luxury houses with pool for sale Shelter Island, United States

Discover the epitome of modern elegance and serene coastal living in this stunning contemporary nestled in a quiet and secluded area with private beach access. The home exudes grace with sleek lines, a harmonious blend of stone and glass, and floor-to-ceiling windows that bathe the interior in natural light and frame the breathtaking surroundings. An artistic vibe with an open floor plan that seamlessly connects the living, dining, and kitchen areas, create an expansive and inviting space ideal for entertaining and relaxing. The primary suite is a haven of tranquility and features a private balcony overlooking the lush grounds and a picturesque view of Gardiner's Bay, a luxurious en-suite bathroom with a soaking tub, chic and spacious office space, and generous walk-in closets. The other three bedrooms are thoughtfully designed, each offering its unique style and comfort, ensuring every guest finds their perfect space. Outside, the exquisite swimming pool awaits, offering a refreshing escape on warm summer days, and the lavish hot tub provides a perfect spot to unwind under a starlit sky. The home is fully equipped with a chef's kitchen, outdoor barbeque, a sumptuous mahogany outdoor shower, and a Tesla charger. Situated within a coveted private beach community, this elegant home offers direct access to the pristine shores of Gardiner's Bay; perfect for the nature lover and water sport enthusiast. Make this spectacular home yours and Indulge in the luxury, serenity, and beauty of this magnificent coastal retreat.

Stunning Resort-Style Home with Modern Smart Features on the North Fork Discover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by tranquil Islands End public golf course, the popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. This neighborhood beach/park offers paddleboard and kayak stations along the marina, this home is perfect for embracing the North Fork's outdoor lifestyle. As a state-of-the-art smart home, it provides remote access for lighting, heating, and air conditioning, music indoors and outdoors, and televisions strategically placed on the second floor, in the main living areas, and in a private TV room in the basement. The expansive floor plan offers not one, but two luxurious owner's suites, one on the main level and another on the second floor, complemented by two additional bedrooms with private bathrooms. With a sleek, modern aesthetic, the home is thoughtfully designed for indoor-outdoor living. Outside, an elegant pool with a waterfall and evening lighting package becomes the centerpiece of the outdoor experience, complete with an option for an outdoor kitchen. Stunning dining area, and a lounge with a fireplace-perfect for entertaining or relaxing in style. This property brings the quality of its design and build to the forefront across all three levels, offering a flawless blend of comfort, functionality, and contemporary elegance. Indulge in this rare opportunity to own a slice of resort-like paradise on the North Fork.

Located on 1.4+/- acres of park-like grounds, this three bedroom, two bath residence, owned and meticulously maintained by an award-winning architect and his wife for the past twenty years, offers a serene setting to relax and entertain. The focal point of the home is its spectacular great room with a 20' ceiling, wood burning fireplace, dining space and chef's kitchen. Three sliding glass doors lead from the great room to an expansive 2,500+/- sq. ft. deck featuring a heated pool, BBQ area, dining table, and multiple seating areas. Completing the first floor are a bedroom with direct access to the pool area, a bedroom currently set up as a den, and a full bath. The second-floor primary bedroom is a private retreat, offering a spacious bath with double sinks, walk-in shower and soaking tub, a generous walk-in closet, and a 500+/- sq. ft. private deck with views of the expansive lawn and a spiral staircase down to the pool deck. With a carport for one car and easy access to East Hampton Village shops and ocean beaches, this home offers the best of Hamptons living.

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a to be built opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

New construction coming to Bay Point by Konner Development! The proposed 4 bedroom, 4.5 bathroom home will include a gourmet chef's kitchen, a heated inground gunite pool, and a deepwater dock. With beautiful views of Sag Harbor Village downtown harbor, as well as the uptown cove, you do not want to miss out on this incredible opportunity!

Newly complete in the historic district, this reimagined 6-bedroom, 5 bath home is a rare find. Renovated and expanded by the developer, this historic cottage now boasts a footprint with over 3,800 +/- sq.ft of living space. A breezeway connects the cottage to a new house, offering 2000 +/- of new construction. Set on a substantial .35-acre lot, the backyard features a new gunite pool, pool shed, and patio that is perfect for outdoor dining and entertaining. Inside offers tremendous versatility. Each wing has 3 Bedrooms, their own kitchen, dining and living areas. The addition has an open floorplan and crisp white interiors. A double-height great room opens to the kitchen and dining area that overlook the backyard and patio. Upstairs there is an ensuite primary and balcony overlooking the backyard, as well as 2 guest bedrooms with an adjoining bathroom. Laundry is conveniently located on each floor. The location offers a fantastic lifestyle, 0.7 Miles to Main Street, with a couple dozen high-end restaurants and bars, boutique shops, and renowned Bay Street Theater and Sag Harbor Cinema. The homes upgraded amenities include Central A/C and Central Vac.

