Vacation Rentals By Owner In Shelter Island, NY

Traditional Hamptons style Home on a blissfully quiet cul-de-sac, with beautiful details, all impeccably renovated. Wrap around porch with three seating areas overlooks the expansive front yard. Roomy bedrooms, jetted tubs with separate showers in each full bathroom. The Primary Bedroom Suite has a Balcony that overlooks the large in-ground Saltwater Pool, generous Deck, Lounging and Dining Furniture, the large Propane Grill, and 6+ acres of natural preserved land. Formal Living Room with Baby Grand Piano; bright private Office/Library with large window seat; breezy screened in Sun Room; large well-equipped Chef’s Stainless Kitchen with marble counter tops, and a Dining Table that seats 8 comfortably. Basement/Game room with 10 foot ceilings, separate entrance leading to the Back Yard and Pool, two reclining couches, full wet bar, Pool Table with Ping Pong topper. Adjoining spa-like Bathroom with double sinks, jetted tub for two, WC, and a very generously sized walk-in Shower. There are 4 Large TVs with Cable and Premium Services in the Home. Shelter Island is a paradise all its own. Sunset Beach is 2 minutes down the road, and all other spectacular Shelter Beaches are under 5 minutes away. The Island has 2 Golf Courses, Hiking/Biking trails, Tennis, Restaurants, Bars, Boutique Shopping, and IGA, and million dollar views. Drive-on Ferry access is simple from the North or South Fork of Long Island. In just a few minutes you’re in Paradise!

Beautiful Spacious Traditional Home w/Pool, 2 minutes from Beaches, Golf, Tennis

Shelter Island, New York, United States

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8

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Beautifully appointed and recently renovated, spacious 3BR house + office, 2.5 bathrooms in Shelter Island (Hay Beach area, quiet street). The office can be fully closed and used as a guest bedroom. The house is quiet, private, and spacious (approx. 2700 sqf of built area + large patio/ pool and over 1 acre of land). Amenities include: Gunite pool with saltwater (6 chaise lounges in the pool area), large garden (small soccer field), outdoor, dining and patio lounge area (BBQ grill), ping pong table, and foosball table. The house is WIFI-enabled and has a SONOS sound system. Walking distance to two beautiful bay beaches. 2 adult bikes and 2 kids bike available for use. brNo smoking, no pets. brMonthly rates:brJune: US$17,000 brJuly: US$27,000brAugust: US$34,000 brAugust through Labor Day: US$36,000br2-week rentals available upon request. brUtilities included (ex pool heater).br

Recently Renovated Mid-Century Modern House in Shelter Island

Shelter Island, New York, United States

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8

Sleeps

$1770.88

Shelter Island is waiting for you at this 5-bedroom house. The bedrooms offer a nice mix of sleeping arrangements, including a king bed, queen beds, a twin bed, a bunk bed, and a sofa bed. The bathrooms are equipped with hair dryers and showers for your convenience. Enjoy the soothing atmosphere of this property, complete with amenities like a washing machine, AC, heating, WiFi, and more. We look forward to hosting you at our place. The property has its own dock and looks out over Wes neck Harbor and Shell Beach. Paddleboard, right off the backyard or sit on one of the many porches and relaxing, rocking chair, staring at the water and boats passing by. Watch the moonrise from one deck and the sunset from another with water views in 270°. A three minute walk from Salt, a great island restaurant and outdoor bar, destination or grill in the backyard and relax in the lounge chairs.

5-bedroom home on water with dock, office, bunk room in lovely Shelter Island!

Shelter Island, New York, United States

5

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Bath

9

Sleeps

$522.0

Nestled across a nature preserve, this lovely newly updated cottage is a perfect quiet spot to recharge your mind body and soul. Experience quintessential Shelter Island living. A 4-5 min walk to the best SI beaches and water access.

Silver Beach Hideaway: newly updated quiet cozy cottage - 4 min walk to beaches!

