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$5,499,999
6 Beds 8 Baths 986988 MLS
EXCEPTIONAL NEW CONSTRUCTION! Luxury Living at it's finest! Welcome to 20 Knollwood Road, Muttontown in the Jericho School District. Experience the pinnacle of luxury living in this newly built estate, offering approximately 7,000 square feet of refined design and superior craftsmanship by a highly regarded builder. Every inch of this home reflects meticulous attention to detail, from the bespoke millwork and custom paneling to the soaring ceilings and elegant herringbone flooring. A striking custom iron entry door welcomes you into a grand foyer, setting the stage for the home’s sophisticated yet inviting ambiance. The chef’s kitchen is a showstopper, featuring dual oversized islands, premium Sub-Zero and Wolf appliances, and effortless flow into formal and casual living spaces. Entertain with ease in the formal dining room or at the beautifully appointed wet bar with wine refrigeration. Designed for seamless indoor-outdoor living, French doors open to an expansive porcelain patio and a true resort-style backyard. Enjoy a fully outfitted outdoor kitchen, heated gunite pool with spa, and lush surroundings perfect for entertaining or relaxing in privacy. This impressive residence includes 6 generously sized bedrooms, all with en-suite baths, and a total of 7.5 designer bathrooms. The primary suite offers a luxurious retreat with spa-like finishes. Additional highlights include radiant heated bathroom floors, whole-house generator, central vacuum, Pella windows, circular driveway, and a sprawling lower level complete with a full bath and direct backyard access. A rare offering combining scale, sophistication, and immediate occupancy in one of Long Island’s most desirable locations.

20 Knollwood Road, Brookville

$5,499,000
6 Beds 6 Baths 1029122 MLS
Fields in the Foreground, A Legacy Behind the Gate Set beyond a private gate, this stunning estate offers expansive acreage and breathtaking farm field vistas, creating a rare retreat in the heart of Water Mill. Thoughtfully designed for both gracious entertaining and quiet relaxation, this six-bedroom, six-bathroom home is filled with natural light and beautifully appointed spaces. A grand double-height foyer welcomes you into an open and airy layout, where the great room with soaring ceiling and a fireplace flows seamlessly into the gourmet kitchen. Outfitted with top-tier Wolf and Sub-Zero appliances, a spacious center island with a second sink, quartz countertops, and a dedicated coffee station, this kitchen is both stylish and functional. A chic entertainer's bar, complete with a sink, dishwasher, refrigerator, ice maker, and wine cooler, enhances the home's effortless flow. The first floor features a private wing with the expansive primary suite, offering a spa-like bath with an air tub, radiant heated floors, and a loft space perfect for an office or library. Three additional first-floor bedroom optons provide comfortable accommodations for guests. Upstairs, two more ensuite bedrooms open to multiple decks overlooking the scenic farmland. The fully finished lower level offers endless possibilities, including an entertainment/TV area, gym, cedar wine storage, full bath, and private guest quarters. An oversized heated garage accommodates three vehicles, and a whole-home generator ensures uninterrupted comfort. Outside, discover a true Hamptons oasis, where a heated swimming pool with a brick patio is surrounded by lush English-style gardens and striking art sculptures. The outdoor kitchen is a chef's dream, featuring a brick pizza oven imported from Italy, a bar with hot/cold running water, two refrigerators, a smoker grill, and a two-burner stove with granite countertops. A water feature seating area and a two-season firepit with seating for 10+ complete the multiple outdoor entertaining spaces. Surrounded by horse pastures and scenic farm fields, this exceptional retreat blends luxury, privacy, and natural beauty, offering the ultimate Hamptons lifestyle.

