$60,000 per month
16 Little Ram Island Dr, Shelter Island, NY 11964
In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful water views overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sits at the end of a long winding driveway providing great privacy. There has been a new kitchen renovation now providing water views while cooking.
$30,000 per month
15 S Cartwright Rd, Shelter Island, NY 11964
Located on the southern side of Shelter Island within close proximity to beaches and boating, this house has been completely renovated with all modern amenities in place. The entry porch leads you into the great room, which includes the kitchen, dining, living and lounge area. The kitchen and dining area are open plan and lead out to the pool, garden and expansive fenced garden. The bedrooms are
Michael Brennan Douglas Elliman Real Estate
$50,000 per month
37 Tuthill Dr, Shelter Island, NY 11964
WHEN AN ARTIST MAKES A HOME Serena Dugan, Co-Founder of Serena&Lily has completed her renovation of 37 Tuthill Drive, Shelter Island. This property is a robust representation of Serena's vision as an artist and a designer. Each detail was carefully considered and selected, and her point of view is visible throughout the house. The artwork, fabrics, and wallpapers are of her design. In some
$50,000 per month
28 Gardiners Bay Dr, Shelter Island Heights, NY 11965
Experience the ultimate in tranquility and luxury at this secluded oasis, where every moment is a picturesque escape. Discover breathtaking panoramic water views and soak in the mesmerizing sunrise & sunsets over Gardiner's Bay from just about every room in the house. Boasting an impressive layout featuring an open plan den/media room, dining room, and chef's kitchen-all thoughtfully designed to
Michael Brennan Douglas Elliman Real Estate
$30,000 per month
28 Cobbetts Ln, Shelter Island, NY 11964
Secluded 3+ bedroom, 2.5 bath contemporary on 1.5 beautiful acres with new gunite, heated pool. Common rooms include open plan living room with soaring ceilings and fireplace, comfortable dining area and kitchen with new appliances. The primary bedroom suite has a king bed and full private bath. All overlook a back expanse with deck, fenced pool and gorgeous trees. A tv media room is also on
$18,000 per month
5 Bay Ave, Shelter Island, NY 11964
Open plan beach house with superb water views located in the highly sought after Montclair Colony. Centrally located near markets and many conveniences, there is much to adore in this home. Open plan living room with sunroom, dining and eat in kitchen. This home offers two bedrooms with two full baths and another bedroom with a full bath over the two car garage. In addition the master bedroom has
Michael Brennan Douglas Elliman Real Estate
$29,350 per month
13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964
Welcome to Sandpoint, an exclusive Shelter Island retreat nestled on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds.
$14,000 per month
3 Lakeview Dr, Shelter Island, NY 11964
Wake up each morning to the sweet sounds of birdsong in this charming 4-bedroom, 2-bath, nestled amongst rolling hills. Located .6 miles from coveted Wades Beach and Mashomack Preserve. This secluded property feels like a private sanctuary, surrounded by lush greenery, blooming trees, and vibrant summer flowers. The open-concept living-dining-kitchen area is perfect for entertaining, with a
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$12,000 per month
103 S Midway Rd, Shelter Island, NY 11964
Beautiful Wades Beach and West Neck Harbor just a few doors down from this lovely one acre plus landscaped property with tennis court. This recently renovated 3 bedroom, 2.5 bath home features an open layout which includes a living room with fireplace and front deck access, spacious great room with new streamlined kitchen, breakfast bar and new appliances; a dining area with skylights and access
$30,000 per month
104 S Ferry Rd, Shelter Island, NY 11964
2025 Rates: June $30,000, July $60,000, August $65,000, July-August $125,000 and MD-LD $150,000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant
Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
$18,000 per month
44 Lake Dr, Shelter Island, NY 11964
Wades Beach area contemporary home on serene and lovely Fresh Pond. Beautifully landscaped with charming stone walled gardens and amazing expansive sunset views of lake-like Fresh Pond from most rooms of this 2 bedroom, 3 bath renovated home. Stairs from the driveway lead to an elevated entry and first floor. Entry foyer opens to a large inviting living room with vaulted, beamed
$75,000 per month
15 Montclair Ave, Shelter Island, NY 11964
Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a
Margot Reutter Corcoran
$55,000 per month
12 Cove Way, Shelter Island, NY 11964
This house is the summer retreat you have been looking for. Centrally located down a private lane you will enjoy extraordinary views of the creek from the poolside patio. Private dock on this waterfront property for all the summer activities, just feet from the back door. This home offers a large chefs kitchen open to the living, dining and reading nook. Windows galore inviting the natural light.
