luxury houses with pool for sale Shelter Island, United States

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor-outdoor lifestyle experience. The living room, dining area, and gourmet chef's kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range. Designed for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six person barrel sauna and cold plunge. Beautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Located in the premier Landfall community just 500 ft +/- from private resident-only beach access, this beautifully updated East Hampton contemporary offers a private retreat designed for effortless Hamptons living. Set on .92 +/- acres at the end of a long private drive, the 4-bedroom residence blends modern design with serene natural surroundings. Sun-filled interiors feature soaring ceilings, an open-concept living and dining area anchored by a wood-burning fireplace, and walls of glass sliders that seamlessly connect to expansive outdoor entertaining spaces. The gourmet kitchen is both refined and functional, complete with a substantial center island, Sub-Zero, Viking, and Bosch stainless steel appliances, and an ideal flow for gatherings large or small. The primary suite serves as its own peaceful escape with direct deck and pool access, while the finished lower level offers additional flexible living space including a media area, workspace, guest accommodations, and full bath. A second attached garage presents excellent potential for a gym, studio, or recreation space. Outdoors, the property is tailored for summer living with a 20' x 40' heated pool, expansive decking for lounging and dining, fire pit area, outdoor shower, zen walking garden, sprawling lawn framed by mature trees and natural landscaping, and a removable child safety fence for the pool. Additional highlights include an EV charger and a strong history of short-term summer rentals, offering excellent lifestyle and investment appeal. Just moments away, enjoy endless stretches of shoreline, calm bay waters, and unforgettable sunset skies.

Newly built modern estate on approximately 3.65 acres overlooking Fresh Pond and Sag Harbor Bay. Located in coveted North Haven, less than one mile from Sag Harbor Village, this 8,960± SF residence offers privacy, scale, and proximity to beaches, marinas, and dining. The home features 8 bedrooms and 8.5 bathrooms, with expansive glass walls, a double-height foyer, and open-concept living areas designed to maximize natural light and water views. The chef's kitchen includes Sub-Zero and Wolf appliances, marble countertops, an oversized island, and a full butler's pantry. Indoor-outdoor living is emphasized with multiple covered porches, terraces, and retractable glass doors. The main level includes a junior primary suite with spa-like bath and sitting room, along with additional living, dining, and service spaces. The upper level offers a water-view primary suite with dual walk-in closets and a luxury bath, plus five ensuite guest bedrooms and a secondary lounge with wet bar and terrace access. Outdoor amenities include a 20' x 50' heated gunite infinity-edge saltwater pool with spa, limestone patios, mahogany terraces, and a 320± SF pool house with kitchenette and firepit. The property also allows space for a future pickleball or padel court. A refined North Haven offering combining modern design, privacy, and convenient access to Sag Harbor Village.

Newly built cedar-shake estate on approximately 2.37 acres overlooking Fresh Pond and Sag Harbor Bay. in coveted North Haven. Offering 8,030± SF of living space, this traditional-style residence blends classic Hamptons architecture with modern scale, just minutes from Sag Harbor Village, marinas, beaches, and dining. The home features 7 bedrooms, 7 full and 2 half bathrooms, with wide-plank white oak floors, tray ceilings, and a wood-burning fireplace anchoring the main living spaces. Walls of sliding glass doors create seamless indoor-outdoor flow and enhance natural light throughout. An eat-in chef's kitchen with premium appliances serves as the heart of the home, complemented by a first-floor office/den. Multiple living and dining areas provide flexibility for everyday living and entertaining. Upstairs includes a beverage center, spacious bedroom suites, and two rear balconies with pond and bay outlooks. The layout is designed for comfort, scale, and easy living. Outdoor amenities include a 20' x 50' heated pool with bluestone patio, covered dining and lounge areas, and a fireplace-centered outdoor living room for year-round enjoyment. A rare highlight is the opportunity to add a 2,500± SF guest house, offering exceptional flexibility for future expansion. A refined North Haven offering with water views, privacy, and timeless design close to Sag Harbor Village.

