luxury real estate for sale Shelter Island Heights, United States

Discover a rare and compelling offering on Shelter Island where historic character and modern sophistication exist in perfect harmony. 7 Stearns Point Road presents a unique opportunity to live expansively-either as a private family compound or as an owner-occupied five-bedroom Bed & Breakfast. Originally dating to 1902 and thoughtfully reimagined for today's standards, the residence is set on 0.70 acres in the heart of Shelter Island Heights, just moments from Crescent Beach and Sunset Beach. Spanning approximately 5,838 square feet, with an additional 2,588-square-foot full-height basement, the home seamlessly blends timeless architectural details with contemporary comfort. Arranged across two distinct structures connected by a covered breezeway, the property's nine bedrooms and nine bathrooms are thoughtfully distributed between the original Annex-offering seven bedrooms-and a recently completed extension featuring two additional ensuite bedrooms. The new wing is further distinguished by a dramatic double-height living area and a dedicated wellness room, equally suited for private residential use or boutique hospitality. Generous entertaining spaces include two living rooms and a well-equipped kitchen designed to accommodate both intimate gatherings and larger-scale hosting. Outdoors, the grounds evoke a private resort atmosphere, featuring a heated 40' x 18' gunite pool, mature landscaping, and multiple areas for relaxation and entertaining. Two separate driveways provide added convenience and privacy for owners and guests alike. With zoning and approvals allowing for an owner-occupied five-bedroom Bed & Breakfast, along with the benefit of an existing liquor license for guest use, the property offers a rare level of versatility. Whether envisioned as a legacy family retreat, a refined island escape, or a boutique hospitality venture, the possibilities are both flexible and compelling.

A thoughtfully designed retreat offering peace, privacy, and understated luxury. Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants. The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a striking silhouette against the natural canopy. That hammock strung between two trees? Exactly where you'll spend Sunday mornings with coffee and a good read. Inside, the design philosophy is clear: let the outside take the stage. White walls, black accents, and a massive window wall make the front yard feel like your living room's best feature. The newly installed Ortal 110 TS fireplace anchors the open space, a sculptural centerpiece that warms the kitchen, dining, and living areas. Ascoli smart lighting throughout means you can set the color temperature to exactly your liking and automate it to match the rhythms of your day. The kitchen features Robern cabinets, a Thermador gas range, a double oven, and a refrigerator, plus a generous island for preparing all that local fish and farmstand produce. Upstairs, three bedrooms include a primary with an ensuite walk-in shower, a second bedroom with queen-sized built-in bunk beds and clever storage nooks, and a third with expansive windows overlooking the rolling front lawn. A second full bathroom with a tub serves the floor. Downstairs, heated floors make winter mornings civilized. The spacious bathroom features Robern cabinets and heated towel rack, while walk-in closets are generous enough that you and your partner won't need to negotiate territory treaties. Every detail considered, nothing overdone. The fully fenced backyard is its own retreat. Your dog thinks it's paradise. Your green thumb agrees. The newly built backyard office/art studio/yoga sanctuary, properly insulated with new windows and doors, offers a legitimate reason to work from home that doesn't involve your kitchen table. Whether it becomes your creative sanctuary, your focus zone, or just where you hide from houseguests, it's ready. The house comes with complete pool plans designed by Glenn Lawton at Spatial Arts. Modern amenities where they matter: EV charger, bike and board storage, without sacrificing the serenity that brought you to Shelter Island in the first place. Even the entrance makes a statement with its sculptural fountain and thoughtfully designed wood and bluestone steps.

Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

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.

Offered for the first time in decades - A rare slice of Long Island history. Step back in time without sacrificing modern comfort in this c.1600s Dutch Colonial farmhouse, gracefully set on .39 acres in the heart of the North Fork. With 4-5 bedrooms, 3 full baths, and over 400 years of character, this one-of-a-kind home blends heritage and warmth with beachy, coastal charm. Features include: * Original wide-plank wood floors? * Five wood-burning fireplaces for cozy evenings? * Charming eat-in country kitchen? * Spacious dining room & inviting living room? * Walk-in pantry + oversized laundry room with antique tub, washer/dryer? * Central air (1st floor) with retrofitting for additional areas? * Deeded beach access just steps away? Enjoy the best of both worlds-secluded and serene, yet very close distance to historic Greenport Village, home to the iconic carousel, North Fork Arts Center at the Greenport Theatre, and artisan shops. Explore the nearby charm of Historic Southold Town, and spend weekends sampling world-class restaurants, seafood markets, vineyards, craft breweries, and farmstands. Live music, local culture, and a quick ferry ride to Shelter Island make this the perfect year-round residence or getaway. Your North Fork dream awaits-steeped in history, surrounded by beauty.