Shelter Island, New York, United States

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$1189.12

If you’re looking to escape bustling city life, book this 5-bedroom, 6.5-bath home in the Hamptons area! This Shelter Island vacation rental features an office and free WiFi, as well as amenities like a game room and pool to ensure a productive and restorative stay. With fun activities year-round, you can kayak on the nearby ocean, sip on some wine at the Wölffer Estate Vineyard, witness stunning views from Montauk Point, catch a Polo match, or get your holiday shopping done in the Hamptons!brbr-- THE PROPERTY --brbrSeasonal Outdoor Pool | Fully Equipped Home Gym | Free WiFi (High Speed) | 110 Mi to NYC | 5,000 Sq FtbrbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: 2 Twin Bunk Beds | Bedroom 5: Queen Bed | Bonus Room: King Bed brbrOUTDOOR LIVING: Private beach w/ wood-burning fire pit & beach chairs, kayaks (available spring/summer months), near ocean, walk to beaches, deck, gas grill + outdoor kitchen area, outdoor fireplace, fire pit, bicycles, boating, beach chairs, beach umbrella, trampolinebrINDOOR LIVING: 3 Smart TVs w/ cable, en-suite bathrooms, walk-in closet, laptop-friendly workspace, game room w/ pool table, gas fireplaces, dining areas, jetted bathtub, shower, booksbrKITCHEN: Refrigerator, stove/oven, blender, toaster, cooking basicsbrGENERAL: Central A/C + heating, complimentary toiletries, linens/towels, washers/dryers, hair dryer, hangers, beach towels, trash bags/paper towelsbrFAQ: Steps required for entry, bedroom + bathroom on 1st floor, zero-entrance shower brPARKING: Driveway (7 vehicles)brbr-- THE LOCATION --brbrTHINGS TO SEE + DO: Sylvester Manor Educational Farm - farm stand + theatre + live music in summer months (4 miles), Shelter Island Historical Society (5 miles), Horton Point Lighthouse Nautical Museum (12 miles), The Hamptons (16 miles), Parrish Art Museum (18 miles), Long Island Aquarium (29 miles), Montauk Point Lighthouse Museum (37 miles)brGET OUTSIDE: Lower Beach (1 mile), Upper Beach (3 miles), Coecles Harbor Marina & Boatyard (4 miles), Mashomack Preserve Entrance - walking trails (5 miles), 67 Steps Beach (8 miles), Sagg Main Beach - surfing, deep sea fishing, water sports (17 miles)brWINE & DINE: Ram's Head Inn (0.9 miles), Marie Eiffel Market (5 miles), Vine Street Cafe (5 miles), Greenport Harbor Brewing Company (7 miles), Kontokosta Winery (8 miles), One Woman Winery Greenport (10 miles), The Old Field Vineyards (10 miles), Sparkling Pointe Vineyards & Winery (12 miles), Channing Daughters Winery (13 miles), Wölffer Estate Vineyard (14 miles)brAIRPORTS: Long Island MacArthur Airport (58 miles), Laguardia Airport (101 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There are a few steps required for entry, but there is a bedroom and bathroom with a zero-entrance shower on the main floorbr- NOTE: The outdoor pool is open seasonally from May-September and the kayaks are only available in the spring and summer months

Shelter Island Retreat w/ Outdoor Pool!

Shelter Island, New York, United States

6

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7

Bath

10

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$333.33

Adorable studio with private entrance located on a quiet road. Kitchenette and large open living area with great natural light. Access to inlet perfect for kayaking, paddle boarding or watching sunset. Centrally located so easy to get to all that Shelter Island offers.

Apartment

Charming Studio on Shelter Island

Shelter Island, New York, United States

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Cottage

Silver Beach, 3 Bedroom cottage w/ pool

Shelter Island, New York, United States

Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped MCM ranch house on 3/4 of an acre. Located at the end of a private road, it's in walking distance to Shell Beach, town landings and a beautiful sunset viewing spot. Brand new, heated, inground pool w/ color changing light, central air, deck, fire pit and BBQ make this a great vacation home.

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2

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7

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This bright, cheery 3 bedroom / 3 bathroom Shelter Island cottage located in Montclair Colony is the perfect peaceful escape. Situated on a quiet corner with a new (2020), salt water, gunite, heated pool with automatic cover and large fenced in yard with outdoor shower.brbrThe mid-century beach bungalow was built in 1951 and offers great natural light and a beautiful cross breeze in every room.brbrThe main house is stylishly decorated and features an open layout with kitchen, dining room, living room, sun room, 2 bedrooms and 2 bathrooms. Central A/C throughout house (with exception of sunroom.)brbrCorner master bedroom has king size bed, ceiling fan, desk and large walk-in closet plus newly renovated (2021) en-suite bathroom with large shower and radiant heated floors. Second bedroom has full bed with convertible queen size day bed, ceiling fan and closet. Guest bathroom also newly renovated and includes shower/tub. brbrThe private guest house located above the 2-car garage has a separate entrance, queen size bed, kitchenette, 2 closets and window AC unit. brbrEntertain outdoors on the private deck with large table, ceiling fan, Adirondack rocking chairs & ottomans, chaise lounges and BBQ. Enjoy the expansive yard with outdoor shower, fire pit and fenced in vegetable garden. Includes beach chairs, beach umbrella, kayaks, ping pong table, cable, wifi and Sonos stereo system.brbrClose to the beaches, boat launch, restaurants and ferries. Walking distance to 3x town boat launches + Salt and Shipwreck.