22 Settlement Court, EH, recently completed and published, the house is featured in the newly released book INSIDE THE HAMPTONS. This custom contemporary on an ultra-private hilltop acre+ surrounded by reserve, moments to bay beach, with sunsets over Northwest Harbor. Flooded with light, featuring high ceilings and walls of windows overlooking gardens, a shaded dining deck, and a heated gunite saltwater pool. Enormous living room with a fireplace, white oak floors throughout, an open chef's kitchen with professional appliances and leathered quartz countertops, a den/library with a fireplace, a powder room, and a large ground-floor master wing plus guest suite-3357 sq. ft. of finished space. There is 2,557 sq ft on the lower level with 10-ft ceilings, including a guest suite with a walk-out garden and spa bath. The house can be greatly expanded. Luxury amenities include 3-zone central air, solar panels on the roof, a backup generator, a garage, and a raised vegetable garden. Just listed, first offering of this exceptional, serene oasis. Designer's own published custom contemporary on an ultra-private hilltop acre+ surrounded by reserve, moments to a deeded bay beach with sunsets over Northwest Harbor. Flooded with light, featuring high ceilings and walls of windows overlooking gardens, a shaded dining deck, and a heated gunite saltwater pool. Enormous living room with fireplace, white oak floors throughout, open chef's kitchen with professional appliances and leathered quartz countertops, den/library with fireplace, powder room, large ground-floor master wing plus guest suite. Full 2500 sq ft lower-level with 10 ft ceilings, including a guest suite with walk-out garden and spa bath. Luxury amenities include 3-zone central air, solar panels on the roof, back-up generator and a garage. First offering of this exceptional, serene oasis.

Huge potential. This turn of the 20th century gem was the residence of a single family through generations since its inception! A Queen Anne style house with its classic front gable and massive covered front porch invokes grandeur of times past as it sits prominently on prestigious Lumber Lane. Much of the original detail has been maintained including millwork, windows, doors, staircase, siding, structure, and the bones of this grand dame appear of high integrity. Collectors often favor a little patina over a flurry of modifications de jour. Such is the case with this roughly 2,100 sf residence, currently configured as two-family home, offering 4 bedrooms, 2 baths, 2 kitchens, 8’8” first floor and 8’4” second floor ceiling heights. In addition, the “1/2 story” attic with four dormers adorned with large leaded glass windows facing in each direction of the compass can stir one’s imagination of what it could become. 119 Lumber Ln located in the heart of Bridgehampton is a short distance from Main St, the LIRR station, numerous beaches, all other Hamptons hamlets, and provides over 5,000 sf of allowable lot coverage: ample space to accommodate expansion of the primary structure as well as various accessory structures and swimming pool/spa, or build a magnificent new home.

Phil Kouffman, one of The Hamptons' most revered builders is poised to break ground on these two striking homes, both well situated equidistance to Sag Harbor or East Hampton village. There is room for Pickle Ball on both properties. (#15 could have Tennis if a buyer prefers.) These homes are not just destined to be wonderful small estates, but at pre-construction pricing they are currently great values

Phil Kouffman, one of The Hamptons' most revered builders is poised to break ground on these two striking homes, both well situated equidistance to Sag Harbor or East Hampton village. There is room for Pickle Ball on both properties. (#15 could have Tennis if a buyer prefers.) These homes are not just destined to be wonderful small estates, but at pre-construction pricing they are currently great values

Sophistication and Style!! The only way to describe this outstanding home in the heart of the Near Northwest, moments to East Hampton Village! After undergoing an exciting transition, the home features the addition of a show stopping 378 sf (+/-) designer kitchen/lifestyle area, and 125 sf (+/-) of interior alterations including a beautifully designed great room featuring soaring vaulted ceilings, dramatic 2 story stone fireplace, a study with custom built library shelves, new bathrooms, and a beautifully finished lower level. The stunning landscaped grounds offer 1164 sf (+/-) of bluestone patio, entertainment deck with retractable awning, and reconfigured pool with 160 additional square feet. The whole interior has been professionally designed with top of the line finishes and high end style. This house must be seen to be appreciated!