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.

Set in the heart of the historic district, this c.1890 Greenport Village gem boasts 3 bedrooms, 2.5 baths plus a detached studio apartment. It merges many distinctive original details with thoughtful modern updates. A beautifully planted enclosed rear garden with deck and patio, perfect for relaxing and entertaining, leads to a renovated barn which features a 2-car garage and the spacious studio apartment. The main residence's generous ground floor living spaces include a front parlor and living room with original pocket doors, dining room, powder room, and a large renovated kitchen centered on a 48' Capital gas range. Upstairs there are three bedrooms and two full bathrooms, including one en suite. Refinished original wood floors add warmth and character throughout. The restaurants, shops and waterfront of the maritime village are just a few blocks away from this refined and peaceful retreat. ID922412

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.

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

Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the kitchen-perfect for relaxing or entertaining. There's plenty of potential here to update or expand with your own design vision. The property also includes a separate, partially completed renovated 1-bedroom cottage, complete with a legal kitchen, spacious bathroom, and inviting living area-ideal for guests, extended family, or as a rental income opportunity. A detached 2-car garage and ample outdoor space, including room for a pool, complete this rare offering in one of the area's most desirable locations. Owned solar panels provide significant energy savings with little to no ongoing cost. Don't miss your chance to enjoy the peaceful living just minutes from local favorites and the charm of the surrounding community. The sauna, lap pool in the basement are not being represented. This home is being sold As Is.

Discover this rarely available Pheasant Run Condo in Greenport. This desirable 2-bedroom, 2-bath, single-level condo features a bright eat in kitchen, a spacious living room with sliders opening to a private deck, and a full basement offering abundant storage. Features include a primary bedroom with an en suite bath, in addition to a comfortable guest bedroom and full guest bath. Ideally situated just steps from the community Clubhouse and pool, the condo also offers easy access to Greenport Village, beautiful beaches, local vineyards, and convenient transportation options. With low taxes and affordable monthly maintenance, this is an exceptional opportunity to own in one of Greenport’s most sought after condo communities.

Nestled on a serene .58-acre parcel just minutes from Wades Beach and Fresh Pond, this well-maintained ranch-style home offers the perfect blend of classic Shelter Island charm and modern convenience. Built in 1967 and lovingly cared for, the home features 1,340 square feet of single-level living with 3 bedrooms and 2 full baths, including a primary en-suite for added comfort and privacy. The light-filled interior boasts a thoughtful layout, complemented by a hall bath tastefully renovated in 2021. The property also includes a full basement, partially finished, offering flexible space for storage, recreation, or hobbies. Energy-conscious buyers will appreciate the owned solar panels, reducing utility costs and enhancing sustainability. In the expansive backyard, you'll find a versatile barn built in 2006, complete with a wood shop on the first floor and a spacious second-floor storage area. While the barn is equipped with propane heat, there is no running water. Whether you're looking for a full-time home, a weekend getaway, or a place with space to create, this Shelter Island spot has it all-great location, charm, and room to make it your own, just minutes from the beach and peaceful island surroundings.

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

Welcome to 619 Bailey Avenue, a fully restored and move-in ready farmhouse located on the fringe of Greenport Village. Originally part of a larger North Fork farm and estate, this incredibly well appointed circa 1900 residence has been thoughtfully re-imagined to blend modern conveniences with preserved period details. Original features such as hardwood floors, detailed millwork/moldings, and classic architectural elements have been carefully maintained, while updates throughout provide comfort and functionality. The custom kitchen is a standout, featuring a 48 range, oversized center island, custom cabinetry, and an 8-foot bi-fold glass door that opens to the rear yard, creating seamless indoor-outdoor living. The first floor offers a well-balanced layout with a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, the second level includes two guest bedrooms and a full hallway bath, along with a primary suite featuring vaulted ceilings, a large walk-in closet, and an en-suite bathroom with double vanity and a walk-in shower with a dual shower head system. The rear yard is expansive and private, complemented by a detached one-car garage. Not to mention, there is also an active permit in place for a 16' x 32' in-ground pool, a perfect opportunity to take this rare offering one step further. Conveniently located near Greenport Village's business district, Kontokosta Vineyard, Bay/Sound Beaches and Sep's Farm-stand, this amazing offering is sure not to last!

Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical sunsets. Wide waterfront vistas unfold across beautiful landscaping by Marders, broad greens lined with mature specimen plantings, and dotted with exceptional outdoor spaces from the patio to the breezy south lawn to the idyllic screened porch. From a circular peastone drive, past osmanthus, a mixed hedge, and hydrangeas, enter this sympathetically restored and exceptionally modernized farmhouse, by notable architect Kitty McCoy, through an adorable mud room vestibule. The gourmet kitchen has a breakfast area and French doors to the stone patio, perfect for lounging or waterside dining al fresco. The gorgeous dining room, adorned with restored original trim has a built-in cabinet for china and serveware. A bright and spacious living room with two sitting areas, fireplace, and dreamy bay window banquette seat leads to quite an enchanting wraparound screened porch, surrounded by water views. In a show of exceptional style by Culpepper Interiors, Holly Hunt window and Philip Jeffries wall coverings complement fixtures from Ralph Lauren, RH, and antique sourcing. A full bath and outdoor shower complete the main level. Upstairs, four well appointed bedrooms and two luxuriously updated baths, with Waterworks fixtures, are steeped in charm and benefit from delightful water views. With everything to love about the property and the home, the final question of the potential pool remains and a thorough examination of the site by EN-Consultants proposes two pool locations, including a south-facing waterside pool that conforms to zoning set backs and requires no variance, (to be independently verified by buyer's due diligence). Unique opportunity to own a turnkey, beautifully renovated farmhouse on the water with 400 feet of frontage, dock, sweeping views, and a gentle breeze.

This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage. The home currently has tenants, who will be leaving.

Stunning Greenport New Construction Colonial w/ Heated In-ground pool! Step into a seamless blend of turn-of-the-century elegance and contemporary comfort in this exquisite new construction Colonial. Designed with classic architectural details and high-end finishes throughout, this 4-bedroom, 4.5-bathroom residence offers over 2,700 square feet of thoughtfully crafted living space and includes a 10x20 heated in-ground salt water pool. From the moment you arrive, the crushed stone driveway and detached 1-car garage set the tone for the timeless appeal of this home. Inside, you’ll find gleaming hardwood floors throughout, complemented by custom millwork that adds warmth and character to every room. The open floor plan is anchored by a spacious Great Room with a stately fireplace, creating a cozy yet sophisticated gathering space. The gourmet kitchen opens effortlessly to the dining and living areas, ideal for entertaining. The main-level primary suite is a serene retreat, featuring a spa-like en-suite bathroom and ample closet space. A charming laundry/mudroom with custom red brick flooring offers both function and style. Downstairs, the fully finished basement expands the living space with a second fireplace, a wet bar, a full bathroom, and a dedicated media room—perfect for movie nights or game-day entertaining. Enjoy outdoor living on the poolside private patio, ideal for morning coffee or summer barbecues. Every inch of this home reflects a perfect balance of traditional craftsmanship and modern convenience. A rare opportunity to own a new home with historic character in every detail that is in close proximity to Greenport Village, walk to 67 Steps Beach along the LI Sound and direct access to all that the North Fork has to offer!

