Shelter Island NY Real Estate & Homes for Sale

Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom with balcony is as dreamy as the view, which is truly incredible. An oversized bath and additional upper-level bedroom complete this private owner's area. Two main level bedrooms serviced by a full bath will accommodate family and friends beautifully. A two-car garage and studio with a half bath is a great place to set up your game room or home office. A full basement with high ceilings can be finished to incorporate an exercise or workout room. Lush landscaping with charming stone walls on 1.90 acres completes this peaceful location.

Step into timeless elegance with this iconic single-family residence with an option for an owner-occupied 5-bedroom bed & breakfast (B&B) license. Originally constructed in 1902 and beautifully reimagined to meet modern standards. Nestled in the serene Shelter Island Heights, 7 Stearns Point Road offers an exquisite blend of historic charm and contemporary luxury. This expansive property sits on a 0.70- acre parcel, equipped with 5,838 +/- sq. ft. of living space, plus a spacious basement level adding 2,588 +/- sq. ft. The property features 7 ensuite bedrooms complemented by 2 large living rooms and a well-appointed kitchen. Recent renovations have expanded the living space to include an extension with 2 additional bedrooms, a stunning double-height Great Room, as well as a state-of-the-art gym/yoga studio. Enjoy the beautiful backyard with a heated 40x18 in-ground Gunite pool, perfect for relaxing after a day exploring the nearby Crescent Beach and Sunset Beach which is moments away. The property also includes a full liquor license, which enhances its appeal as a premier vacation destination. The spacious basement areas provide ample storage and laundry facilities, ensuring convenience. A wonderful investment opportunity for an owner-occupied 5-bedroom bed and breakfast. The property also includes 2 driveways. Key Features: - Historic property built in 1902, fully renovated - 9 bedrooms and 9 bathrooms, including recent additions - Option for an owner-occupied 5 Bedroom bed and breakfast - Two driveways - Heated 40x18 in-ground Gunite pool - State-of-the-art gym/yoga studio - Full-height basements for storage and laundry - Walking distance to Crescent Beach & Sunset Beach - Full liquor license

Step into the grandeur of this lovingly restored Historic Tudor home, a masterpiece built in 1901. Impeccable craftsmanship defines this 6-bedroom, 4.5-bathroom residence, where history meets modern luxury. The home boasts 6 meticulously restored fireplaces, each upgraded with heatilators for efficient warmth. The plaster has been refurbished, preserving its original charm. Additional insulation on the 2nd and 3rd floors ensures comfort and energy efficiency. A chef's dream, the kitchen has been completely renovated and now includes a newly added butler's pantry. New heating and central AC systems have been installed throughout, ensuring year-round comfort. Outside, the property is adorned with a new heated 20 x 50 Gunite pool and hot tub, complemented by a classic brick patio that enhances the elegance of the estate. A generous deep water dock accommodates multiple boats, perfect for those who cherish waterfront living. A rare opportunity to own a piece of architectural history.

Don't miss this exceptional opportunity and great value to own a special slice of heaven down a private lane close to Shelter Island Country Club, Sunset Beach, Shopping, Restaurants and more. This 4 Bedroom 2 1/2 Bath sits on over 1.2 beautiful acres with mature trees and expansive lawns Creating a peaceful retreat. Room for majestic pool and guest house. Has attached garage and full basement for ample storage. Additional features include 2 storage sheds for added convenience. This well-located property makes the ideal sanctuary for relaxation and leisure.

Welcome to this stunning Ranch nestled in the serene and sought-after neighborhood of Silver Beach on an impressive .87 acre lot with beach rights. This meticulously maintained residence offers a perfect blend of modern comfort and timeless elegance. Upon entering, you're greeted by an inviting living room accentuated by gleaming hardwood floors. The spacious living area seamlessly connects to the chef-inspired kitchen, complete with sleek stainless steel appliances, granite countertops, and ample cabinetry - an ideal setting for culinary enthusiasts and entertaining guests. Just off the dining area is a sunken enclosed sun room, insulated for all seasons. This tranquil area provides ample natural light and generous space for another living space or dining area. Two of the exterior walls are made up with floor to ceiling windows. Allowing for one to be completely surrounded by nature. Another key highlight of this home is its captivating outdoor space. The private backyard is perfect for relaxation or gatherings, with a well-manicured garden and a charming lounge area - an ideal spot for al fresco dining or enjoying the picturesque views.

Ultimate serenity & potential to expand await you on these scenic 5.5 acres at the end of a 1000' private driveway. Expansive Artist's studio w/wall of windows on 1st floor & apartment with separate entrance above. Elegant, elevated in-ground pool with commanding view of rolling lawns, woods, vegetable & perennial gardens, fruit trees & large stocked man-made pond. Conveniently located less than a mile from South Ferry & a short distance to Wades Beach & Mashomack Preserve.

