Just a few minutes from Wades Beach is this private park-like enclave with a charming 2+ bedroom, 1.5 bath shingled home and brand new heated gunite pool. This fully fenced property has been lovingly landscaped over many years with bordering trees, a fruit bearing peach tree, gorgeous specimen Japanese cherry tree and successive plantings that flower continuously throughout the seasons. An open floor plan features a living room with fireplace, dining area, open kitchen and office with additional sleeping area, all with lovely views of the gardens. Two outdoor showers, a big deck, open porch and inviting seating areas under the trees and nestled among the flowers make this an idyllic and artistic retreat. Rest, relax, restore and enjoy the lovely new pool, nearby beach, kayaking and the beautiful sunsets over West Neck Harbor. Rental Registration # 23-2-38.1 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67008228
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Shelter Island 4 bedroom cottage. Fabulous mid-century cottage, beautifully restored, offering 4 bedrooms and 2 full baths. Outdoor shower, Jacuzzi, ping pong, media room, piano, large deck, washer/dryer, 3 bikes, huge front and back lawns. Very quiet and secluded. Near Coecles Harbor, Mashomack Preserve/Farm and Hay Beach. For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i71182663
Adorable cottage with waterviews in secluded Montclair Colony on south end of the island. Three bedrooms, 2 full baths, glassed in porch and sunny kitchen, quiet area. A great summer rental. Rental Registration # 2023-L-0083 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i70644507
Two Bedroom, two bathroom "Seashell Cottage" in Montclair Colony with enclosed porch with trundle bed. Living room with sleeper sofa. Separate dining room off the kitchen. Minutes from town landings for boat access or to swim. Enjoy the summer breeze in your private backyard or sit on the front porch and enjoy the views. For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i71896730
A romantic and secluded summer getaway. Enjoy a front row seat to breathtaking and dramatic views of the Shelter Island Sound, Crescent (Sunset) Beach, Quinipet Sailing, North Ferry, Greenport, Southold and 4th of July fireworks. Conveniently just steps from Kissing Rock, Crescent Beach, The Pridwin Hotel (Spa and Restaurant), Sunset Beach (Restaurant and Nightlife), Shelter Island House (Restaurant and Lounge), and Perlman Music Camp. This tranquil summer cottage is nestled in the hillside landscape, surrounded by trees for cooling shade, and is accentuated by a full and wide front deck overlooking the bay for relaxation, sunbathing, and cocktails. Enjoy an outdoor shower and stretch out on the hammock to relax, enjoy the view, watch the sunrise, and savor the solitude. 3 bedrooms (Queen + Queen + Full). An idyllic summer rental where summer memories will be made. Rental Registration # 2024-L-0012 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i70793964
This charming farmhouse features 3 bedrooms, 3 full baths, open living, dining, and a kitchen with doors out to the large deck with a pool. Located in the Silver Beach area of Shelter Island, it is within close proximity of the most beautiful beaches Shelter Island has to offer. A fun summer rental for family and guests which includes the use of kayaks, paddle boards, bicycles, and pool floats for those fun-filled days. Rental Registration # 2023-V-0003 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67628782
Also Available: Oct 4K, Nov 4K, Dec 4K This bucolic property on quiet Shelter Island offers the most peaceful environment. The lovely home was curated over the years by an artist-filmmaker couple and is perfect for its subtle aesthetics. The one-story dwelling has a natural flow along with central air, and outside a new heated pool, gardens and sculptures totally ensconced with mature landscaping and specimen trees. Back inside, the living room and fully-equipped kitchen are light/bright/white and looks out onto a wrap around deck equipped with a grill for casual dining. Of the two bedrooms, the master has a king bed and renovated bathroom. The guest room has a new half-bath, and they both have a work desk with wifi. There is a generous third room, presently an artist's studio, which is quite pristine, wall to wall windows and stands ready for an extra bed if need be. Back outside: There is a new, very high-end outdoor shower thoughtfully fitted with very handsome privacy doors. Among the robust plantings surrounding the outer areas of the grounds, one of the owner/artists has sited a delightfully stunning and sparse sculpture in wrought iron that is very much one with the land. Wonderful beaches, restaurants, markets, shops and galleries, one never has to leave the Island. But a quick ferry to Sag Harbor or North Fork, this property offers convenience as well as privacy at the right price. Rental Registration # 20-LT-0011 EH RR #: 20-LT-0011 Rental Terms: Other / Short Term - Jan 1 - Apr 30: $14, 000 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66971805