Perched on higher ground, in a quaint, peaceful setting, this charming beach house captures the beauty of its surroundings, with sweeping views of Three Mile Harbor. Sunlight pours through the home all day, creating a warm and inviting atmosphere. Designed with comfort and space in mind, this 3-bedroom home offers the perfect balance of areas for entertaining and quiet moments of solitude. The open living spaces flow seamlessly, while each bedroom provides a private retreat, including balconies off the primary and guest room. The outdoor spaces are equally as enchanting, with peaceful deck areas ideal for dining or relaxing, and a sparkling pool and spa surrounded by lush greenery and flowering plants. The main floor features a spacious suite, while the second floor offers a generously-sized primary bedroom. An added bonus is the lower level, offering additional space to gather, work, or find some quiet time. Meticulously maintained inside and out, this home exudes warmth, elegance, and tranquility-a true haven in a breathtaking location.

Looking for one-level living? This incredibly well-maintained and immaculate three-bedroom, two-and-a-half-bath home is located on 0.86± acre. Two paper roads on either side make the property feel much larger. Situated on a lush and gorgeous cul-de-sac in the Northwest Woods, this home is only 4 miles from East Hampton Village and 2.4 miles from a beautiful bay beach perfect for kayaking or paddleboarding. The open floor plan with a center fireplace and soaring ceilings offers a large primary bedroom on one end and two large guest rooms on the other. An attached 1.5-car epoxy floor garage and a huge basement with 8-foot ceilings offer many future possibilities. The generous two-tiered decking with a retractable awning overlooks a large pool and has a conveniently located outdoor shower.

Perched on a hill at the end of a cul de sac, this celebrity's own classic East Hampton retreat has abundant peace and beauty. With five bedrooms, multiple indoor and outdoor gathering spaces in which to enjoy the seasons, two wood-burning fireplaces, a Gunite pool, beautiful mature landscaping, and a two-car garage, this house has everything you need to enjoy sunsplashed or cozy happy times in the Hamptons.

Imagine waking up to the serene sounds of gentle waves and the breathtaking beauty of the sunrise over the bay. Welcome to 38 Bay Avenue in Sag Harbor, NY—a rare gem set on 2.29 acres of pristine land with 450 feet of bay frontage. This property is not just a plot of land; it's a canvas for creating your dream coastal retreat.Designed by the renowned architect Ryan T Kesner, the approved plans for this estate envision a luxurious 5-bedroom, 7-bathroom home sprawling over 5,266 square feet of meticulously designed interior living space, complemented by over 10,000 square feet of stunning exterior space. Imagine entertaining guests in the expansive living area on the first floor, which boasts 2,976 square feet of open-plan living space with soaring 10-foot ceilings, flowing seamlessly onto 1,641 square feet of decks and porches. Picture warm summer days by the 705-square-foot pool, perfectly situated for both relaxation and recreation.The second floor continues the theme of spacious elegance with 2,290 square feet of living space and an additional 953 square feet of outdoor decks, providing ample room for family and guests to enjoy the panoramic bay views. And for those who seek a truly unparalleled perspective, the 360-degree roof deck offers 2,555 square feet of outdoor living space, where the vistas of Sag Harbor are yours to enjoy from sunrise to sunset.But the allure doesn't stop there. The basement level, while not included in the primary living space calculations, adds an impressive 3,500+ square feet of additional space. This includes a 636-square-foot two-car garage, a 270-square-foot lower lobby and elevator room, a 184-square-foot outdoor lobby, and a 588-square-foot bayside recreational area. With three storage areas totaling over 2,300 square feet, you'll have all the room you need for kayaks, paddleboards, and other outdoor equipment. Plus, a 455-square-foot bayside patio area invites you to create unforgettable memories by the water's edge.Every detail of this home has been carefully considered to meet AE 6 flood zone building codes, ensuring not only luxury but also safety and durability. 38 Bay Avenue is more than a property; it’s an opportunity to craft a lifestyle of elegance, tranquility, and connection to nature. Come, build your dream on the bay, and let the story of this exquisite home unfold with your unique vision.