652 Noyack Path, Water Mill

$5,499,000
9 Beds 8 Baths 1005247 MLS
Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. Inside, the richly paneled foyer and wide pegged oak floors set the stage for exquisite architectural details, including a sweeping staircase and intricate custom millwork. The first floor offers a seamless blend of grandeur and comfort. The magnificent living room and banquet-sized dining room both feature elegant fireplaces, while the gourmet kitchen boasts a spacious center island and a bright breakfast room. A butler’s pantry adds convenience, and the library, adorned with built-in bookcases and a fireplace, offers a cozy retreat. Additional highlights include a sunroom, two en suite guest bedrooms, a first-floor washer/dryer, and a powder room. Oversized windows throughout the home provide breathtaking views of the lush grounds. The expansive primary suite is a private sanctuary, complete with a fireplace, spa-like bath, dressing area, and a large balcony overlooking the manicured gardens. This level also features four additional bedrooms with two Jack-and-Jill baths, two additional fireplaces, a gracious hall bath, a gym/bedroom, an office/bedroom, and a second-floor laundry room. The lower level offers an abundance of recreational space, including a playroom, arts and crafts area, and a full bath. The exquisitely landscaped grounds provide something for everyone, offering endless opportunities for relaxation and entertainment. The sunken gardens, originally designed by renowned landscape architect Robert Ludlow Fowler Jr., are a marvel to behold. They gracefully lead the way to a serene 20x50 saltwater gunite pool that is complemented by a spacious, elegant pool house. Sports enthusiasts will appreciate the lighted clay tennis court and a heated, enclosed outdoor structure, perfect for squash or basketball. Adding to the estate’s appeal, a charming three-bedroom, two-bath guest cottage provides comfortable accommodations, while a three-car heated garage with a separate workroom ensures ample space for vehicles and storage. This extraordinary estate is a timeless masterpiece inside and out, seamlessly blending historic charm with modern refinement.

8 Stonegate Lane, Old Brookville

$5,498,000
7 Beds 8 Baths 1009813 MLS
Nestled on approximately 5 landscaped acres in Old Brookville, this distinguished estate offers exceptional space, privacy, and classic Gold Coast character. The property includes a stately main residence, a separate 3-bedroom guest cottage, and a pool house, providing flexible living and entertaining opportunities. The main residence offers approximately 5,764 square feet of living space with 7 bedrooms, soaring ceilings, hardwood floors, and elegant French arched windows that bring abundant natural light throughout the home. Expansive interiors overlook manicured grounds, gardens, and open scenic views. Recently renovated bathrooms blend modern updates with timeless design, while generously sized living areas provide comfort and functionality. The beautifully maintained grounds showcase seasonal landscapes and mature plantings, creating a serene setting year-round. Accessed through a gated entrance and private drive, this exceptional estate presents a rare opportunity to own a significant property in the desirable Village of Old Brookville.

952 Cedar Swamp, Old Brookville

$5,498,000
7 Beds 8 Baths 945621 MLS
Framing almost complete on this singular masterpiece! Ready Spring 2027 Time To Customize! An Exceptional New Construction Estate in Muttontown, located within the renowned Syosset School District. 'The Diamond' sets a striking new benchmark for refined living. This exquisite 8,000-square-foot residence offers seven bedrooms, 15 rooms and a fresh, contemporary layout designed for today’s most elevated lifestyles. Meticulously envisioned, 'The Diamond' reflects an extraordinary level of craftsmanship and an aesthetic precision that blends seamlessly with classic architectural detailing. Expansive sweeping light-filled interiors create a home that is both sophisticated and welcoming. Generous ceiling heights, dramatic walls of glass, and a seamless flow between indoor and outdoor spaces define the mansion. A grand courtyard entrance leads to custom-crafted oversized iron doors that dramatically unveil a breathtaking two-story entry foyer. The formal dining room features a connoisseur’s wine center with smoky glass accents that shimmer with understated drama, and a serving buffet crowned by a sculptural hanging etagere. The grand living room is anchored by a commanding two-sided modern fireplace that offers open views of the lush 2 acre property. The bespoke chef’s kitchen serves as a true centerpiece, equipped with premium Wolf and Sub-Zero appliances, custom cabinetry, and a spacious layout ideal for both everyday living and large gatherings. A fully equipped scullery kitchen adds an additional layer of convenience and sophistication for those who entertain on a grand scale. The main level further unfolds with guest quarters, a private study, state-of-the-art media room, and a secondary staircase. Ascending to the primary suite is to enter a private world of luxury: a serene balcony overlooking the property, a spa-inspired bath, a private sitting room, and multiple expansive walk-in closets befitting the most discerning wardrobe collections. The second level continues with a spacious lounge and four additional en-suite bedrooms, each a haven of comfort and privacy. Outdoor living is equally impressive, with fully approved plans to consider upgrades for a resort-style spa pool and an open-air pavilion complete with its own kitchen creating an alfresco realm of unparalleled leisure. The 10-foot lower level also stands ready to fulfill any vision. 'The Diamond' is not merely a home, it is a residence designed for the discerning, where high-style luxury meets the ease and functionality of everyday living.

