Shelter Island NY Real Estate & Homes for Sale

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.

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.

Cool Modern with 4 bedrooms, 3 baths nestled on Bucolic Fresh Pond with waterside decks from 3 bedrooms including the spacious primary suite. Mature landscaping and lawn down a private driveway. Recently renovated and updated includes solar panels, new decks and IA septic system. The open floor plan has beautiful waterviews.

Cool Modern with 4 bedrooms, 3 baths nestled on Bucolic Fresh Pond with waterside decks from 3 bedrooms including the spacious primary suite. Mature landscaping and lawn down a private driveway. Recently renovated and updated includes solar panels, new decks and IA septic system. The open floor plan has beautiful waterviews.

COMING SOON!!! A wonderfully maintained contemporary with winter water views of Gardiner's Bay and year round views of the beautiful fairways of Gardiner's Bay Country Club. Bring your golf cart and clubs, it doesn't get any better then this for the golfer in your family. Situated near the 14th tee box of GBCC, the home has three bedrooms and three bathrooms. A chef's kitchen with stone countertops that opens to a light filled family room. The living room with a vaulted ceiling has a stone faced masonry fireplace. Plus, a lower level apartment/office with separate entrance, Large wrap around decks, a 30' x 15' vinyl swimming pool, lush gardens, 10' x 16' garden shed, and Koi pond with charming foot bridge. Exclusive: $1.9M.

TWO HEARTHS: STUNNING GREEK REVIVAL~ SHELTER ISLAND Discover your slice of perfectly preserved paradise on Shelter Island, with ample room for expansion and add your own brand-new pool. This impeccably preserved architectural masterpiece dates back to 1848 and stands as one of the four original Greek Revival homes on Shelter Island. Truly an unparalleled treasure. The appeal is instantly clear with charming colonial styling on the columned, wraparound porch. The interiors are well-equipped for luxury living and can easily be updated to accommodate many design possibilities. This intact residence, which boasts 3 bedrooms and 3 baths, sits on a generous 1.7-acre parcel in coveted C zone, offering boundless opportunities for expansion and enhancement. With period-accurate trim detailing, the existing structure lends itself beautifully to transformation. It leaves ample space for a potential guest house while still allowing for substantial upgrades, including the addition of a pool to the expansive backyard. Positioned against sprawling parcels, this property enjoys both privacy and proximity. Moments away, discover the allure of Sunset Beach Resort, the prestigious Shelter Island Country Club & Golf Course, The Perlman Music Program, The Pridwin Hotel & Cottages, and The Heights, ensuring a lifestyle enriched with leisure and culture. Best of all locations to be moments to Sag Harbor/Hamptons and/or the North Fork. Less than 2 miles to the South Ferry and 1.2 miles to the North Ferry. Don't miss your chance to own a piece of Shelter Island's history. Embrace the opportunity to craft your dream oasis in this unparalleled setting on the East End. C0-Exclusive: $1,999,999.

A water view vista of scenic Coecles Harbor could be all yours with this spacious well-maintained home built in 1979. The open living room with two story ceiling, wood burningfireplace and adjoining dining area with hard wood floors have access to a wraparound Mahogany deck to maximize the view. The current eat-in kitchen and separate pantry offer space to create a larger culinary feast. The main floor includes a primary suite consisting of two rooms:bedroom with fireplace and deck access; two bathrooms and an office/den with water view. Upstairs aretwo bedrooms with shared bath, one of the bedrooms has a private deck overlooking the water. A finished basement includes a wet bar and full bath and walk out sliding glass doors. A separate unfinished basement room has potential for a pool/lounge area. At 1.4 acres, there is ample room for a pool. The approach to the house is very private with a long gravel driveway and shrubbery surrounding the house and two-car garage. A fenced garden area and potting shed make for lush flowering in spring and summer months Set your sights on this home on the horizon. Heat: Propane/Hot Air, Taxes: $7,316.21

Discover this custom-built contemporary home nestled on 1.47 acres of serene beauty. Crafted with love, it boasts cedar siding, wide plank pine floors, and hand-hewn timbers. Approach through a meandering driveway, greeted by vibrant gardens and majestic trees-a perfect outdoor oasis. Inside, soak in the timeless charm of pine floors and abundant natural light. A passive solar design ensures energy efficiency. The allure doesn't end there; ascend to the second floor, a canvas awaiting your personal touch. With soaring 14-foot ceilings and Board of Health approval for a total of 4-bedrooms, the possibilities are endless to tailor this space to your unique vision and needs. Convenience meets coastal charm as this property is just moments away from the pristine shores of Crescent Beach, tantalizing restaurants, and eclectic shops.

