luxury houses for sale Shelter Island, United States

Some properties are simply irreplaceable. This is one of them.nnHeld by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved.nCustom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island Shingle beach house sits on a level acre along one of the Island's most coveted stretches of waterfront 190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour.nnDeceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. Two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy.nnThe expansive side lawn often mistaken for a separate lot offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow.nnA chance to own a piece of Shelter Island's story.

Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island shingled beach house sits on a level acre along one of the Island's most coveted stretches of waterfront -190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Maturenlandscaping on all sides for privacy. The expansive side lawn is often mistaken for a separate lot and offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow.nA chance to own a piece of Shelter Island's story.

Some properties are simply irreplaceable. This is one of them.nnHeld by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved.nCustom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island Shingle beach house sits on a level acre along one of the Island's most coveted stretches of waterfront 190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour.nnDeceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. Two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy.nnThe expansive side lawn often mistaken for a separate lot offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow.nnA chance to own a piece of Shelter Island's story.

Some properties are simply irreplaceable. This is one of them. Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island Shingle beach house sits on a level acre along one of the Island's most coveted stretches of waterfront - 190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. Two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy. The expansive side lawn - often mistaken for a separate lot - offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow. A chance to own a piece of Shelter Island's story.

Rare opportunity to own .62 Acres of waterfront buildable land along West Neck creek, offering a beautiful setting with water views and direct access to the shoreline. Nestled within the peaceful Silver Beach community, this private and tranquil property is surrounded by nature and offers an exceptional opportunity to create a waterfront retreat. Across the water, protected preserved land ensures that the natural setting and peaceful views will remain undisturbed, adding to the property's sense of privacy and tranquility. Buyers should conduct their own due diligence regarding zoning, permits, wetlands, building potential, waterfront regulations, and all other applicable requirements.

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

Architecturally distinctive and deeply connected to its coastal setting, 126 South Midway Road is a private compound that captures the spirit of Shelter Island's artistic legacy. A private sanctuary comprising a four-bedroom main residence, a dedicated large art studio, and an independent two-bedroom casita, the property is thoughtfully arranged to maximize natural light, privacy, and sweeping water views. The architecture recalls relaxed modernism of iconic beach houses, an approach rooted in simplicity, creativity, and a fluid relationship with the landscape. Clean lines, a sleek pool and an intuitive indoor-outdoor flow create spaces that feel both intentional and effortlessly livable, ideal for a design-minded coastal lifestyle. The separate studio enhances the compound's creative sensibility, offering a quiet, light-filled environment for work or reflection, while the two-bedroom casita provides comfortable, private accommodations for guests or extended stays. Together, the structures form a cohesive yet flexible retreat, equally suited to intimate living and hosting. Comprised of 3,400 sq. feet living space across 3 levels in the main house plus additional storage, an expansive art studio of 1,400 sq. ft and 2-bedroom Casita living 1,140 sq feet with multiple decks and outdoor entertaining spaces this incredible compound is moments from Wades Beach. The property offers a rare combination of architectural character and proximity to one of Shelter Island's most celebrated shorelines. Longtime Shelter Island residents David Rankin OAM and Lily Brett OAM, both internationally recognized for their contributions to the visual arts and literature, have stewarded the home with a deep appreciation for creativity and place. (OAM denotes the Order of Australia Medal, a national honor recognizing distinguished contribution.) A compelling offering for those drawn to thoughtful design, privacy, and coastal modernism, 126 South Midway Road is a singular Shelter Island retreat.

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

New to the market, On The Bluff in North Haven, a beautiful waterfront home offering privacy, sweeping views from every vantage point, plus beauty and tranquility. Situated on 2 +/- acres, the 5,500+/- sq. ft. light-filled home offers 5 bedrooms, bathrooms, and ample entertaining spaces indoor and outdoor. The gunite waterside pool, finished lower level, 2-car garage and private beach access make this truly a very desirable home and property. First time offering exclusively at $6.9M.