50 Cecilia Drive, Muttontown

$5,495,000
4 Beds 6 Baths 1002247 MLS
HIDDEN GEM! RARE 1+ ACRE FULLY CLEARABLE EAST HAMPTON ESTATE 6,013 SF | 4 BEDROOMS | 6 BATHS | 40' GUNITE POOL | PRIVATE CUL-DE-SAC A rare opportunity to own over one acre of fully clearable property in East Hampton, privately situated on a quiet cul-de-sac just minutes from East Hampton Village. Offering an exceptional combination of privacy, space and proximity, this 6,013-square-foot residence features three levels of living and an expansive outdoor setting ideal for both relaxed living and entertaining. Built in 2017, the four-bedroom, six-bath home showcases a dramatic two-story great room with a wall of windows overlooking the 40-foot gunite pool and beautifully landscaped grounds. The open-concept main level includes a well-appointed kitchen with breakfast nook, spacious great room, separate dining room with coffered ceiling, serving pantry and laundry. The main level also features an en-suite bedroom, den and full bath, offering flexibility for guests or extended family, along with convenient access to the two-car garage. Upstairs, three additional en-suite bedrooms provide privacy and comfort, while a large den offers versatile space for an office, lounge or guest area. A second laundry room adds everyday convenience. The finished lower level, with 9-foot ceilings, a full bath and separate exterior entrance, provides exceptional flexibility for a media room, gym, recreation area, wine room or additional entertaining space. Outside, enjoy the privacy of the expansive grounds and a resort-style 40-foot gunite pool. With over one acre of fully clearable property, the estate offers a rare opportunity to enjoy significant land in a prime East Hampton location while providing excellent long-term investment potential. Just minutes from the restaurants, boutiques and beaches of East Hampton Village, 9 Briarsweet Lane offers a distinctive combination of substantial living space, privacy, acreage and proximity—making it an exceptional lifestyle property and a great investment in one of the Hamptons' most sought-after locations.

9 Briarsweet Lane, East Hampton

$5,495,000
5 Beds 6 Baths 961068 MLS
Bridgehampton Gambrel with Private Pickel & Padel Court The Ultimate Hamptons Lifestyle. This beautifully landscaped Gambrel sits on a private 1+/- acre lot, offering 5,000+/- sq. ft. of luxury living space and a brand-new private Piakcel/Padel court. The home features a dramatic double-height living room, a gourmet chef's kitchen, and five spacious bedrooms, including a grand upstairs master suite and two convenient first-floor guest rooms. Outdoor Paradise. Designed for resort-style living, the grounds feature a pristine pool, an expansive entertaining deck, and professional-grade Padel facilities-all framed by lush, mature landscaping for ultimate privacy. Unbeatable Location. Ideally situated just minutes from the vibrant villages of Bridgehampton, Southampton, and Sag Harbor, and within easy reach of world-renowned ocean beaches.

1366 Scuttle Hole Road, Water Mill

$5,495,000
944325 MLS
Stunning 18-Acre Estate in Lattingtown - A Unique Blend of History and Natural Beauty Discover an exceptional opportunity to own the last major parcel of the historic Underhill Farm, nestled within the prestigious Oyster Bay National Wildlife Refuge. This breathtaking 18-acre property set on two separate buildable approved lots on Factory Pond Road offers over 1,100 feet of pristine waterfront along Mill Neck Creek, providing an unparalleled setting for nature enthusiasts and history buffs alike. Embrace the serenity of this picturesque landscape, featuring a sweeping open field ideal for a variety of uses, from serene pastoral views to expansive gardens. A charming small wooded area adds a touch of tranquility, while mature trees offer privacy and an enchanting natural backdrop. Rich in history, this land was once home to a factory renowned for crafting Revolutionary War uniforms, imbuing the property with a unique historical significance. The legacy of this factory adds an intriguing layer to this already compelling site. This rare piece of real estate combines the allure of a wildlife haven with the charm of historical heritage, all set against the stunning backdrop of Mill Neck Creek. Whether you envision a private estate, a conservation project, or a legacy property, this unparalleled offering is a once-in-a-lifetime opportunity. Seize the chance to own a slice of Lattingtown's storied past and its spectacular natural beauty.

31 Factory Pond Road, Locust Valley

$5,495,000
5 Beds 4 Baths 918849 MLS
This elegant East Hampton Village home (circa 1870) underwent a gut renovation in 2023 under the acute eyes of architect Mark Zeff. Today, the home provides all modern amenities with special touches from years gone by. The large front porch welcomes you, the foyer offers a beautiful staircase with period detailing. Next is a spacious living room with original details and a fireplace, an enclosed sunroom overlooking the grounds offers a peaceful retreat. The gourmet kitchen is a chef's dream. A first-floor primary en-suite with walk through closet. On the second floor is another en-suite and three additional guest rooms with a full bathroom. The finished lower level offers additional spaces like a full bath, TV room, and office space. The heated gunite 13 x 40 pool is located next to a 13 x 7 spa overlooking the garden and pool house. Amenities include central air and beautifully finished pool house. Conveniently located close to the village restaurants and stores. Also, 1.26 miles to Main Beach.