50's Shelter Island Home w new pool, 3 bed 3 bath

Shelter Island, New York, United States

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Bath

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$2333.97

Stretch out and relax in this well-designed home high on a hill with truly spectacular water views from every room. Enjoy watching yachts and sea planes pull up to Sunset Beach, or peek over the Long Island Sound to Connecticut from the highest deck on the island. Or lounge by the pool and enjoy the one-of-a-kind sunset view, flowering gardens, outdoor kitchen and sunken dining area, large daybed and sectional sofa. Dog friendly!

Relax and Enjoy!

Shelter Island, New York, United States

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$1311.83

This home is a water lover’s paradise on sheltered water with easy access to surrounding east end towns. “2 East” features over 1500 square feet of decks & porch on three levels overlooking West Neck Harbor, with an opportunity to be in sun or shade and still enjoy spectacular water views. There are two deep water slips at our private dock for boats and ample room for swimming.brThe house is available summer season Memorial Day- Labor Day, or monthly July - Labor Day. Please contact owner for seasonal or monthly rates.brbr“2 East” has an open floor plan allowing guests to enjoy the outdoor view from within. The gourmet kitchen includes a Viking stove and two prep areas. Enjoy the water views from the dining room, or on the deck at the teak table under the market umbrella. The first floor includes a sun room, small media room, and a guest bedroom and bath. Upstairs there are two master suites with generous size bedrooms and baths. brbrSuite one has a king bed, spacious classic bath, and a sun deck overlooking the water accessible by French doors. It is perfect for waterside breakfast, afternoon cocktails, or just leisurely reading. In summer, the Big Dipper is directly over head for nighttime stargazing. brbrSuite two has a large bedroom with king size bed and an adjoining office (or child's room with foldout couch). High speed Internet access with wonderful water views makes any office work a pleasure. This suite also has a Jacuzzi bath and a large shower. High ceilings and ceiling fans give each suite a “country feel”, and the central a/c is rarely needed. brbrA deck surrounds the house in addition to the front porch. One portion of the property has a sandy beach perfect for swimming and kayaking that is adjacent to the bulk heading and dock. There is an outdoor food prep area, an outdoor grille and of course an outdoor shower. This house is the perfect setting for the ultimate summer living experience. brbrShelter Island has many fine restaurants and free concerts at the world renowned Perlman Music Center which is a few blocks away. There are many beaches and so many summer activities happening on the island. You will be able to have the beauty and serenity of the island and the house, and the stimulation of everything going on outside if you choose to participate. It is just a three minute ferry ride to Sag Harbor and the South Fork and all if its offerings and a ten minute ferry ride to Greenport and the North Fork with its farms and vineyards. brCome to “2 East” and relax, unwind and be surrounded by nature with its osprey, deer, red tail hawks and blue herons right out the window. br

Waterfront Charmer with boat slip on idyllic Shelter Island for summer rental

Shelter Island, New York, United States

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$378.54

Summer 2023 calendar has been updated ! The month of July is now available and can be rented for the entire period or in 2 week blocks- August 1-18 is also available Please note 2 week minimum rental period brbrThis serene, modern sun drenched spacious home is located on one of Shelter Island's scenic bays with full water access at the edge of the property. There is a dock which can accommodate small motor craft. There are also two kayaks- a single and a double -along with a canoe and 2 SUP‘s -all for renter use complete with paddles and lifejacketsbrbrThe spacious deck offers offers dining for up to 10 along with a large Weber grill area There is a separate seating area for loungingbrbrThis home was recently completely renovated by award winning Studio DuBois Architecture. The waterfront ground floor offers a high ceilinged open floor plan with kitchen, living and dining areas brbrThere cooks kitchen is fully equipped- Warm textured modern finishes make for inviting and relaxing living spaces throughout . The large Rumford fireplace provides extra coziness in the winter months. The TV room, with its large sectional sofa is perfect for movies, sports and binge watching. brbrThere are 3 beautifully appointed and generous en-suite bedrooms-2 of which are upstairs with waterfront views. The upstairs suites both have king beds and the downstairs suite has a queen bed. All bedrooms have ample closets, black out window coverings and are fully carpeted. There is a superb property manager on call.brbrThe house is centrally located and just minutes to the town center, Heights district and several of the town's main beaches. Wades Beach is down the road. brPlease note br- no children under 6( babies allowed )br- no pets br- one month rental preferredbr- 2 week minimum rental period during the summer seasonbrbrYour Shelter Island waterfront getaway awaits !