Presenting a masterfully designed estate where pedigree and natural beauty converge. Published in Architectural Digest, with interiors by Heidi Caillier, this impeccably fashioned 5,300+ square foot home is set at the end of a white pebble driveway amid beautifully manicured grounds by Marders. A covered porch opens to a gracious foyer, introducing interiors that balance sophistication with exceptional craftsmanship. An additional adjoining lot with a letter of buildability can support a substantial home, pool, tennis, and garage, completing this four-acre compound ideally situated between East Hampton and Sag Harbor Villages and just moments from beautiful ocean beaches. The main level features a spacious living room with two French doors, a marble-mantel wood-burning fireplace, and an effortless sense of light and scale. The eat-in chef's kitchen by deVOL includes SubZero and Wolf appliances, a generous center island with seating, and a walk-in butler's pantry with two wine cellars. Kitchen wall tiles by BDDW, painted with offbeat flora-and-fauna vignettes reminiscent of Delft pottery, bring an artful note to the space. Throughout the home, a series of unexpected design moments catch the eye, including a pantry painted head-to-toe in carmine red. The dining room, with arched doorways, hand-painted walls and ceilings, and an abundance of windows and French doors, creates a striking setting. The library is wrapped in floor-to-ceiling bookshelves and provides a sophisticated, yet cozy retreat. The first-floor primary suite features French doors opening to a private patio, beamed ceilings, built-in closets, a glass-enclosed office, and an elegant bath with a pedestal tub and marble shower. Additional highlights on this level include a stone-tiled mudroom connecting to the two-car garage, a custom laundry room, and a full bath with custom tiles by Tabarka Studio and a marble sink from Drummonds. A spindle staircase leads to the second floor, which offers a second primary suite with beamed tray ceilings, six windows, and an en suite bath with an alcove soaking tub and custom vanity. Three additional en suite guest rooms and a landing area with built-in seating complete this level. The 2,200 sq. ft. lower level continues the home's sense of luxury with a large media room, dining area lined with bookshelves, kitchenette with stone counters, and a second laundry room. A sixth bedroom, seventh bathroom, gym, custom built-in seating, and a linear wet bar complete the space. The landscape, designed by Charlie Marder, surrounds the property in natural beauty with hundreds of trees, including 30-foot Lebanese cedars, Asian pines, and gingkos. A heated gunite pool and spa are bordered by crepe myrtles, boxwoods, wisteria, and stone fruit trees. The patio offers multiple areas for entertaining, while a hidden path leads to an outdoor shower and a separate outbuilding housing a large sauna.