A masterful blend of timeless character and elevated modern luxury, this designer-renovated Shelter Island residence delivers a curated living experience across more than an acre of lush, private grounds. Every space has been thoughtfully reimagined with bespoke finishes, high-end materials, and a refined aesthetic that feels both effortless and elegant. Step inside to sun-filled interiors with clean lines, wide-plank flooring, and a seamless flow ideal for year-round living and entertaining. The designer kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, and a sophisticated palette that complements the home's heritage. The adjacent dining and living spaces offer an inviting atmosphere, with natural light and tasteful detailing enhancing every moment. Five beautifully appointed bedrooms and three spa-inspired bathrooms provide comfort and privacy for guests or full-time residents. Each room reflects a balance of luxury and warmth, from serene color schemes to thoughtfully selected fixtures and finishes. A luxurious primary suite includes a spa-style bathroom and walk-in closet, creating a private retreat within the home. Outdoors, resort-style living comes to life. A heated gunite pool, expansive bluestone patio, and multiple lounging and dining areas create a truly elevated summer retreat. Manicured gardens, mature landscaping, and a serene pond offer tranquil views and exceptional privacy, while the acre+ setting provides ample space for recreation, entertaining, or simply enjoying the natural beauty of Shelter Island. The property also includes an outdoor kitchen, fire pit, and multiple shaded seating areas, perfect for alfresco dining and gatherings. Additional amenities include a state-of-the-art HVAC system, smart home features, and ample storage throughout. The property's layout and orientation maximize natural light, cross-ventilation, and the surrounding scenic vistas. Located moments from beaches, Mashomack Preserve, South Ferry, marinas, and local restaurants, this home captures the essence of Shelter Island living-quiet, refined, and effortlessly connected to the best of the East End. Move-in ready and finished to a designer standard, this is a rare opportunity to own one of Shelter Island's most sophisticated and lifestyle-driven offerings, where every detail has been curated for comfort, elegance, and timeless appeal.

Perched atop the bluffs of the Long Island Sound, this carefully designed showstopper is located within the desirable Eastern Stirling Shores community, offering private beach access just a short walk away. The rear yard provides a true resort-style setting, where you can bask in full sun poolside beside the natural gas–heated, in-ground saltwater pool with electric cover, all while enjoying exceptional privacy created by mature privet hedges surrounding the property. Inside, the home features beautiful white oak floors throughout and a stunning chef’s kitchen anchored by a dramatic waterfall stone island. The main level offers one of two primary en-suite bedrooms complete with dual walk-in closets, along with a full-size laundry room with sink, pantry, half bath, and multiple living spaces centered around a gas fireplace. The second floor features a second primary en-suite bedroom with a spacious walk-in closet, private bathroom, and a balcony capturing water views of the Long Island Sound. This level also includes an additional stacked laundry area and three more en-suite bedrooms, each with its own private bathroom and balcony access. Completing the home is a large attached two-car garage that flows seamlessly into the main living area, as well as a third garage located beneath the main level. A spacious walk-out basement with high ceilings offers the opportunity to easily finish over 1,000 additional square feet of living space. Offering an exceptional blend of location, amenities, and turnkey condition, this impressive home delivers the very best of North Fork coastal living.

Wonderful remodeled home located in secluded Silver Beach on West Neck Bay. With water on 2 sides of this lovely estate, enjoy the water views from all rooms. 5 Bedrooms, 6 baths, finished lower level and open rooms, this is a wonderful home to enjoy for the summer or year round. The large open kitchen with high-end appliances opens to a massive dining room overlooking the rolling yard down to the water. The primary bedroom on the second floor features a full bath and two very large walk in closets and French doors out the a balcony. Just off the primary bedroom is one of two laundry areas and 2 guest suites all en-suite. On the main level is an en-suite guest bedroom, library with fireplace, open kitchen and dining room, another full bath for the pool area and a living room with an additional laundry just off the service entrance. This lovely home features a veranda with a pool, detached garage, partially finished lower level and an expansive yard and deep water dock. A wonderful home with exquisite views and room for everyone.

A Cinematic Waterfront Estate on Shelter Island, designed by acclaimed architect James Merrell. At the meeting point of sky and sea, this extraordinary contemporary waterfront retreat redefines island living. Designed to embrace panoramic views of Coecles Harbor and Gardiners Bay, the residence offers serenity, sophistication, and seamless indoor-outdoor connection - a rare combination on Shelter Island's coveted Little Ram peninsula. A discreet approach reveals a masterpiece with walls of glass, natural stone, and warm wood tones. Inside, expansive open living spaces capture the light and horizon from every angle. The main level flows effortlessly from the grand living area and gourmet kitchen to multiple terraces overlooking the water - perfect for entertaining or quiet reflection. 8 bedrooms, including a dramatic primary suite, ensure space and privacy for family and guests. Outdoors, a resort-like environment features a heated waterside pool, lush lawns, and a deep water dock for boating adventures across the Peconic and beyond. With its sophisticated architecture, cinematic setting, and direct access to the best of the Hamptons and Shelter Island, 8 Little Ram Island Drive offers a lifestyle that feels both secluded and world-class.