Shelter Island Sun Filled Modern Waterfront Home with Dock

Shelter Island, New York, United States

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$828.81

A 3 minute walk to wide sandy beach (Hay Beach/Menhaden Lane), this pristine 4 bedroom, 4 bath cedar clad three-level modern offers the essence of living in a treetop. With an entire wall of sliding doors in the living room overlooking cherry trees and wrap around deck, bay breezes waft throughout gently. The kitchen is a chef's delight, with granite counters, maple cabinets, Viking stove, Monogram refrigerator, Miele dishwasher, and sliding doors to an outdoor BBQ. STRONG WIFI /ORBI system throughout house.brbrThe first floor has two bedrooms with exotic sea grass floor coverings and skylights with shades and shared full bath. The second floor has a TV room/library with two balconies with scenic views, a spacious master suite with spa like bath and full bath in hall. The lower level is above grade, featuring a media room which is also convertible to a full bedroom with adjacent full bath. The grounds are sequestered and lovely, with a far-eastern influence. brbrThe heated Gunite pool has mahogany decking, lush bamboo gardens, sound system controlled through remote to the home, established red maples and river stone paths. The golf course is immediately adjacent. With a popular rental history, this home has all the ingredients for a fabulous vacation or work retreat! brbrHouse is about 2.0 miles from Island's main supermarket/IGA and 1.5 miles from Island's popular ice cream store/kids' mini golf course, Whales Tale.brbrNOTE 1: Child protected stairs, kitchen access, pool access, and optional door knob protector for stair access to lower floor.brNOTE 2: Extra cost associated with any utilities expenses above and beyond covered amounts.

Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach

Shelter Island, New York, United States

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Bath

Sleeps

$677.34

You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on the second floor wrap around deck. The second floor great room makes entertaining fun and relaxing. The kitchen, fully equipped with plates, cookware, silverware, glasses, etc, is open to the dining area and living area. The sunny master bedroom, furnished with a queen luxury mattress, is on the second floor and also has access to the deck. brThe first floor has 3 bedrooms, two with twin beds and one with a double bed, and a large common area where family members and guests can play and relax. There is a full bath on each floor.brThe house interior was painted in 2020 and has newer linens, rugs, and other amenities (all from 2020). brThe property has a large lawn where children can play.brYou are 10 minutes to golf and miniature golf, and to the grocery store. The beach is a 6 minute walk, around the corner. brShelter Island has a wonderful nature preserve minutes from the house as well.brWIFI available and TV.br

Family friendly home near beach with wonderful deck!

Shelter Island, New York, United States

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Bath

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$1433.85

Score Big at our fabulous Hamptons Cottage where work meets play in style! Settle into this charming 1700’s cottage nestled on 7 private acres of lush greenery adorned with majestic trees-your very own oasis! There are steep steps up to the second floor. br* Excellent Wifi: Say goodbye to buffering and hello to productivity with top-notch Wifi, ensuring seamless work-from-home sessions! br*Poolside Paradise: Dive into relaxation mode with a heated saltwater gunite pool-the ultimate spot to soak up the sun and splash around. Plus, keep an eye out for our resident turtles and frogs in the pond! Propane usage will be charged after stay.br*Cozy pool house: Need extra space Our pool house offers an additional bedroom, kitchenette and a half bathroom-perfect for guests or a private retreat!br* Outdoor Delights: Rinse out in style with an invigorating outdoor shower, then unwind on the screened-in-porch-an ideal spot for sipping your morning coffee or enjoying evening cocktails.br*Modern Comforts: This cottage is equipped with all the bells and whistles, including a recently installed chef's kitchen, A/C, heating, and a Sonos sound system-ensuring your stay is as luxurious as it is comfortable.br*Beach Bonanza:brJust a ten minute stroll lies Wades Beach, beckoning you with its sandy shores and sparkling waters-paradise found!br With room to accommodate up to 10 guests, this dreamy cottage is your ticket to an unforgettable Hamptons getaway. So grab your bags, grab your laptop, and get ready to blend work with pleasure like never before! Ahhhh Shelter Island!!