This stylish, sun filled, completely refurbished 60s beach bungalow is located a stone's throw from Circle Beach. Meticulously restored from soup to nuts, including a 14x28 heated gunite pool and upgraded septic. No need to deal with local permitting or contractors. Located a few blocks from beach and 3.5 miles to downtown Sag Harbor. With a surfer inspired decor there are three bedrooms and one bathroom. Rounded out with a chef's kitchen and a tastefully designed back yard oasis you may never to want to leave except maybe stroll to Circle beach at the end of each day to experience the best sunset in the Hamptons. This home has all the bells and whistles and is no 5,000 square foot Hampton's McMansion but a pristine, chic seaside bungalow in a trendy up and coming beach neighborhood with tons of built in cabinetry and closets. The perfect starter home in the sought after Pine Neck community. Sag Harbor Schools

Tucked away on a quiet street in Springs, is this lovely traditional. Drive to up the winding gated driveway and enter a gracious living space with 4 bedrooms, 4 full and 2 half baths, large eat-in kitchen, living room with cathedral ceiling, separate dining room with second living room. Second floor master is separated from other guest bedrooms. All bedrooms have bathrooms ensuite. Finished basement and media area. Outdoor bluestone patio with teak furniture and outdoor dining table, and a freeform heated pool completes a private rear yard. Wonderful place to spend your spring, summer, winter and fall! [[Rental Registration # 24-77]]

Located within East Hampton's Clearwater Beach Association this 2725 square foot home truly has it all, including private beach and marina rights. The main, open concept, level offers two great rooms with 10 foot ceilings and a masonry fireplace, a spacious windowed dining area, full bath and an open gourmet kitchen with sliding glass doors showcasing the beautifully landscaped yard and pool. The heated saltwater pool is surrounded by a professionally landscaped backyard with lush and mature native beach grasses and trees and fire pit area. On the second level you can find the primary bedroom with an ensuite full bath and walk in closet. Three additional bedrooms and another full marbled bath are also located on the second level. Each bedroom has recently had California Closets installed. A detached two car garage was added on in 2021.

This exciting four-seasons contemporary sits on five secluded acres, with room for tennis, exactly midway between East Hampton and Sag Harbor off Route 114 (Where it seems everyone wants to be.) The twenty-foot-ceilinged Great Room is the light-filled centerpiece of a home and property that has been packed with every imaginable amenity ....... a virtual cornucopia of Hamptons Lifestyle. The open kitchen (with 8-burner Viking Range, 2 wine fridges, (plus, plus, plus!) assures that even the most focused chef has everything they need, yet are still in the center of it all, with direct line-of-sight to the hearth and big screen. The 500 square-foot primary suite is resolutely private as the only bedroom on the second floor. (The luxurious radiant-floored bath, private sitting-room/study, fireplace, and room for two distinct sitting areas conspire to redefine luxury, while providing needed respite.) The lower level has been developed with a media center, and dramatic wine wall, with room for exercise equipment, pool table and more. The outside is divided into Two Distinct Areas: The first is an unparalleled bluestone courtyard featuring a 20' x 50' gunite pool with automatic cover, a massive stone outdoor kitchen, a bocci court, and a personal herb/vegetable garden. The second comprises of a rolling lawn leading down to a cinematic circular outdoor salon with beckoning fire pit. Bridging the two distinct adventures is a dramatic entertaining center with an arbored outdoor dining room, and a conversation center with fire pit. All this leads into the house thru the perfectly located and ridiculously-comfy screened porch. A first floor junior primary, two other guest rooms and small study complete this movie-set story. Merchants Path is less than three miles to the Wharf in Sag Harbor or Main Street East Hampton, right off Route 114. 122 Merchants Path has it all. Exclusively ours!

Discover your dream retreat in this distinctive contemporary home, beautifully nestled on a private flag lot off Bull Path in East Hampton. Designed for modern living, the open concept kitchen and living room seamlessly blend functionality with style, featuring double height ceilings, sleek angles, ample natural light, and a warm wood-burning stove that invites cozy gatherings. This thoughtfully designed residence boasts four spacious bedrooms and four bathrooms (three of them en-suite), providing plenty of room for guests. A separate dining room offers an elegant space for entertaining, while the adjacent den serves as a versatile area for relaxation or work-from-home convenience. Step outside and the expansive deck invites you to soak up the sun, while the heated pool beckons for refreshing swims on warm summer days. An outdoor fireplace creates a beautiful ambiance for evening gatherings and the charming patio is ideal for al fresco dining. Multiple sitting areas offer space for entertaining, and a garage provides additional room for parking and storage. This secluded locale offers the dual advantage of privacy while remaining close to both Sag Harbor and East Hampton village restaurants, shops, transportation and beautiful ocean beaches.