$50,000 per month
21 Peconic Ave, Shelter Island, NY 11964
Impeccable cottage ideally located in the heart of Silver Beach. Very Closeto the secluded association beach and a short distance to Shell Beach. Lovely deck with water view and cool summer breezes. Three bedrooms and two bath. Ref. R103 MD - LD $50,000 June - LD $50,000, June $10,000, July $20,000, and August $25,000
Melina Wein M WEIN REALTY INC
$40,000 per month
6 Cobbetts Ln, Shelter Island, NY 11964
An incredible property with everything you need for a fantastic summer vacation. This 5-6 bedroom, 5 bath home features a spacious, open living room with fireplace, dining area, charming eat-in country kitchen, media room, waterview deck, wrap brick patio, heated pool, tennis court and small strip of beach! All on 3 acres with stunning waterviews. Available for winter rental. [[Rental
$25,000 per month
21 Peconic Ave, Shelter Island, NY 11964
Discover summer on Shelter Island in this newly renovated and beautifully furnished 3 bedroom two bath cottage , with wrap around decks overlooking Peconic Bay and evening Sunsets. Located in this quiet community with Beaches directly across from your house this is Summer as you remember it. The open floor plan of the house provides great spaces for family and friends to enjoy meals and gather
$30,000 per month
55 N Cartwright Rd, Shelter Island, NY 11964
This original 4 bedroom Shelter Island Farmhouse is located on the perfect 3.4 acre setting. offering complete privacy. A beautiful large property overlooking a nature preserve is the perfect place to slow down and hang out with family and friends, for a Summer of peace and relaxation. Evenings on the screen porch, bonfires, napping in the hammock, or games of croquet it's all here. The First
$38,500 per month
91 Shore Rd, Shelter Island, NY 11964
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
$12,000 per month
6 Crab Creek Rd, Shelter Island, NY 11964
It all about the sandy Peconic Bay beach and stunning maze of creeks at the end of this quiet street. Create wonderful summer memories in this open and comfortable cottage. After a fun day at the waters edge unwind in the bright and airy sun-room with easy access to large deck and peaceful yard. Living room with high ceiling, skylights and fireplace flows into dining room and kitchen providing
$24,000 per month
9 Country Club Dr, Shelter Island, NY 11964
This open and bright 3 bedroom 2 Bath with heated pool is the perfect summer escape. Enjoy strolls on beautifully preserved Menhaden Beach from this quiet enclave. The house features central air, outdoor shower, finished lower level, comfortable outdoor areas with decks and patios, Pet considered [[Rental Registration # 2023-L-205]]
$31,000 per month
17 Stearns Point Rd, Shelter Island, NY 11964
Located within close proximity to popular Sunset Beach, golf, tennis and Perlman Music Camp in desirable resort area, this hand-crafted Scandinavian style farmhouse with summer guest cottage and barn with loft on 1.5 acres was thoughtfully built and completed in 2010 using rich textures and environmentally efficient amenities. Pine and cedar aromas fill the air inside this beautifully sunlit
$35,000 per month
20A N Cartwright Rd, Shelter Island, NY 11964
RR# 2025-L-2026 Down a long private driveway is this contemporary 4 bedroom 3 bath home with heated pool. With bedrooms on 3 floors, there is room for all. Large decks and patios for entertaining abound this August rental. Located in the center of the island, this wonderful rental is a minute to all that Shelter Island has to offer. A must see. [[Rental Registration # Pending]]
$45,000 per month
34 Country Club Dr, Shelter Island, NY 11964
Located on the Gardiners Bay Country Club, this gorgeous newly built home features an open living room, dining room and wonderful high end kitchen. Bedrooms feature en-suite baths and are all tastefully decorated. This open layout is wonderful for entertaining, from the kitchen to the covered porches overlooking the heated pool and GBCC beyond. For further enjoyment, there is a pickleball
$55,000 per month
4 Bay Ave, Shelter Island, NY 11964
This clean and modern harborfront home is located in an area that features glorious sunsets. There are lovely gardens and shade trees with meditation areas to read or relax in, and the main home offers an open floor plan, with an L-shaped living room that maximizes views of the water, a fireplace for chilly nights, dining area overlooking the water, and efficient kitchen. There is a first floor
$45,000 per month
9 Sandpiper Rd, Shelter Island, NY 11964
Just a few minutes from Wades Beach is this private park-like enclave with a charming 2+ bedroom,1.5 bath shingled home, brand new heated gunite pool and beautiful new cottage with BR, bath, kitchenette, living room and dining area. 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
$50,000 per month
14A Heron Ln, Shelter Island, NY 11964
Stylishly renovated beach house with spectacular sunrise to sunset water views on a sandy beach. Set on West Neck Harbor with 3 waterside ensuite bedrooms plus a study with convertible sofa and 4 bathrooms in all. In a lovely setting well off the main road, the house has an enclosed stone courtyard leading to the glassed entry which opens on to a spacious common area with views of the water
$37,500 per month
2 Hagar Rd, Shelter Island, NY 11964
Short term rental! Available August 17 to September 1 at $20,0000. 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
$26,000 per month
71 Gardiners Bay Dr, Shelter Island, NY 11964
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 # 2025-V0002]]
$20,000 per month
70 S Ferry Rd, Shelter Island, NY 11964