44 Buell Lane, East Hampton

$5,490,000
6 Beds 6 Baths 845880 MLS
Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

89 Pound Hollow Road, Old Brookville

$5,350,000
5 Beds 6 Baths 1004280 MLS
Set on an acre on the prestigious and picturesque Elderfields Road in Manhasset, 100 Elderfields Road stands as a timeless example of classic farmhouse elegance. This stunning residence masterfully blends traditional charm with modern comforts, offering an expansive layout that includes five generously proportioned bedrooms and five-and-a-half baths. From the moment you step inside, the home’s thoughtful design and craftmanship become evident, catering seamlessly to both gracious entertaining and everyday living. Imagine hosting gatherings in the elegant dining room, illuminated by natural sunlight and complemented by the inviting warmth of a fireplace. For quieter moments, retreat to the cozy library, an ideal space for reading, or remote work.The heart of the home is the expansive chef’s kitchen, thoughtfully designed for both everyday living and entertaining, seamlessly flowing into an oversized inviting family room. Step outside onto the deck and take in the breathtaking views of the brand-new pool and pool house, surrounded by lush, meticulously maintained landscaping. The primary suite serves as a luxurious haven, boasting a soaring ceiling, a spacious walk-in dressing room, and an atmosphere of refined tranquility. The newly constructed pool house elevates outdoor living, complete with a full kitchen, bathroom, washer, dryer, and a convenient outdoor shower with built in cubbies. Enhancing the outdoor living experience, a fully equipped outdoor kitchen provides the perfect setting for summer barbecues and alfresco dining. Functionality has not been overlooked in this exceptional property with its mud room with custom built in lockers, ample storage and 2 car garage. Every detail has been thoughtfully curated to create a home that is as effortlessly livable as it is stunning. This rare offering combines classic farmhouse aesthetics with modern luxury, making it a truly exceptional opportunity. Don’t miss your chance to experience the unmatched beauty and versatility of 100 Elderfields Road.

100 Elderfields Road, Manhasset

$5,299,000
6 Beds 7 Baths 1044684 MLS
Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale rooms ideal for both everyday living and entertaining. A grand foyer introduces the home’s elegant flow. The formal living room includes a fully equipped custom marble wet bar, while the open-concept den is framed by floor-to-ceiling windows overlooking the backyard and anchored by a marble fireplace.The custom kitchen opens seamlessly to the formal dining room and is complimented by thoughtful storage cabinetry, a large center island, Gaggenau gas appliances, double Bosch dishwashers, and a Sub-Zero refrigerator/freezer. Upstairs, all five bedrooms are en suite, offering privacy and comfort for guests alike. The extra-large primary suite serves as a private retreat, featuring dual outfitted custom walk-in closets and a luxurious marble bath with a steam shower, soaking tub, and two vanities. A spacious laundry room is conveniently located on this level. A well-designed service area beyond the kitchen includes a mudroom, a walk-in pantry, a full bath, and convenient access to the three-car garage, back staircase, and steps leading to the basement. The main level also features a generously sized bedroom, ideal for guests or extended stays. Radiant heated floors are featured in all bathrooms and the mudroom. The outdoor space is equally impressive, featuring a heated 40' x 20' Gunite saltwater pool, paver patio, and outdoor kitchen—perfect for entertaining or enjoying the serene, private grounds.

63 Fruitledge Road, Brookville

$5,299,000
7 Beds 7 Baths 1005466 MLS
Modern Hamptons Elegance with Pool, Gym | Sag Harbor Recently constructed by renowned builder Farrell, this beautifully designed Sag Harbor home offers the perfect balance of luxury, comfort, and convenience just moments from the village, nearby marinas, and the ocean beaches of Bridgehampton. Thoughtfully designed across three finished levels, the residence features 7 bedrooms and 6.5 exceptional baths with sophisticated, current finishes and beautifully curated design throughout. The first-floor primary suite is a private retreat complete with its own office and direct access to the backyard patio and pool area. Upstairs, four ensuite guest bedrooms share access to a private terrace, while a conveniently located laundry room adds everyday ease. The heart of the home is the expansive open living space where a wood-burning fireplace anchors the great room, flowing seamlessly into the dining area and gourmet eat-in kitchen outfitted with top-of-the-line appliances and premium finishes. Oversized glass doors open beautifully to the resort-style backyard, creating an effortless connection between indoor and outdoor living. Designed for entertaining and relaxation alike, the outdoor space features a heated gunite pool, outdoor shower, grilling station, and multiple patios for dining and lounging. The finished lower level offers exceptional additional living space including a gym, media lounge, and recreation/game area, along with two additional bedrooms and a full bath. A staircase leading directly from the pool area to the lower level provides convenient access to the indoor gym after a swim or workout. Additional highlights include a mud room, 2-car garage, central vacuum system, and abundant storage throughout. Crafted with the quality, craftsmanship, and attention to detail synonymous with a Farrell-built home, this turnkey property is ideally positioned near the restaurants, boutiques, waterfront, and marinas of Sag Harbor Village while only minutes to the renowned ocean beaches of Bridgehampton. Sophisticated, stylish, and move-in ready, this is Hamptons living at its finest.