Presenting a masterfully designed estate where pedigree and natural beauty converge. Published in Architectural Digest, with interiors by Heidi Caillier, this impeccably fashioned 5,300+ square foot home is set at the end of a white pebble driveway amid beautifully manicured grounds by Marders. A covered porch opens to a gracious foyer, introducing interiors that balance sophistication with exceptional craftsmanship. The main level features a spacious living room with two French doors, a marble-mantel wood-burning fireplace, and an effortless sense of light and scale. The eat-in chef's kitchen by deVOL includes SubZero and Wolf appliances, a generous center island with seating, and a walk-in butler's pantry with two wine cellars. Kitchen wall tiles by BDDW, painted with offbeat flora-and-fauna vignettes reminiscent of Delft pottery, bring an artful note to the space. Throughout the home, a series of unexpected design moments catch the eye, including a pantry painted head-to-toe in carmine red. The dining room, with arched doorways, hand-painted walls and ceilings, and an abundance of windows and French doors, creates a striking setting. The library is wrapped in floor-to-ceiling bookshelves and provides a sophisticated, yet cozy retreat. The first-floor primary suite features French doors opening to a private patio, beamed ceilings, built-in closets, a glass-enclosed office, and an elegant bath with a pedestal tub and marble shower. Additional highlights on this level include a stone-tiled mudroom connecting to the two-car garage, a custom laundry room, and a full bath with custom tiles by Tabarka Studio and a marble sink from Drummonds. A spindle staircase leads to the second floor, which offers a second primary suite with beamed tray ceilings, six windows, and an en suite bath with an alcove soaking tub and custom vanity. Three additional en suite guest rooms and a landing area with built-in seating complete this level. The 2,200 sq. ft. lower level continues the home's sense of luxury with a large media room, dining area lined with bookshelves, kitchenette with stone counters, and a second laundry room. A sixth bedroom, seventh bathroom, gym, custom built-in seating, and a linear wet bar complete the space. The landscape, designed by Charlie Marder, surrounds the property in natural beauty with hundreds of trees, including 30-foot Lebanese cedars, Asian pines, and gingkos. A heated gunite pool and spa are bordered by crepe myrtles, boxwoods, wisteria, and stone fruit trees. The patio offers multiple areas for entertaining, while a hidden path leads to an outdoor shower and a separate outbuilding housing a large sauna.

Set on a beautifully landscaped property in the sought-after Clearwater Beach area, this exceptional beach house offers the perfect blend of privacy, comfort, and effortless Hamptons living. Tucked away from the road and approached by a charming Belgian block-lined driveway, the home welcomes you with a covered front porch and sun-filled interiors throughout. The private backyard is a true retreat, featuring an oversized pool surrounded by mature specimen trees and lush gardens-ideal for relaxing or entertaining. Inside, the living room is anchored by a cozy wood-burning fireplace, while the newly renovated kitchen showcases quartz countertops, custom cabinetry, skylight and views of the backyard and pool. The kitchen flows seamlessly into the dining area with sliding glass doors leading to the outdoor barbecue area for easy indoor-outdoor living. A bright bonus room just off the kitchen offers additional space to unwind, with walls of windows overlooking the pool and gardens. The home includes two guest bedrooms and a full bath, while the spacious primary suite enjoys tranquil backyard views and an elegant en-suite bathroom. This home has it all including an attached one car garage and a lovely outdoor shower. Located just moments from the bay beaches, this East Hampton retreat is a rare opportunity to enjoy the very best of coastal living, whether entertaining guests or simply escaping to your own private oasis. Impeccably maintained with brand new Central Air Conditioning system installed in 2026 (includes warranty).

Just minutes from the center of East Hampton Village and sited on a quiet street in the Northwest Woods, this highly stylized one-story home is a stunning retreat for all seasons. Hardwood floors and high ceilings permeate throughout the house, and highlights include a fashionable entry foyer, a large living room with a wood burning fireplace, a stylish dining room, and an expansive kitchen that is outfitted with high-end appliances including a six-burner Bertazzoni double oven and range. Emphasizing privacy, the primary suite with renovated bath, two bedrooms, and an additional bath are on one wing of the house, with another bedroom and full bath on the other. Bonus spaces can be found throughout, including a convenient main floor laundry room, and there is a finished lower level with a full bath. A multitude of elegant decor items, including Murano glass chandeliers and Parisian Art Deco light fixtures, complete the interior space. A gated circular driveway showcases the front of the home, and the manicured grounds provide a sense of welcome. The backyard of this one-acre property is highlighted by a large heated pool, an expansive lawn, generous decking, perennial plantings of hydrangeas, and a covered pergola flanking the pool. A built-in barbecue, a wine refrigerator, and a pizza oven combine to provide ample space for outdoor dining and entertaining. Additional exterior features include an outdoor shower and an attached garage. This secluded locale offers the dual advantage of privacy while remaining close to East Hampton village restaurants, shops, transportation and beautiful ocean beaches.