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .44-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

Extraordinary North Fork Bayfront Estate on a Private Peninsula on Paradise Point, Southold- Welcome to one of Southold's most exceptional waterfront offerings, a spectacular bayfront estate set on a private 1.6-acre peninsula within the coveted Paradise Point community. Surrounded by water on three sides and boasting an extraordinary 335 feet of Bayfront shoreline and private dock in a protected boat basin, this remarkable property captures sweeping panoramic views across Southold Bay to Shelter Island and beyond. Approached by a circular drive framed by mature specimen plantings and meticulously landscaped grounds, the residence immediately impresses with its timeless Nantucket-inspired architecture and commanding waterfront presence. Encompassing approximately 5,100 square feet, the home offers 4 bedrooms and 3.5 baths thoughtfully designed to maximize light, space, and breathtaking water vistas from nearly every room. A grand two-story foyer welcomes you with a dramatic sightline through the home to the open bay beyond. Soaring ceilings, expansive living spaces, and walls of windows create an atmosphere of elegance and tranquility. The open-concept main level features a gracious living room with a wood-burning fireplace, a waterfront sitting room with a gas fireplace, and an office alcove. The expansive chef's kitchen is designed for both entertaining and daily living, featuring stainless steel appliances, granite countertops, and captivating views of the bay and heated waterside pool. Casual dining overlooks the water, while the formal dining room enjoys picturesque views of the protected boat basin. The first floor also includes a bayside en-suite primary bedroom, laundry room, and powder room. Upstairs, the luxurious primary suite and private sitting room offer unrivaled views over the boat basin and open bay. Two additional oversized guest bedrooms, each with water views, share a full bath, while the open landing provides yet another spectacular vantage point. Additional amenities include an elevator to all three level, whole house generator, spacious walkout basement ready for customization, 2-car garage and a heated waterfront pool. Rarely does a property combine such privacy, waterfront frontage, boating access, and panoramic views in one extraordinary setting. This is a once-in-a-generation opportunity to own a signature North Fork estate with dock and waterside pool. A truly exceptional waterfront retreat unlike any other.

This is a one of a kind fully reimagined, architectural masterpiece on Shelter Island, NY, boasting a flawless 2022 full-gut contemporary renovation by a serial tastemaker with an elite portfolio spanning NYC, California, and Hawaii. Located in the coveted Shorewood area, this premier estate offers a lifestyle of pure perfection and absolute privacy. Passing through the gated driveway, you instantly realize you are about to have an elevated experience. Indoor-outdoor living reveals breathtaking views at every turn, where the vast southwestern sky offers beautiful sunsets and truly magical light. Multiple designated spots allow you to dine alfresco while taking in the landscape. The interior spaces flow onto enchanted gardens, lawns, a private sandy beach, and a spectacular waterside pool, crowned by a roof deck with jaw-dropping panoramic views-leaving one to ask, why would you ever leave? Yet, when you do, a dinner excursion to Sag Harbor is entirely effortless, whether you choose to take a quick drive to the South Ferry or launch a boat trip straight off your own private dock.

Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home.

Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your dream legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the relaxed waterfront lifestyle. Designed for both entertaining and everyday enjoyment, the property features two private docks ideal for boating, paddleboarding, and kayaking, along with a spacious waterside deck overlooking the sparkling water. The first floor has a large waterfront room that opens directly onto the deck, complemented by 4 generously sized bedrooms and 4 full bathrooms. Upstairs, soaring cathedral ceilings frame an open-concept great room encompassing the living, dining, and kitchen areas. Walls of glass capture stunning panoramic water views, creating a light-filled and inviting gathering space. Privately situated off the great room, the expansive primary suite offers a large walk-in closet and a spa-inspired bathroom. Completing the property is a detached 2-car garage with a finished upper level, providing the perfect space for recreation, a home office, artist’s studio, or additional guest accommodations. A rare opportunity to enjoy waterfront living with private docks, beach access, tennis, and some of Shelter Island’s most captivating water views.

.38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary work has been done with the DOH, Planning Board, or building dept at this time. Please don't walk property without your agent present.

Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery.

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don't miss this opportunity to own a piece of paradise in Mashomack Preserve.

An extraordinary offering on the Peconic Bay, this refined Cedar Beach waterfront estate presents over 200 feet of direct, sun drenched, south facing shoreline and beach with a protected, private dock deep enough for a mid twenty ft boat, a truly rare combination of attributes to find on the North Fork. Thoughtfully designed to embrace its breathtaking setting, the house is set on a double lot whose southern exposure also produces the luxuries of southerly breezes and a true, useable and enjoyable beach not encumbered by prolific rocks or muck. The home itself is defined by soaring cathedral ceilings, sun-drenched interiors, and elegant entertaining spaces that seamlessly transition to expansive waterside terraces overlooking endless bay views and spectacular sunsets. Private ensuite accommodations and beautifully curated living spaces evoke a sense of understated coastal sophistication. Complementing the property, a separate waterfront parcel directly across the street features a newly refurbished private dock with direct bay access, offering an exceptional opportunity for boating, fishing, quick trips to Shelter Island, Sag Harbor, the Hamptons and other beautiful East End destinations. A exceptional and rare North Fork lifestyle centered around the beach, sun and water.

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.