luxury houses for sale Southold, United States

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.

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.

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.

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.

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

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 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. 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.

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.

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.

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.

Just 150 feet from a private association bay beach, and completely reimagined and renovated in 2018! This pristine ranch offers the ease of single-level living, the luxury of modern updates, and the warmth of timeless charm—all paired with an exceptional beachside lifestyle. The home was renovated in 2018 and features a beautifully updated kitchen and bathrooms, refinished wood floors, new carpeting in the bedrooms, new mechanicals, including a propane gas boiler, central air conditioning, insulation, a generator, and some new windows. This stylish 3-bedroom, 2-bath residence includes a spacious primary suite with an ensuite bath and walk-in closet. The tastefully designed kitchen showcases high-end cabinetry, quartz countertops, and bar seating for four, with an open-concept layout that flows seamlessly into the dining and living areas. The inviting living room retains its original craftsmanship and character, highlighted by a cozy propane fireplace, while thoughtful upgrades throughout provide comfort and efficiency. A bright home office with abundant natural light offers flexibility as a multipurpose space. One of the home’s standout features is the oversized 290 sq ft screened-in porch—perfect for relaxing after a day at the beach, entertaining guests, or unlocking additional potential. Enjoy outdoor living with a beautiful backyard yard, featuring a patio installed in 2018, and charming gardens. A full basement provides ample storage, and a rental permit adds excellent investment potential. Partial furnishings potentially available to be negotiated into deal or sold separately. Located just 150 feet from the entrance to the private bay beach, this home is the ideal summer getaway or fabulous year-round retreat.

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.

Dating back to the original 1871 layout of the Shelter Island Grove and Camp Meeting Association, Spring Garden Avenue is celebrated for its organic, rolling streetscapes and preserved 19th-century architecture. 5 Spring Garden Avenue is an authentic 1880 Victorian residence that embodies the classic style of the era, from its steeply pitched rooflines to its expansive exterior woodwork. The interior layout is expansive and true to its vintage, characterized by distinctive octagonal rooms on both the first and second floors. With five bedrooms, a sprawling third-floor attic loft, and a substantial footprint of covered decks and porches, the home offers a generous canvas within a historic setting. A significant structural update was completed in 2008, replacing the older foundation with a new poured concrete basement and structural footings, alongside the installation of a new roof. Featuring full access to the Shelter Island Heights Association tennis courts and beach club, this property represents an authentic piece of island history.

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.

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.

Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes from the South Fork. An amply equipped open kitchen pours out into the windowed dining area, with a fully screened in, covered porch just adjacent. The formal living room, complete with fireplace is spacious yet inviting. The en suite first floor primary is bright and beautiful. Upstairs are three more bedrooms and two baths, plus an open landing area, perfect for a study, at the top of the stairs. Add the two car garage and this home is a perfect fit for the Shelter Island lifestyle.

Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes from the South Fork. An amply equipped open kitchen pours out into the windowed dining area, with a fully screened in, covered porch just adjacent. The formal living room, complete with fireplace is spacious yet inviting. The en suite first floor primary is bright and beautiful. Upstairs are three more bedrooms and two baths, plus an open landing area, perfect for a study, at the top of the stairs. Add the two car garage and this home is a perfect fit for the Shelter Island lifestyle.

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.nStep 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 homes heritage. The adjacent dining and living spaces offer an inviting atmosphere, with natural light and tasteful detailing enhancing every moment.nFive 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.nOutdoors, 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.nAdditional amenities include a state-of-the-art HVAC system, smart home features, and ample storage throughout. The propertys layout and orientation maximize natural light, cross-ventilation, and the surrounding scenic vistas.nLocated moments from beaches, Mashomack Preserve, South Ferry, marinas, and local restaurants, this home captures the essence of Shelter Island livingquiet, 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 Islands most sophisticated and lifestyle-driven offerings, where every detail has been curated for comfort, elegance, and timeless appeal.