daniel Gale Sotheby’s International Realty. “People here don’t love giving up their homes.” She estimates prices as “anywhere from $5,000 for June to $100,000 for the season.”

One of her listings is a three-bedroom 19th-century farmhouse in the heart of the village with an updated country kitchen and bay views from the front porch. Located at 95 Navy St., it’s $28,000 for the season.

There is also this recently renovated 1920s two-bedroom cottage which sports a gourmet kitchen and a fenced-in yard with towering trees and gardens. But what’s best is its location abutting a working farm and distant views through meadows of Orient Harbor. Located at 32660 Main Road and listed by Lori Feilen of Town and Country, it costs $16,000 for season; $5,000 for June and $7,000 each for July and August.


Orient Inn — As you house hunt you can stay in the restored Arts and Crafts-style abode, which offers a central hall with fireplace and a great room for moments of repose.

The Candyman — The shop’s fourth-generation confectioners specialize in homemade chocolate.

Orient Beach State Park — Hiking trails meander along 45,000 feet of frontage on Gardiner’s Bay and through a rare maritime forest with red cedar and prickly-pear cactus. In this Audubon Important Bird Area, egrets, herons and osprey are commonly sighted.

The Orient Country Store — A café and general store serving delectable homemade soups, sandwiches and baked goods.

Oysterponds Historical Society — Maintains six historic sites and contains an archive of over 70,000 documents and artifacts.

This story originally appeared in the March 2017 issue of northforker magazine