Stay two weeks in this charming four bedroom, two bath home features a living room with fireplace, den, country kitchen and large screened rocking chair porch with water view. Wake up early to explore the creek at sunrise or gather the gang for a splendid sunset walk. A special Silver Beach location. For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67059060
RR# 19L-0061 This grand compound bordering parkland is spectacular. The main house spans 4700 sf holds 5 bedrooms, 5.5 bathrooms, an open and spacious living room with fireplace, formal dining room, and a gourmet kitchen and top of the line appliances. Some of the luxurious amenities included are the theater room, game room featuring a billiards table and a bar, a heated Gunite pool with spa, putting green, guest house, and 4-car garage. For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67096120
Brand new 5 Bedroom, 4.5 Bath Contemporary Shelter Island home on an inlet off of West Neck Creek on the Menantic Peninsula. Spacious and filled with light, this beautiful home enjoys an open floor plan with vaulted ceilings and lots of glass in the dining and living area which has a charming floor to ceiling stone fireplace. Also open to a stunning kitchen with all-new stainless appliances, granite counters, and a breakfast bar. A comfortable family room with a half bath is conveniently located next to the kitchen and all common rooms overlook the water and huge deck which has a heated gunite pool and shaded seating cabana. A quiet guest bedroom suite completes the main level. The second floor has a gorgeous master suite with a spa-like bath and a waterside balcony deck. Two additional bedrooms, a bath, and a cozy office provide guest sleeping areas and more private space for reading and internet use. The finished basement has an additional bedroom, bath, playroom, and gym. Waterfront is suitable for kayaks and small boats and the house is close to island beaches and the Island Boatyard Marina for boating and fishing enthusiasts. Rental Registration # 2021-L-48 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67997807
Charming renovated cottage on lovely treed and landscaped half acre not far from the Island Boatyard Marina and both Wades and Crescent Beaches. Surrounded with beautiful trees affording a private country ambience, this immaculate 2 bedroom home with tiled bath and shower, has a covered front porch, great room with living and dining area open to a galley kitchen with granite counter and stainless appliances, a laundry room and screened porch which serves as a seasonal outdoor living room, expanding the total square footage. A large deck with sunning and dining area is artfully arranged with lovely planters and beach grasses for additional privacy. The back yard has an outdoor shower, storage sheds and a graveled area with seating and fire pit for cozy gatherings under the stars. The house is well furnished with a serene and modern design and also enjoys a full basement and convenient parking area. Available monthly or in two week periods. Rental Registration # 2023-V-0030 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66975622
This open and bright 3 bedroom 2 Bath with heated pool is the perfect place to enjoy August. Close to beach, Central Air, Outdoor shower, Pet considered For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i71181738
This wonderful cottage on bucolic Shelter Island has been recently renovated and is now available for summer rental. With spacious kitchen with dining table, island seating and breakfast patio outdoors. Large bright living room that looks out to back deck and yard. There are 3 great sized bedrooms and master overlooks the lovely yard. Two full bathrooms on this level and an additional lower level bathroom in the partially finished basement. With an expansive deck and mature landscaping on just over half acre close to Coecles Harbor and easy access to all Shelter Island beaches, farmstands, shopping and restaurants this will be a summer you and your loved ones cherish! Please call with any questions or to set up an appointment to view this property! Rental Terms: August - Labor Day: $17, 000 July - Labor Day: $28, 000 July: $13, 000 Memorial Day - Labor Day: $33, 000 Other / Short Term - June and July: $20, 000 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67111954
Available short term, this 4 Bedroom waterfront house creates incredible freedom between the insides and outside living areas. The expansive covered porch overlooking the water is a tranquil place to relax and entertain. The pool area is a special haven after a day on the water. Living room and dining areas are enhanced by the water view and surround you in comfort. Master Bedroom and outside courtyard create an elegant sense of nature. Modern, bright, and open this home is ready to enhance your Shelter Island vacation. Rental Registration # 2023-L-0101 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66920138