21 Lily Pond Drive, Sag Harbor

$5,295,000
6 Beds 9 Baths 1021182 MLS
Imagine an exclusive lifestyle redefined within a private HOA gated community, where absolute security meets unparalleled luxury on a flat, beautifully landscaped 2.53-acre parcel. This masterfully constructed 7,000-square-foot estate—boasting an impressive six bedrooms and seven bathrooms, each with their own private balcony—is defined by ultra-high-quality finishes throughout, including radiant heated floors, a central vacuum system, and a private elevator servicing all levels. The crown jewel of the residence is a first floor year-round indoor wellness spa complete with a pristine indoor pool, relaxing sauna, and steam room facilities. Designed for flexible multi-generational living, the home features dual (2) primary suites with private balconies and jacuzzi baths, a media room for grand entertainment, a designer eat-in chef’s kitchen anchored by a massive island, and a beautifully finished walk-out lower level. Entertain brilliantly on the expansive rear patio with outdoor kitchen and covered pavilion. Conveniently located just 11 minutes to the Long Island Expressway, this luxury home seamlessly blends elite architecture with a truly exceptional compound experience.

5 Farmwoods Lane, Upper Brookville

$5,295,000
5 Beds 7 Baths 951785 MLS
New waterfront estate in Remsenburg. This new construction is now complete and ready to show! Situated on 1.01 acres with incredible water views. This new state of the art 5,455 square foot home features a spacious floor plan, gourmet chef's kitchen, dining area, open living room, first floor ensuite bedroom, dedicated laundry room, and private den with a wet bar and fireplace. This home is complete with 7 sliding doors to the gorgeous outside, high-end finishes, appliances, and custom molding and carpentry throughout. On the second level you will find an impressive primary suite with cathedral ceilings, access to the grand balcony overlooking the water, 2 walk in closets, fireplace, custom ensuite bathroom with a steam shower, heated floors, and custom designed vanity. This level also features three additional ensuite bedrooms. The meticulously designed backyard is uniquely landscaped for privacy and showcases a gorgeous, heated waterside gunite pool and pool house as well as a new bulkhead on the canal. This private estate is ideally located just minutes to Westhampton Beach's Main Street and world class ocean beaches.This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

44 Club Lane, Remsenburg

$5,250,000
6 Beds 6 Baths 1037158 MLS
This custom-built 5000+sf waterview residence offers a rare combination of scale, thoughtful design, and modern coastal living in Montauk. The home features 6 bedrooms and 5.5 bathrooms, including four ensuite bedrooms, delivering flexibility for full-time living or a high-end retreat. Interior living space spans three levels with a finished lower level (1482sf) ideal for additional recreation and gym use, a 1509sf main level, and a 1770sf second floor. A cathedral-ceiling great room anchors the main level, with oversized sliding doors that open directly to the lush yard, custom mahogany deck, sparkling 30x16 pool, and separate semi-recessed hot tub—creating a seamless indoor-outdoor flow. The kitchen is outfitted with a premium appliance package, complemented by European white oak engineered hardwood flooring throughout the main living areas. Climate control is handled by a high-efficiency VRF heat pump system providing year-round heating and cooling. Outdoor amenities include a 30' x 16' swimming pool, custom mahogany deck, and a separate semi-recessed hot tub, designed for both entertaining and everyday enjoyment. Additional features include an attached two-car garage (445sf) and a well-planned site layout. The primary bath is uniquely finished with a textured feature wall, freestanding soaking tub, matte black fixtures, a private water closet, and a stained wood vanity—delivering a clean, modern spa experience. A refined, move-in-ready offering in one of Montauk’s most desirable neighborhoods. 25 S Duncan Dr is the latest offering from BuildWell, led by Evan Pargonas, reflecting a commitment to holistic design and construction that prioritizes sustainability and net-zero goals.