Stunning renovation of this ultra charming c. 1822 historic Shelter Island farmhouse. Completely redone for every modern convenience while maintaining the integrity of the original dwelling with great attention to period and detail. This beautifully landscaped acre plus property has an expansive, hedged pool area with new gunite pool, and a bluestone patio with seating and dining areas plus
$15,000 per month
10 Crescent Way, Shelter Island, NY 11964
This 4 bedroom 3 and a half bathroom awaits your summer vacation. Perfect for families, entertaining, and relaxing. The first floor features 3 bedrooms including a guest suite. Additional 2 bedrooms with a shared bath and a half bath. The eat in kitchen, living room with cathedral ceilings and dining room blend for seamless entertaining. The second floor features a private primary ensuite
$90,000 per month
15 Montclair Ave, Shelter Island, NY 11964
Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a
$39,000 per month
37 Gardiners Bay Dr, Shelter Island, NY 11964
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
$32,000 per month
63 S Menantic Rd, Shelter Island, NY 11964
This newly renovated Shelter Island gem features green lawns, private beach and dock. Newly renovated, the house is clean and airy with beautiful light from windows overlooking West Neck Harbor. The kitchen opens onto waterside deck for sunset dinners and evening breezes. Open living/dining space with two additional rooms on the first floor for quiet reading or movie watching. Additional office
$69,000 per month
32 Hilo Dr, Shelter Island, NY 11964
This wonderful traditional has been totally remodeled and is a wonderful August rental. Four bedrooms, 3 with the most beautiful water views, and 4 and a half remodeled baths as well as a remodeled kitchen is the type of summer rental one is always dreaming of. Located on a water front bluff in Hilo Shores, sip cocktails on the veranda overlooking the pool and West Neck Bay in the distance. If
$70,000 per month
82 N Cartwright Rd, Shelter Island, NY 11964
Flooded with sunlight, this beautifully furnished 4 bed 3 bath home offers ultimate privacy on 3/4 acres. Completely updated with all new bathrooms and kitchen. The Chef's kitchen is designed with a spacious dining area for large gatherings. Primary en-suite has its own deck leading to the the pool and back garden. The other bedrooms are located at opposite ends of the house offering complete
$35,000 per month
50 Country Club Dr, Shelter Island, NY 11964
Sited on a gentle rise, minutes from Menhaden Lane beach, the stunning, Philip Johnson's Glass House inspired restoration of this Mid Century Modern home, has brick flooring throughout the main floor and an abundance of natural light. The home has splendor with the added benefits and comforts of today's amenities. Three bed three bath, with the den converting into the fourth bedroom/ private
$50,000 per month
151 N Ferry Rd, Shelter Island, NY 11964
This stunning 5 bedroom, 4.5 bath home has 6 acres and easy access to Dering Harbor Marina, the Shelter Island Yacht Club, Town dock, ferry, tennis, shops and restaurants in picturesque Shelter Island Heights. The house has first and second floor verandas, a center hall foyer, flanked by the living and dining rooms with a family-room, fireplace, powder room, marble and stainless kitchen and mud
$18,000 per month
6 Summerfield Place, Shelter Island, NY 11964
Charming Summer Victorian on Water. The peaceful living room and dining room are surrounded by the stunning waterfront porch The open and comfortable eat-in-kitchen and family room are comfortable essentials to this easy living home. First floor bedroom with full bath along with five craftsman's bedrooms and waterfront screened in porch on the second floor completes this charmer! Near
$15,000 per month
3 Crab Creek Rd, Shelter Island, NY 11964
Prime Location is Silver Beach, 3 bedroom 3 bath home situated on 1.27 acres with heated gunite pool with bluestone patio and outdoor shower and Tennis/ pickleball court. There is a pool house with a half bath features a lounge area and a gym. Recently renovated and turn key.Located a short distance to Silver Beach Association beach. [[Rental Registration # 2024-L-0052]]
$25,000 per month
14 Montclair Ave, Shelter Island, NY 11964
Located in Montclair Colony on the southwest corner bring your boat to your own private dock. Watch the sailboats go by and enjoy fantastic sunsets. [[Rental Registration # 2025-L-0013]]
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Shelter Island in Long Island is a 20-square-mile community accessible only by ferry, fostering a close-knit atmosphere where everyone knows each other. The island is surrounded by water, featuring beaches like Sunset Beach, which are popular for swimming, kayaking, and boating without the worry of big waves. One-third of the island is preserved by the Nature Conservancy, with Mashomack Preserve offering 2,000 acres of woods, marshes, bays, and hiking trails. Wildlife, including deer and over 200 species of birds, can be found here. Golfers frequent the Shelter Island Country Club and Gardiner’s Bay Country Club, while boaters often join the Shelter Island Yacht Club. Homes typically have spacious yards and range from Colonials with wood shingles to modern-style houses. The crime rate is lower than the national average, contributing to a peaceful environment. Shelter Island School, serving kindergarten through 12th grade, has a high rating and a low student-teacher ratio. The dining scene is vibrant, especially in summer, with popular spots like Stars Café, Vine Street Café, and SALT Waterfront Bar & Grill. Essential services include a grocery store, fish markets, and a seasonal farmers market, though there is no hospital on the island. Accessibility can be challenging due to reliance on ferries and the lack of mail delivery and garbage pickup. The South Ferry connects residents to the North and South Fork of Long Island, with further travel options to New York City.
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