This large 5 bedroom+ farm house features large common rooms and bedrooms on 3 floors for privacy. Updated baths and a French country kitchen will be the delight for summer entertaining on both the large porch with sunset views and the covered veranda overlooking the private pool and gardens. All rooms are large and feature a European country flair. A wonderful summer rental with room for all. Prices shown are for a 2 week rental period. Please contact for available dates. Rental Registration # 2023-L-0010 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67102320
This pristine, recently renovated five bedroom Cape Cod is ready for summer! Conveniently located within close proximity to beach, fine dining, recreation areas, and bordering a preserve. Two story home with chef's kitchen, high end appliances, quartz countertops, and spacious living room with 82" flat screen TV make for wonderful gathering areas. Large outdoor entertainment deck with grill, patio seating, and outdoor fire pit is just the ticket for hanging outside and a summer barbecue. Beach gear and guest bikes are included for trips to all of Shelter Island nearby beaches. Rental Registration # 2023-V-0008 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i70233460
Beautiful water views from this charming renovated 3 bedroom, 2 bath shingled Cape on lovely Menantic Creek. An open plan affords great light throughout the living room which has a fireplace, dining area, and kitchen all overlooking an inviting covered porch and deck on the waterside. The main floor also has a comfortable family room and small bedroom plus bath. The second floor has a primary bedroom, a bath, and a third bedroom. A two car garage is being used as an additional game room and seating area. The property has a dock, a well landscaped drive, and ample parking. Located on the Menantic Peninsular not far from Wades Beach, the Island Boatyard Marina and Salt restaurant. Rental Registration # 2023-L-0020 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i72079428
Charming 6 bedroom Victorian on Shelter Island Sound. Eat-in-kitchen, dining room, master bedroom, and front parlor opening to waterside rocking chair porch. Four Craftsman Victorian bedrooms on second floor, one with a waterfront screened porch. Near ferry, beach club, and shops. Rental Registration # 2023-105L For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66793571
Located near a Town Landing on West Neck Creek for kayaking and paddleboarding, in the lovely Silver Beach area of Shelter Island, this 3 Bedroom, 2.5 bath home has an entry hall with half bath, living room with vaulted ceiling and fireplace, family room with door to small enclosed side porch, kitchen with breakfast bar, dining room, primary bedroom suite with private bath and two additional bedrooms with hall bath. The kitchen and living room have access to a big, beautiful screened porch with outside dining and seating. There is also a nice sun deck and big back yard. Rental Registration # 2023-L-0097 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i68915789
Located near Coecles Harbor and Sylvester Manor farm, this 3 ranch bedroom 3 bath ranch home has 2 newly updated bathrooms and central air conditioning. A great place to spend your summer days. Available Memorial daythru Labor or monthly. Rental Registration # 2024-L-0037 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i72278270
Lovely Hay Beach Home with Pool. Nicely appointed seasonal 4 bedrooms, 3 bath home with in-ground 9' diving pool awaiting your arrival. Spacious home on a shy acre with deck and patio for outdoor entertaining. Close to beaches, shopping, restaurants and ferries to both forks! Come to Shelter Island this summer and enjoy the natural beauty of it all~ Fire pit, gazebo, chairs, and lounges are included. Well-behaved dog-friendly home. Permit # 2023-V-0005 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67515977
Recently built, this exquisite and beautifully decorated farm house is located on a beautiful hill top with wonderful views of the tree tops. Located in an area close to the south ferry, this 4 bedroom house (all with en-suite baths) is a wonderful rental. Heated pool with a sunny patio would be the envy of all your summer guests. For those not so sunny days, enjoy a work out on the Peloton bike, a game of billiards or enjoy a movie night on the large screen TV. A must see. Price is for any two week period in July or August with dates negotiable. Rental Registration # 2023-L-0064 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67379404
Comfortable, charming cottage with central air conditioning and expansive family room with iron day beds for relaxation post a day at the beach. Blue stone patio with Brown Jordan furnishings and outdoor shower. Home has three bedrooms and two baths on a full acre. Outdoor hammock and specimen trees to gaze upon complete the picture. Home is on a private road with close proximity to the Ferry. Rental Registration # 2023-L-0116 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66964594