Minutes from the bustle and charm of Sag Harbor Village, set on an exceedingly private and gated acre-plus flag lot with mature hedges, this immaculate 7 bedroom, 6500 square foot traditional checks all the boxes of a quintessential Hamptons summer home with a heated, gunite pool and spa, exceptional outdoor spaces, lined with hydrangeas, built-in BBQ grill kitchen, and an expansive finished lower level. Through the automated gate, a tree-lined approach leads to the handsome, white, shingled traditional with an attached 2-car garage. Adorned with shiplap, the bright, full height foyer creates a dramatic first impression. With lovely indoor and outdoor flow, the open concept floor plan offers a gourmet eat-in kitchen with an adjacent living room with fireplace and sitting area, with two sets of French door leading to the covered porch overlooking the pool area and rear grounds. A formal dining room with passthrough wet bar and wine storage serves the kitchen. A guest bedroom suite, pool full bath, foyer powder bath, expansive mud room, laundry room, and two-car garage completes the main level. Upstairs has a generous primary suite with luxurious bath including a freestanding tub and floating dual vanity. Three spacious en suite guest bedrooms supplement. The finished lower level features a gym, recreation area, and two bedrooms. Unique opportunity to own a turnkey home of excellent quality on a private acre-plus flag lot with a heated, gunite pool and spa and outdoor spaces fit for summer in the Hamptons.

Located on a quiet dead-end street just three miles from East Hampton Village, 6 James Street offers a peaceful retreat surrounded by natural beauty. Meticulously maintained and thoughtfully updated, this inviting three-bedroom home with two full baths and two half baths embodies the relaxed elegance of Hamptons living. The open, airy floor plan is filled with natural light and soaring ceilings, creating a warm and welcoming atmosphere throughout. Spacious living areas flow seamlessly together, offering an effortless setting for both everyday living and entertaining. Outdoor living is equally appealing. A stunning swimming pool is complemented by an expansive deck, providing ample space for lounging, dining, and enjoying long summer days in the sun. Tucked away in a separate private area, a fire pit gathering space and outdoor shower create the perfect setting for relaxed evenings and the quintessential East Hampton lifestyle. Offering comfort, privacy, and exceptional convenience, 6 James Lane is moments from East Hampton Village, ocean beaches, fine dining, and shopping, while enjoying the tranquility of its natural setting. A beautifully maintained home where every detail has been thoughtfully cared for and every space invites you to slow down and enjoy the best of the Hamptons.

Welcome to your dream home at 171 Norfolk Drive, East Hampton, NY, nestled within the highly coveted Clearwater Beach Association. This elegant and modern 5-bedroom, 4-bathroom residence, gut renovated in 2025, is a masterpiece of design and luxury. Spanning a generous 3,600 square feet on a .52-acre lot, this home blends contemporary aesthetics with functional elegance. Upon entering, you're greeted by a grand great room featuring high ceilings, a newly installed skylight, and sliders that open to a patio, seamlessly connecting indoor and outdoor spaces. A secondary sunken living room provides addiitonal living space for socializing or watching TV. The deck overlooks a stunning 20'x40' heated pool with an inviting cabana, perfect for summer relaxation. The primary suite, located in the left wing, boasts a walk-in closet and a spa-like ensuite bath. Opposite, two guest rooms share a well-appointed bath. The lower level introduces additional living room/ play room with a mounted TV, two additional bedrooms, a bathroom, a convenient laundry room, and a home gym. Enhancements include all-new 2023/2025 mechanicals: furnace, new central air for heating and cooling, hot water heater, and a Hydroteck water treatment system, a new 10-zone sprinkler system for the outdoor space. A new I/A septic system was installed in 2025. Outdoors, enjoy a front porch, large patio, and an enclosed shower, complemented by deeded marina access for boating enthusiasts. This meticulously maintained home is ideal as a rental investment, primary residence, or vacation retreat. Embrace modern living with timeless elegance at this spectacular East Hampton property.