25 S Duncan Drive, Montauk

$5,250,000
6 Beds 10 Baths 1031994 MLS
Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

33 Chicken Valley Road, Old Brookville

$5,250,000
6 Beds 8 Baths 985121 MLS
An exceptional private brick estate compound set on approximately 7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property views, 6 spacious bedrooms with en-suite baths, 7.5 baths, large eat-in kitchen with generous counter space and storage, and full finished basement. Designed for both daily living and elevated entertaining, every space offers comfort, presence, and functionality. The meticulously designed grounds create a resort style setting with a custom 22,000 gallon koi pond, custom lighting, newly resurfaced Har-Tru tennis court, heated gunite pool, 8-person hot tub, pool house with kitchenette, full bath and changing room, custom outdoor kitchen, and premium speaker system inside and out. Complete with space for 10-cars, car lifts, and carport, this rare Upper Brookville estate delivers privacy, scale, luxury, and an unmatched indoor and outdoor lifestyle. A rare opportunity to own a private Upper Brookville estate with exceptional amenities and beautifully maintained grounds.

45 Wolver Hollow Road, Upper Brookville

$5,250,000
3 Beds 2 Baths 983585 MLS
A rare dual-waterfront opportunity in Southampton, this unique property offers direct frontage on both Little Peconic Bay and Fresh Pond, creating an exceptional setting with water on either side. With approximately 111 feet of sandy beach on the bay and a protected bulkhead with dock, the property provides immediate access to open water while also offering a more sheltered environment for boating and watersports. Enjoy long summer days on the beach with swimming, paddleboarding, and kayaking, followed by sunset views over Little Peconic Bay. From your dock, set out with ease to explore nearby destinations including Sag Harbor, Shelter Island, Robins Island and the North Fork. The existing single-story home features three bedrooms and two baths, with an open living, dining, and kitchen area oriented toward the water. Whether enjoyed in its current form or thoughtfully updated over time, the property also offers significant potential to expand or create a custom residence that fully takes advantage of its rare setting. Situated within a desirable waterfront community just minutes from Water Mill and Southampton Village, this offering presents a compelling opportunity for builders, investors, or end users seeking a unique combination of bayfront beach and protected dockage in the Hamptons. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

21 E Shore Drive, Southampton

$5,200,000
5 Beds 6 Baths 910335 MLS
Water Island Awaits. Two Iconic Buildings. One Majestic View. Location- Tucked between Fire Island Pines and Davis Park lies Water Island. With only 48 homes adjacent to the protected Fire Island National Seashore; Water Island creates a unique sense of remoteness and natural beauty — a true retreat for those seeking to unwind in quiet luxury. This secluded estate offers 200 feet of unobstructed Atlantic Ocean frontage; rare privacy and direct access to pristine beaches, all within an easy commute from New York City. Inspiration- A masterpiece of coastal design, this home has earned a place in the pages of several premier luxury publications. Designed by the legendary Scott Bromley of Bromley Caldari Architects with influence drawn from the craftsmanship and philosophies of George Nakashima and Hans Wegner, this expansive retreat is a study in balance — where modernist clarity meets organic warmth. The design embraces a sense of quiet luxury drawn from these iconic places: the barefoot elegance of Parrot Cay, the raw natural beauty of Big Sur, and the sculpted minimalism of Amangiri. Main House- The One-Bedroom Main House, a private and reimagined sanctuary for the Owners, sits nestled in the dunes. Inside, a warm composition of cedar and teak woods, white walls, and diffused light creates a tranquil atmosphere. The first floor serves as a serene sleeping suite, where spa-like bathing spaces are seamlessly integrated into the flow of everyday living. Above, the second floor opens fully to the landscape with expansive floor-to-ceiling windows and sliding glass doors that dissolve the boundary between indoors and out. Here, the Atlantic Ocean becomes both backdrop and focal point — a constant, calming presence, framed by architecture that gives it space to breathe. The dramatic cathedral ceiling in the main living space is punctuated by an oversized Noguchi hanging globe lighting fixture. Discover an airy chef’s kitchen where clean lines meet organic textures. Showcasing handcrafted wood cabinetry paired with caesarstone countertops – blending modern comforts like Sub-Zero, Wolf and Miele appliances. Oriented toward the coastline, the main living and dining spaces maintain a constant connection to the ocean, making it an integral part of the home’s daily life. Guest House- A meandering path through the sand joins the main house with the four-bedroom four bath guesthouse on the adjacent lot, a relaxed social hub featuring a bar, sun decks, an outdoor kitchen, and a pool — all designed to encourage barefoot living and effortless hospitality. From the moment you step inside the guest quarters you are enveloped by the integration of architectural elements – cool stainless steel, warm-toned woods, and white walls and ceilings – creating a layered, modern aesthetic. This interplay of textures brings depth and sophistication, blending functionality with high design for a space that feels both curated and comfortably livable. Details: 0 Charach & 1 West Walk Water Island, Fire Island, NY Two Structures on two adjacent lots (Total lot area - 10,000 sqft.) Connected by a Stone Path between the two Main House - 1 Bed 1.5 Bath Residence (Approx. 2,100 sqft.) 7.5’ x 5’ Custom Concrete Collaborative Panel Jacuzzi Guest House - 4 Bed 4 Full Bath Residence (Approx. 1,500 sqft.) 25’ x 9’ Custom Gunite Pool Outdoor Kitchen w/ Weber Gas Grill; Under Counter Refrigerator & Ice Maker Exterior: Clear Cedar 1X6 Clapboard Exterior Siding Mahogany and Cedar Clad Decks with Ipe hardwood trim accents Reilly double insulated, wind-borne debris rated Windows & Doors ‘Invarimate’ Contrarian Stainless Steel Roof System Interiors: Gothic European Oak Wood Floors White Washed 1X6 Clear Cedar Tongue & Groove Walls w/ Ipe hardwood trim accents Custom Designed Wood Veneer Cabinetry Caesarstone Kitchen Countertops Custom Ammonite Stone Bathroom Countertops Custom Teak Wood Sink Vessels