Beautiful home across the street from beach access, relax and unwind in this 4 bedroom 3 bath home steps to beach. Back deck off the dining room for additional entertaining space. Additional playroom on the lower level. The kitchen and baths are recently updated. Rental Registration # 2022v0017 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i69239657
19L-0065. Very charming with an open living room/beach stone fireplace, chef's kitchen with breakfast bar and access to a spacious sunny deck, familyroom, also with deck access, beautiful master bedroom with ensuite bath, 6' Jacuzzi tub and separate glassed shower plus a balcony deck. This bright, airy home offers 3 additional bedrooms and 2 additional baths to comfortably accommodate all plus new heated gunite pool and poolhouse with bedroom, bath, living room and kitchenette. Barbecue and dine on the deck, relax and read on the screened porch or take your bikes to Crescent Beach, town shops and ferry. Rental Registration # 2023-L-0019 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i69400504
Come and enjoy all Shelter Island has to offer. This lovely 3 bedroom home has been skillfully turned into the perfect summer spot with every amenity who could list! Gunite Pool, outdoor shower, covered seating area, pool house with bar, pool table and games area. Plenty of outdoor eating spaces, BBQ, herb garden, firepit, loungers and chilling spots including lovely front porch. Well stocked kitchen, open living area with fireplace and dining room, primary bedroom, guest with queen and a guest with bunk beds and 2 baths complete the first floor. Lower level has a movie area with projector. You may not leave the home but if you do there are numerous beaches to choose from, the Historic Heights stores, top class restaurants, nature preserve and ferries for adventures to Sag Harbor and Greenport! Rental Terms: Memorial Day - Labor Day: $60, 000 June: $15, 000 August - Labor Day: $28, 000 July: $20, 000 July - Labor Day: $45, 000 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66984781
Rental Registration # 2024-L-0016 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i70003151
Original Farmhouse in great location, offering complete privacy on 3.4 acres. Beautiful private large property overlooking nature preserve. First floor has a living room with fireplace, family/TV room with french doors opening up to the back gardens, dining room, and a beautiful updated kitchen with high open cathedral ceiling, plus a first floor half bath. Second floor has 3 bedrooms, 2 baths, and an office. Outside there is a Large screened in porch, outdoor dining area under covered pergola just off of the kitchen, outdoor shower, and tree house. Located just across from Coecles Harbor marina for boaters and close to Hay Beach. Rental Registration # 2023-L-0056 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i67263893
Within close proximity to sandy Hay Beach, this immaculate 4 bedroom, 4 bath cedar shingled three-level modern has the spirit of living in a birds nest with sliding glass doors and porches everywhere overlooking cherry trees and wrap around deck, bay breezes blow throughout gently. The kitchen is a chef's delight, with granite counters, maple cabinets, Viking stove, Monogram refrigerator, Bosch dishwasher, and sliding doors to an outdoor BBQ connected to nearly unlimited propane. The 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 / study 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. The heated Gunite pool has mahogany decking and lush bamboo gardens, sound system controlled through remote to the home and river stone paths. Gardiner's Bay Country Club just off the yard and sounds of the beach. With a popular rental history, this home has it all for a wonderful Summer vacation! Rental Registration # 2024-L-0019 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i68435583
Shelter Island waterfront 4 bedroom, 3.5 bath contemporary with extraordinary views toward West Neck Harbor. Located on a landscaped acre on a lovely, peaceful inlet, this two story home enjoys beautiful views from the main floor living room with fireplace and dining area, a stainless and granite kitchen with cherry cabinetry and primary bedroom ensuite, all of which have access to a spacious waterside deck, outdoor shower and green lawn leading down to the water that is perfect for kayaking and paddle boarding. The second floor rooms include 3 additional bedrooms and two baths, an office and comprehensive water views with a balcony deck running the length of the house. This inviting vacation home is conveniently located near sandy Wades Beach which has a lifeguard, facilities, ample parking and amazing sunset views. Rental Registration # 2022-L-120 For more details and to contact: https://realtyww.info/homes_shelter-island-d537329/for-rent_i66919113
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