Discover this custom-built contemporary home nestled on 1.47 acres of serene beauty. Crafted with love, it boasts cedar siding, wide plank pine floors, and hand-hewn timbers. Approach through a meandering driveway, greeted by vibrant gardens and majestic trees-a perfect outdoor oasis. Inside, soak in the timeless charm of pine floors and abundant natural light. A passive solar design ensures energy efficiency. The allure doesn't end there; ascend to the second floor, a canvas awaiting your personal touch. With soaring 14-foot ceilings and Board of Health approval for a total of 4-bedrooms, the possibilities are endless to tailor this space to your unique vision and needs. Convenience meets coastal charm as this property is just moments away from the pristine shores of Crescent Beach, tantalizing restaurants, and eclectic shops.

Sun-drenched living unfolds in this 2.16-acre south-facing haven, where light bathes a charming Hampton's-style shingled home. Relax by the sparkling Gunite pool, accessible through expansive glass doors from the 2-story living room, warmed by the soaring fireplace. Unleash your inner chef in the spacious kitchen, boasting shaker-style white cabinets, gleaming quartz counters, and top-of-the-line stainless steel appliances. The adjoining family room beckons with its cozy gas fireplace and seamless access to the patio, perfect for effortless entertaining. Unwind in one of 6 bedrooms, each offering a peaceful escape. Indulge in self-care in 6 full and 2 half baths. The partially finished lower level presents additional flexibility with 2 bedrooms, 2 baths, and living area, ideal for guests or a media room. The 2-car garage is directly connected to the kitchen. Escape to charming Sag Harbor in mere minutes, with the South Ferry just .5 miles away. Make idyllic Shelter Island your home.

Sun-drenched living unfolds in this 2.16-acre south-facing haven, where light bathes a charming Hampton's-style shingled home. Relax by the sparkling Gunite pool, accessible through expansive glass doors from the 2-story living room, warmed by the soaring fireplace. Unleash your inner chef in the spacious kitchen, boasting shaker-style white cabinets, gleaming quartz counters, and top-of-the-line stainless steel appliances. The adjoining family room beckons with its cozy gas fireplace and seamless access to the patio, perfect for effortless entertaining. Unwind in one of 6 bedrooms, each offering a peaceful escape. Indulge in self-care in 6 full and 2 half baths. The partially finished lower level presents additional flexibility with 2 bedrooms, 2 baths, and living area, ideal for guests or a media room. The 2-car garage is directly connected to the kitchen. Escape to charming Sag Harbor in mere minutes, with the South Ferry just .5 miles away. Make idyllic Shelter Island your home.

Situated on a shy acre, is a beautiful traditional, Hampton's style shingle home. With over 5000 sq. ft. of living space on mostly one level, this home has it all. The grand foyer welcomes you with vaulted ceilings and opens into the living room with wood burning fireplace. The chef's kitchen offers luxury appliances, large island, granite counters, wet bar and breakfast area. Most rooms lead to the rear courtyard, with patio, wood burning fireplace and heated Gunite pool. The primary bedroom en-suite and the separate guest wing with den and fireplace creates an estate like feeling. This property is centrally located and minutes to beaches, shops, dining, school and ferries to both the Hamptons and the North Fork.

Situated on a shy acre, is a beautiful traditional, Hampton's style shingle home. With over 5000 sq. ft. of living space on mostly one level, this home has it all. The grand foyer welcomes you with vaulted ceilings and opens into the living room with wood burning fireplace. The chef's kitchen offers luxury appliances, large island, granite counters, wet bar and breakfast area. Most rooms lead to the rear courtyard, with patio, wood burning fireplace and heated Gunite pool. The primary bedroom en-suite and the separate guest wing with den and fireplace creates an estate like feeling. This property is centrally located and minutes to beaches, shops, dining, school and ferries to both the Hamptons and the North Fork.

A great opportunity to own a home in business zone, room for expansion and business. 3 Bedroom, 2 and 1/2 bath on .72 acres. Centrally located ,great for business exposure.

Water view second floor condo. Open concept living, with two rooms. Stepping over the threshold into the first room one finds a bathroom to the right with double sinks and full closet. The second room with water views serves as a living, dining room with kitchenette. A slider opens onto a private balcony overlooking Dering and Greenport Harbors. Space for a table with chairs. Unit has designated personal storage in basement.

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.

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.

HARBOR VIEW ESTATES: Private community with deeded beach rights. Three to four bedrooms, two baths, study, fireplace, living room, open kitchen, full basement, decks, heated gunite swimming pool, detached two garage garage. Exclusive: $1.585M. Please call Angelo at Dering Harbor Real Estate.

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.

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.

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.

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.

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.

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.