Charach & 1 West Walk, Water Island

$5,180,000
3 Beds 2 Baths 1045420 MLS
A Private Dunes Retreat in Amagansett Behind a charming wooden gate, on a quiet Amagansett Dunes lane, lies a world of its own, just a short distance from the ocean beach. At the heart of the property, a saltwater gunite pool is bordered by a bluestone patio on one side and lushly landscaped lawn on the other, evoking a private resort more than a backyard. Dual heating systems extend the swimming season of this 25' x 15' pool to six months or more. To the side of the house, an oversized enclosed outdoor shower, multiple beach-gear sheds, and a full-house generator handle the practical side of Hamptons living. Then comes the real magic: at the back of the property, a 2.5-acre dune preserve unfolds in complete privacy, with no neighbors in sight. At nightfall, the star-filled sky overhead is something guests often call unforgettable. Inside, the home is thoughtfully designed as an "upside-down" house, placing main living spaces upstairs to capture sweeping dune views from a wraparound porch off the open-concept great room with fireplace, flowing easily from a light-filled, renovated kitchen to a private outdoor space for grilling and entertaining. The primary suite occupies the second floor with an en-suite bath and radiant heat. Downstairs, antique brick floors with radiant heat warm two additional bedrooms and a full bath, along with a wood-burning stove, a kitchenette, laundry room, and a flexible bonus room currently used as an office. Ample space remains to expand to a fourth bedroom and third bath, if desired. Turnkey and move-in ready - a rare combination of true privacy, resort-style outdoor living, and proximity to the ocean, almost impossible to find together in the Dunes.

18 Cliff Road, Amagansett

$5,150,000
8 Beds 9 Baths 951556 MLS
Be the first to enjoy this outstanding newly constructed home located in the highly desirable Village of Quogue. The spacious 6741+/- sq ft residence, spans three levels (including 1966 sq ft finished lower level), and features 8 bedrooms and 9 baths. Sited on 1.29 lush, park-like acres, this exceptional property showcases a 20x40 heated salt-water gunite pool, complemented by an elegant pool house. Expansive mahogany decking and a large stone patio create an effortless indoor-outdoor lifestyle, while the generous grounds offer the rare opportunity to accommodate a private tennis court. Thoughtfully designed, the home's meticulous craftsmanship is on full display with 4" white oak flooring and sleek transitional trim throughout. Upon entering, you'll be greeted by a stunning two-story foyer with soaring ceilings. The open layout is bathed in natural light from multiple doors and deep windows that look out on the lush grounds. The great room provides a spacious sitting area to gather by the gas fireplace and a generously sized dining space that seamlessly flows into the custom chef's kitchen. A culinary masterpiece, the kitchen features a large island with seating, top-of-the-line appliances, quartz countertops, a walk-in pantry, and a convenient wet-bar with open shelving and a wine and beverage refrigerator. A formal dining room offers an additional option for entertaining. In addition to a junior primary suite with its own bath, the first floor offers an attached oversized two car garage, mudroom, laundry room, full bathroom, and dedicated closet that can accommodate a three-floor elevator. At the second-floor landing, a breathtaking two-story window fills the space with sunlight while framing a picturesque view beyond. A generously sized primary suite is the ultimate retreat and features two walk-in closets, and a bathroom with a separate shower, soaking tub and two vanities. The primary also has access to its own private rear deck overlooking the grounds. Three en suite guest bedrooms all with their own bath and large designer closets offer plenty of accommodation options for guests. An additional bedroom/bonus room includes a full bath and open space for a bunk room, playroom or gym. Completing this floor is a second laundry room. The finished lower level includes two additional bedrooms, a full bathroom, and an expansive recreational area that offers numerous possibilities for a home theater, gym, and playroom. A walk out entrance connects the lower level to the inviting pool area and landscaped backyard. In addition to the stunning gunite pool, the pool house is equipped with a full bathroom, wet bar entertaining area, outdoor shower, and a covered patio. Located on a quiet street, this home offers close proximity to Quogue's shops and ocean beaches, providing a serene and private setting. Don't miss the opportunity to make this Quogue gem your own.