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

Shelter Island, New York, United States

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Bath

Sleeps

$1045.94

Amazing Waterfront Views.brAwaken to bird songs and swans gliding across the water. Sip coffee on the deck while planning the days adventures. Paddle board or kayak across the creek and have a swim at Wade’s beach. Come back and shower in the glorious outdoor shower and grill dinner and dine on the deck. Just as you think the landscape and the light can’t possibly get any more beautiful the sun begins to set and the light becomes even more beautiful. You will remember this special place and you will be thankful for the memories.

Lower Price Spacious Waterfront Property on Shelter Island

Shelter Island, New York, United States

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$707.26

This mid-century modern home sits on over an acre of land overlooking a tranquil pond. Located in the Shorewood section of Shelter Island just steps from a private beach and a 10 minute walk to the popular Wades Beach and access to a private tennis court across the street makes this a great summer escape. The open planned living room, dining room and kitchen with vaulted windowed ceiling adds great light by day and stargazing by night. All three bedrooms have sliding glass doors accessing the back deck and backyard. brbrThe furnishings are a mix of mid-century and modern, with white Egyptian cotton bedding in all three bedrooms. The master bedroom has a king bed, on suite bath and lots of windows and light. The second bedroom has a queen bed and lounging chair and the third bedroom has a twin sleep sofa, writing desk and chair, both rooms share a bath with shower in main hallway. Central air and ceiling fans in every room, make your stay comfortable.

Mid-century on idyllic pasture like setting with pond

Shelter Island, New York, United States

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$841.64

Welcome to Casa di Famiglia! Close to nature and the water, this family compound will rejuvenate your spirit. This property consists of a 3 bedroom 2 bath farmhouse that sleeps 6 including a queen pull out couch in the office. Also on the property is a 3 bedroom 1 bath pool house that sleeps 6 and has a living area with a kitchenette. The pool house is open from June 1st to October 15th. There is a lovely, private heated pool and a beautiful private backyard for relaxing and playing games. Enjoy morning coffee on the side porch and in the evening sit by the outdoor fire on the patio. Included in the rental are bikes to enjoy cycling around this beautiful island and kayaks to launch only 1/4 mile down the road. This property borders town nature walking trails ideal for viewing the diverse wildlife in the area. A water front restaurant, bar and The Island Boatyard Marina are walking distance from the house. This island is a boating paradise with boating charters available at the marina. The beach is a 5 minute drive. Between listening to all the bird song, smelling the salt air and relaxing in this most serene space, your visit to Casa di Famiglia will be a memorable one!

Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12

Shelter Island, New York, United States

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$230.13

Country Ranch five minutes to Mashomack Preserve hiking trails, beaches and miniature golf. Features include a living room, kitchen, dining nook, master bedroom(Queen bed), bathroom and guest bedroom with 2 twin beds, and washer/dryer. Pretty corner lot with a nice deck with a grill and seating for 5.

Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.

Shelter Island, New York, United States

2

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1

Bath

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$1250.76

Discover the beauty of Shelter Island from this Award winning, Architect owned and designed, 4-bedroom estate. brbrWhether you're lounging by the fireplace in the cozy clearstory living room or enjoying the fresh air on the spacious iconic wrap around porch, this property is perfect for a relaxing carefree summer getaway. The First floor encompasses an open floor plan seamlessly connecting kitchen, dining, living room and cozy den spaces as well as a private master suite. Second floor has 3 additional bedrooms and bathroom with access to an exterior observation deck perfect for bird watching with an early morning coffee. Guests will also have access and use of the first floor to the accessory 2 car garage structure on the property. brbrThis Property is located within a prominent Hamptons style estate area of the Island and within walking distance to multiple beaches. Bicycles, kayaks and paddle boards can be rented on island if so desired. And don't forget to take a hike at the Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, it is not to be missed. brbrWe hope you'll enjoy your stay at our estate.brbrNearby Beaches:brShell Beach, Crescent Beach (Sunset Beach), Crab Creek Beach, Bootleggers Alley Beach.brbrNearby Grocery Stores:brIGA brbrNearby Restaurants and Bars:brDan Brock's Barbecue at Ellie's country store excellent sides and puddings in mason jars.brbrMarie Eiffel- in the Heights a wonderful great take-out food.brbrRam's Head Inn- always special even just for cocktails on the beautiful lawn in Adirondack chairs.brbrKyles- fantastic homemade jelly and cinnamon doughnuts croissants and cakes.brbrCommander Cody's- great fish store, and fabulous barbecue- pan fried chicken, and take out fish.brbrVine Street Cafe- excellent food, five stars.brbrMaria's kitchen- great take out Mexican- great homemade chips and guac.brbrShelter island slice for pizza.brbrChequit- in town.brbrSaltbrbrLeon 1909

AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND

Shelter Island, New York, United States

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