This contemporary home displays style and function. It features an open layout in the main living area with a fireplace and abundant natural light. A seamless connection between the indoor and outdoor space. The primary ensuite bedroom is located on one side of the house while the two guest bedrooms and full bathroom are on the opposite side to allow for privacy. Hardwood floors throughout the house. Glass doors open to the large private deck and pool overlooking the treelined property. Beautiful landscaped grounds show off this unique property.

A tranquil flag lot with abundant natural light set on a generous acre plus on a flag lot tremendous privacy sits a lovely renovated ranch style home. An open floor plan with living, dining and kitchen. The abundance of natural light with wood burning fireplace fill the room. Three bedrooms and two full bathrooms balance the home. Off the open living area the sliding doors open up to the patio and pool area. All on a sprawling lawn overlooking reserve.

Tucked away on a quiet cul-de-sac near town and the bay, this beautiful traditional home sits within a private oasis. Designed by landscape architect W. Dean Gamolka, the grounds feature mature specimen trees, lush plantings, and a serene setting centered around a heated gunite pool-perfect for relaxing or entertaining. A garden path leads to the home, where thoughtful design and warm character abound. Inside, a mudroom with built-ins provides an easy transition from outdoors. The double-height living room is filled with natural light from expansive windows and opens to a deck, seamlessly blending indoor and outdoor living. A wood-burning stove adds comfort and charm, while the open layout connects the living and dining areas. An addition by architect Erica Broberg features a stunning eat-in kitchen with Caesarstone countertops, custom cabinetry, and high-end appliances. Quality finishes and built-ins throughout the home enhance both elegance and durability. The first floor includes a primary bedroom suite, while the second floor offers a cozy den, two additional bedrooms, and a full bath. The lower level provides flexible living space with a media area, gym, third bathroom, and ample storage. Outdoors, enjoy multiple gathering spaces, an outdoor shower, a service entrance, and a shed, all designed for privacy and ease. This is not a spec home, but a thoughtfully crafted residence, carefully designed and lovingly maintained, a rare offering to be enjoyed for years to come.

A remarkable Mid-Century Modern glass house that seamlessly blends architectural history with contemporary luxury. Originally conceived in the early 1960s and meticulously rebuilt and reimagined in 2018, with further expansion completed in 2021, the residence draws inspiration from the iconic Glass House of Philip Johnson. The home was born from a unique collaboration between Swedish architect Iver Loftving, an architect from Philip Johnson's studio who contributed to the renowned Seagram Building, and Athos Zacharias, an abstract painter and former studio assistant to both Jackson Pollock and Elaine de Kooning. The result is a timeless work of art where architecture, light, and landscape exist in perfect harmony. Offering three bedrooms and two bathrooms, the residence features approximately nine-foot ceilings throughout and an open-concept living space enveloped by walls of glass, wraparound windows, and sliding doors that dissolve the boundary between indoors and out. The primary suite serves as a tranquil retreat, complete with a wood-burning fireplace that adds warmth and character throughout the seasons. Mahogany decking surrounds the home, creating an effortless flow for entertaining and everyday living. Set on 0.6± acres of mature landscaped grounds, the outdoor experience is equally compelling, featuring a heated gunite pool, expansive mahogany terrace, a gravel patio dining area, and thoughtfully designed spaces for relaxation and gathering. Refined finishes and modern amenities include Bosch appliances, heated bathroom floors, Flos lighting, designer fixtures, and elegant Ann Sacks tilework throughout. Ideally situated moments from the historic Pollock-Krasner House and Preserve, and just a short drive from both East Hampton and Amagansett Villages, the property enjoys convenient access to marinas, acclaimed restaurants, boutique shopping, and some of the Hamptons' most beautiful ocean and bay beaches. A rare offering where architectural significance, modern comfort, and the Hamptons lifestyle converge.