34 Old Main Road, Quogue

$5,100,000
5 Beds 4 Baths 1009823 MLS
OCEAN FRONT SEAVIEW. 5 bedroom 2 bathrooms and 2 powder rooms. Gym, veggie garden, guest house (this is included in the 5 bedroom 1 half bath) chefs kitchen, laundry room, storage, dog run. This house is truly a home. Views, and privacy is rare on the ocean, yet this beauty has both. A true gem in the heart of seaview, with extra artistic style at every glance. Shade, sun, views, quiet, entertaining space, this deck has it all. You need to come tour this one, in order to really “get it”. 7x7 dunk pool can be added. Taxes approx 15k insurance “self-insured” SV Assn dues: $6,001.38 General Interior • Leight kitchen cabinetry (2015) • Enclosed Pantry • SubZero fridge/freezer-drawers • Integrated lighting • integrated pull-outs • New windows and sliders (2024) • Ceiling fans in 4 BRs Master Bedroom Suite (full renovation 2021) • New Skylight • Custom bathroom cabinetry • Custom walk-in closet • Custom desk and pet crate • Dual flush Toto washlet • Walk-in jet tub within shower enclosure • Heated shower floor • Heated main floor • Dual sink with slant-drain Shoulder Season add-ons • Heated floors in kitchen and 4 baths • HVAC system installed 2020 • Deck radiant heat for dining Guest Cottage • Complete refurbish with half-bath and closet space • Heated bathroom floor • Toto dual flush washlet • New windows Landscaping • Raised beds for both decorative and vegetable growing • Four-zone watering system w mobile app control • Interior deer-proof gardening space • Primary/secondary composting bins Other • New main deck, clear cedar, including all new posts (2024) • Two-level deck providing choice of privacy or elevated ocean view • All north-facing windows replaced 2025 • All lower level ‘storage areas’ waterproofed and painted (2025) • Heavy-duty gym flooring installed throughout 3 ‘rooms’. (2025) • New roof on main house (2019) • Solar panels providing 90-100% power to run the home (2019) • Two Rheem brand Gladiator 55 gal water heaters w/ leak detection and auto shutoff (2025)

61 Evergreen Avenue, Seaview

$5,100,000
5 Beds 5 Baths 1017106 MLS
Perched on 2.5 private waterfront acres in the prestigious Village of Old Field, this extraordinary North Shore estate captures sweeping panoramic views of Long Island Sound and Smithtown Bay, offering a rare blend of luxury, privacy, and timeless coastal elegance, and includes 280 feet of water frontage. The approximately 6,000-square-foot residence features five bedrooms and five baths, thoughtfully designed to maximize both grand-scale entertaining and comfortable everyday living. A dramatic great room with fireplace, formal dining room, gourmet chef's kitchen, custom granite and cherrywood bar, wine cellar, and private theater create an unparalleled lifestyle experience. Walls of glass frame breathtaking water views from nearly every principal room, while exquisite craftsmanship and sophisticated architectural details elevate the home's refined character. Outside, resort-style grounds unfold with a stunning Gunite, Aquabrite pool and waterfall, pool house, expansive patios, lush gardens, and sprawling lawns that lead to the waterfront. Spectacular sunsets paint the sky each evening, creating a setting that is both serene and unforgettable. Located within the acclaimed Incorporated Village of Old Field and moments from beaches, yacht clubs, and the historic charm of Setauket, this is a rare opportunity to own one of the North Shore's most captivating waterfront estates.

14 Woodcock Lane, Old Field

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