Indulge in coastal living at its finest with this meticulously maintained one-level home in a charming beach community. Renovated in 2012 by Fokine Construction, this home offers stunning water views of Menantic Creek from most rooms. The open-plan layout features a vaulted living room with fireplace, dining area, and a custom chef's kitchen. Step onto the water side deck for a serene outdoor retreat with mahogany railings and stainless wire. The primary bedroom boasts two walk-in closets and a luxurious en-suite bathroom. Enjoy the tranquility of the 1.29-acre shared parcel extending into the creek. This quiet enclave offers the perfect blend of luxury and natural beauty for coastal living at its finest. The shared parcel is 50% ownership of 3 Hagar Rd 700-18.-3-41, 1.29 acre vacant parcel. 1/2 taxes =$1,280.62

Enjoy this inviting ranch-style home just blocks from Bootlegger's Alley beach access and beautiful sunsets. Featuring an open plan with country kitchen, dining area, living room, and den, this home offers seamless living and entertaining. Warm up by the cozy wood-burning fireplace or relax in the spacious yard with a deck overlooking serene views and glimpses of Westmoreland Mill Pond. Enjoy the Gunite inground pool with patio surround for summer refreshment. Perfect for enjoying sunsets and island living, this home combines comfort with outdoor leisure.

No details spared in this impeccably renovated Village Classic 4-bedroom spacious home with water views of Chase Creek in the heart of Shelter Island Heights and down the street from shops, restaurants, The Chequit Hotel, Eccentric Bagel, Stars Caf?, Marie Eiffel, Leon 1901, Sunset Beach, Shelter Island Golf Club and more. The first floor graciously flows from the living room with new raised fireplace with custom floating stone seating to the dining room that provides peaceful and commanding water views of Chase Creek both in the morning and at sunset. The new Henrybuilt kitchen, custom Bosch appliances, and hidden wine refrigerator in bar area leads out to the inviting rear Ipe and Mahogany screened-in-porch constructed in 2023 overlooking Shelter Island Golf Club. Freshly installed 8" wide plank white oak floors extend throughout main floor. The ensuite primary bedroom with a recently renovated bathroom and an additional powder room complete the first floor. Re-envisioned railings and stairways lined with custom designed runners lead up to the second floor and lower level. The second floor includes 3 spacious, light-filled bedrooms and a bath while the lower level has walls of ground level windows looking at Chase Creek and gardens, also a perfect option for a future ground level walk-out to the proposed pool. Mature landscaping provides privacy and serenity. Enjoy the benefits of Community Tennis and access to The Shelter Island Heights Beach Club. Kayak or paddle board on the island from one of the many beaches and inlets. Close to both the North Ferry to Greenport and 34 Vineyards on the North Fork and not far from the South Ferry to Sag Harbor, the Hamptons and Ocean Beaches. ??

This split level home with 1.47 acres is located in the silv er beach area of Shelter Island. When you walk into the home you are invited into the main room of the home with large vaulted ceilings and an open airy concept. There are 2 bedrooms with 2 bathrooms on the upper level and 1 bedroom and bathroom on the lower level. The backyard has a large heated gunite pool to enjoy with a pool house that has a living room, half bathroom and a gym. The added bonus to this property is that it has a tennis/basket ball court which is hard to find on Shelter Island.

Move in and immediately enjoy this elegant Colonial home on an expansive parklike property with all the amenities you have dreamed of. The bright, open and airy main floor features 9 foot ceilings. a spacious living room with wood burning fireplace, gourmet kitchen with high end appliances and large ground floor primary suite. Outside enjoy multiple outdoor living destinations; entertain on the living room like bluestone covered front porch, lounge by the heated gunite pool with travertine surround, enjoy a good book or barbecue on the back deck or relax with friends around the firepit. A short distance down the private road is your private waterfront parcel complete with a large dock perfect for launching your power boat, paddleboards and kayaks or enjoying sunset and "docktails" on your floating lounge. The second floor of the home is perfectly appointed for family and guests with four generously sized bedrooms in two wings separated by a bonus living room. A separate, detached two story carriage house sits nearby and has room for two cars or a large exercise room on the ground floor and a spacious studio with vaulted ceiling, full bath and kitchenette on the second floor. Centrally located on a quiet private road this tranquil property feels away from it all and yet you are within close proximity to everything, restaurants, Dering Harbor Village and sandy beaches. This beautiful home is the luxurious retreat you have been looking for to enjoy leisurely days on this magical island.