Ideal location, large and beautiful home on an expansive property, offering privacy, an oversized pool, and tennis. This new exclusive has it all! Located on a quiet cul-de-sac, just 3 miles from Sag Harbor Village and 3.7 miles to East Hampton Village, lies this beautiful 4-bedroom, 5-bathroom home. Featuring an open floor plan, the home flows seamlessly from the natural light filled living room with 24' vaulted ceiling and gas fireplace overlooking the expansive back yard, to the eat in kitchen, dining area, separate media room with glass framed pocket doors, enabling privacy and separate space when desired, a full bathroom and an enclosed porch with dining and entertaining space. The first floor also hosts a large Junior Primary ensuite with shower and jacuzzi tub and its own private enclosed porch. The second floor offers two large ensuite guest bedrooms, the Primary ensuite bedroom with a large deck overlooking the property, an office/5th bedroom, and a separate bonus room. The lower level includes an additional 1,200± sqft. of finished living space and 450± sq.ft. of storage. The two main level enclosed porches total 420± sqft.of additional enjoyment bringing the total interior square footage over 3 levels to 6,070 ± sqft. which excludes the attached 2-car garage. Central to all, this home offers community tennis shared by 11 other homes, and lies 700 yards to the Northwest Woods hiking and biking trail, 4.7 miles to the ocean and EH Main Beach, 2 miles to the Sag Harbor Golf Course, 2.6 miles to Havens Bay Beach, and 3 miles to marinas, boat launches, and yacht clubs. This exceptional property offers you the convenience and benefit of living in close proximity to every activity, shopping, dining, and entertainment venue the Hamptons has to offer, while still affording you the privacy 1.5± acres grants. And as if that wasn't enough, the winter sunsets from the Primary Bedroom deck are extraordinary! Priced to market and a must see! Floor plans available upon request.

Situated on a tranquil private path, this sophisticated six-bedroom home offers luxurious living spaces and serves as a haven for outdoor enthusiasts. Surrounded by pristine woodland and located across from Trout Pond with its scenic hiking trails and excellent fishing spots, this residence is ideally positioned between Sag Harbor Village, Bridgehampton, and Southampton. A world-class marina is just a stone's throw away. Two renowned golf courses and a National Wildlife Preserve is less than a mile away. Spanning 7,000 square feet across three levels, the home provides ample space for both family living and entertaining. The open-plan gourmet kitchen flows into spacious living areas adorned with coffered ceilings and a cozy wood-burning fireplace. A formal dining room sits adjacent to the kitchen. The second floor consists of a primary suite and four ensuite guest rooms, along with convenient dual washer and dryer setups. The finished lower level features a music/media room and a sixth ensuite bedroom, as well as a seventh bedroom outfitted with six bunk beds. Outside, a lush and meticulously landscaped garden envelops the expansive gunite pool and spa, complemented by blue stone terraces. A bocce court and outdoor fire pit add to the backyard's entertainment options. This property presents an exceptional opportunity for year-round residency or enjoying an extended Hampton season. Don't miss out on this remarkable offering for those seeking refined living in a natural paradise.

Tucked away down a picturesque drive, lined with whispering pines, lies a stately home that is private and elegant. This 4,000-square-foot residence, situated on a private 2.16 acres, is a hidden gem in the heart of East Hampton. Surrounded by mature trees and lush landscaping, this home is a sanctuary of tranquility. Meticulous attention to detail has been given to bring the lush green grounds into the interior, with large windows and doors in all principal rooms offering outdoor views. Upon entering the first floor, you are welcomed by a two-story entryway and a striking open staircase leading to the second floor. The first floor also houses a large library with numerous built-ins, oversized windows, and an artist's studio. As you ascend to the second floor, you are greeted by abundant natural light that fills the home. The living room is spacious and open, boasting high ceilings of 14ft., a fireplace, and large windows and doors that lead to the outside and the upper-level inner courtyard. The residence features four spacious bedrooms and three baths, including a large primary bedroom with 12 ft. ceilings, a private deck, a bath, and two closets. The chef's kitchen and a large dining room, with doors leading to the outside and the inner courtyard, make this home perfect for entertaining. Off the living room, an outdoor deck leads to a heated gunite pool with a bluestone patio and a pool house with an outdoor shower. Additional features include a detached artist's studio with a patio, a tiered garden with irrigation, and a rippling man-made stream. The mechanicals have been recently updated, and a generator that runs the whole house ensures uninterrupted comfort. This property has been meticulously designed to bring the beauty of nature into the home and to inspire your inner artist. Located a short distance from the Village, this home is sure to appeal to many and is not expected to last. Experience the unique blend of privacy, elegance, and natural beauty that this East Hampton retreat offers.