Escape to tranquility in this beautiful contemporary home nestled on Shelter Island. Built in 1993, this 3-bedroom, 3.5-bathroom residence boasts 2,460 square feet of meticulously crafted living space, perfectly positioned to capture breathtaking water views from nearly every room. Upon entry, you're greeted by the inviting ambiance of the great room, featuring a majestic gas fireplace and expansive windows framing panoramic vistas of the tranquil pond. Sliders invite you to step outside onto the deck, where you can savor morning coffee or entertain guests against the backdrop of serene waters. Adjacent to the great room, a screened porch awaits, providing a peaceful retreat for relaxation in the cool breeze. Close Proximity to Wades Beach and less than a mile to South Ferry, just a short distance to the Hamptons.

Nestled amidst the serene beauty of Shelter Island, this stunning residential home presents an unparalleled opportunity for those seeking a tranquil retreat. Boasting breathtaking water views of Miss Annie's Creek in the renowned Mashomack Preserve, this residence seamlessly blends relaxation with pristine natural surroundings. As you step onto the property, you're greeted by the charm of covered porches, and heated pool, inviting you to unwind and soak in the picturesque vistas that stretch as far as the eye can see. Whether you're savoring your morning coffee or hosting intimate gatherings with loved ones, these serene outdoor spaces provide the perfect backdrop for every occasion.

This lovely ranch located in Hay Beach on 1.06 Acres, is in an ideal setting, close to beaches and golf courses. Boasting 3 bedrooms and 2.5 baths, one of which is the primary ensuite bedroom with a walk-in closet, providing comfortable accommodation. This spacious home features an eat-in-kitchen illuminated by a skylight, cathedral / vaulted ceilings, hardwood floors, a pantry, and powder room, home office, a formal dining room, and an inviting living room with fireplace, and sliding glass doors leading to an outdoor deck. The outdoor area is perfect for enjoying the serene surroundings. Additionally, there is a full basement, partially finished, and a spacious 2-car garage. With all these amenities and priced to sell this property presents a wonderful opportunity for prospective buyers.

The ultimate sunrise and sunset views adorn this special waterfront 3 bedroom home on Mabel's Creek overlooking Shelter Island Sound and the Shelter Island South Ferry route to and from Sag Harbor's North Haven. Sit outside and renovated 2 story cottage/beach house getaway with water views from most rooms in the house on a quiet street ending at a private Shorewood Association boat launch access to the Shelter Island Sound. Available when living in Shorewood, are community tennis courts, beach access and boat launches and mooring rights. Take a cruise on your kayak, paddle board or boat directly from your private access onto Mabel's Creek from the back yard. A private boat dock is also a possibility. This is a one-of-a-kind must see property for the low-key buyer who dreams of bucolic waterfront vistas and color-filled skies each and every morning and evening while enjoying breakfast or dinner on the water facing patio or read a novel while relaxing amidst the water's waves. Do a cheese tasting at White Oak, bear tasting at thee Shelter island brewery or wine tasting at the many new restaurants on Shelter Island including The Rams Head Inn, Leon1909, The Pridwin Inn, The Chequit, play a round of golf at the Shelter Island Golf Club and Flying Goat Restaurant or watch the sunsets over Crescent Beach at the famous Sunset Beach. So close to Sag Harbor on the South Fork are shops, restaurants and Bay Street Theater while Sagaponack and Bridgehampton have pristine white sand ocean beaches, farmland, Wolffer Estate Stables and Vineyard, and world class private golf courses on the South Fork or head to Greenport via the North Ferry for a day on the North Fork touring over 33 wineries, farm stands, shops and restaurants.

In our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3,800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage.

Presenting Shelter Island Farm. Just completed and spread across acres of historic Shelter Island farmland, words cant begin to describe this new construction farm style estate from Wall Street Journal "House Of The Year" developers, Mike & Kerry Gaynor. Come visit Shelter Island, have lunch at one of our many new hotels and restaurants and schedule your private tour of this stunning new estate. There is absolutely nothing else like it anywhere on the market.

Modern luxury meets tranquility in Hay Beach. This exceptional 3-bedroom, 3-bath Modern Ranch nestled in Hay Beach's wooded haven offers an escape from the ordinary. Step inside and be greeted by an open floor plan, seamlessly connecting the living room, dining area, and a chef's dream kitchen. High-end appliances from Bosch, Liebherr, and Viking shine within custom Levante wood cabinetry and granite countertops. Unwind in Your Private Backyard Paradise. Be captivated by the home's breathtaking gardens surrounding the inviting in-ground pool and hot tub. This fully renovated, turnkey oasis awaits you - move in and start relaxing today!