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$2,399,000
6 Beds ⋅ 5 Baths ⋅ 1046808 MLS
Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with expansive living spaces filled with natural light of generous proportion and seamless indoor-outdoor flow creating a tranquil retreat just moments from the harbor, beaches, yacht clubs, vineyards and nature preserves. Set on two private beautifully landscaped level acres of property designed for both everyday enjoyment and sophisticated entertaining. This private estate seamlessly blends timeless elegance, modern luxury, and resort-style living. A grand two-story foyer introduces the home's sophisticated interiors, where soaring cathedral ceilings, gleaming hardwood floors, abundant natural light, and exquisite architectural details create an atmosphere of warmth and refinement. Thoughtfully updated throughout, every space has been designed with both everyday comfort and effortless entertaining in mind. The recently renovated chef's kitchen serves as the heart of the home, featuring a dramatic Crawford ceiling, custom crown and box moldings, quartzite-topped center island, and a suite of premium appliances including a Sub-Zero refrigerator, Bosch range, double ovens, microwave drawer, and dishwasher. The kitchen flows seamlessly into the impressive great room, highlighted by a floor-to-ceiling stone wood-burning fireplace and walls of windows overlooking the picturesque grounds. Elegant entertaining spaces continue with a gracious formal living room accessed through glass pocket doors, and a spacious dining room perfectly suited for hosting intimate gatherings or larger celebrations. The main level offers five generously proportioned bedrooms and three full bathrooms, including two recently renovated baths appointed with refined finishes. Upstairs, an expansive loft with hardwood floors overlooking the great room provides additional living and entertaining space and leads to the luxurious primary suite. This private retreat features hardwood flooring, custom closets, detailed millwork, and a stunning newly renovated spa-inspired bath complete with a soaking tub, oversized glass-enclosed shower, dual vanity, and exquisite Italian tile. The outdoor setting is nothing short of extraordinary. Professionally landscaped grounds surround a tranquil in-ground pool, complemented by multiple paver patios designed for elegant outdoor entertaining and relaxation. A sprawling Trex deck extends nearly the entire length of the home, creating a seamless connection between indoor and outdoor living. Additional highlights include a fully finished lower level with a full bath, offering exceptional flexibility for recreation, fitness, guest accommodations, or extended living space. Car enthusiasts will appreciate the rare offering of four garage spaces, including two attached and two detached garages. Recent improvements include extensive interior and exterior painting, newer windows, newer roof and skylights, custom closet systems, wood flooring throughout most of the house and numerous thoughtful upgrades throughout. A wonderful opportunity awaits for you to own this property and reap the rewards of resort living in the White Spruce Farm Community within the Village of Head of the Harbor. A must see! *Taxes Include Village Taxes of $3,199

15 The Chase, Head Of Harbor
$6,150,000
5 Beds ⋅ 5 Baths ⋅ 1037500 MLS
Where the Cotswolds Meets the Hamptons The Cotswolds meets the Hamptons in this extraordinary property, gracefully set on a secluded acre in the coveted Hamptons Farm Estates section of Bridgehampton. Rich in character and timeless elegance, this exceptional home seamlessly blends old-world craftsmanship with refined Hamptons luxury. The beautifully appointed four-bedroom, three-full and one-half bath residence is designed for effortless living and sophisticated entertaining. At its center is a spectacular chef's kitchen featuring new premium appliances, including a Wolf six-burner range with griddle, double wall ovens, two dishwashers, a large farmhouse sink, an additional prep sink, and a wine refrigerator. A stunning marble center island is complemented by elegant soapstone perimeter countertops, creating a kitchen that is as beautiful as it is functional. Throughout the main level, rich reclaimed wood flooring from Gibraltar lends warmth, history, and an unmistakable sense of authenticity. The inviting living room is anchored by a beautiful wood-burning fireplace and crowned by a magnificent coffered ceiling, creating a warm yet sophisticated gathering place throughout the seasons. Just beyond, a charming sunroom offers a tranquil space to read, relax, or simply take in the beauty of the surrounding gardens. The elegant dining room is equally impressive, featuring custom-designed windows that frame picturesque views of the grounds and a beautifully detailed 12 ft. tray ceiling. Bathed in natural light, it opens through sliding glass doors to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. A classic wraparound front porch welcomes guests, while the exquisite screened porch and expansive stone patio provide idyllic settings for entertaining or quiet moments overlooking the pool and lush, mature landscaping. The serene primary suite is a true retreat, complete with its own gas fireplace and a luxurious spa-inspired bath featuring a soaking tub, elegant stone walk-in shower, and radiant heated floors. One of the guest bedrooms opens onto a spacious private deck overlooking the beautifully landscaped grounds-a spectacular place to enjoy morning coffee or unwind while watching breathtaking Hamptons sunsets. The finished lower level offers additional living and recreation space, while a beautifully private detached guest cottage with its own sleeping quarters, kitchen, and full bath provides luxurious accommodations for family and friends. Completing the property are a detached two-car garage, a charming potting cottage thoughtfully converted into additional entertaining space, a spacious circular driveway with generous parking, and an extraordinary sense of privacy rarely found in such a central location. Perfectly positioned in the heart of Bridgehampton the home is just moments from world-renowned equestrian facilities, the charming villages of Bridgehampton and Sag Harbor, pristine ocean beaches, acclaimed restaurants, vineyards, and upscale boutiques, offering the very best of Hamptons living. More than a house, this is a home-one that has been thoughtfully curated, beautifully lived in, and designed to bring people together. Every room reflects warmth, craftsmanship, and a sense of belonging, while every outdoor space invites relaxation and connection. Rarely does a property possess such genuine soul. Timeless and elegant this is a place where memories are made and traditions begin.

245 Meadows W, Bridgehampton
$4,499,000
4 Beds ⋅ 4 Baths ⋅ 1029440 MLS
First time to the market, this rare expression of modern coastal luxury is an extraordinary waterfront estate on prestigious Rampasture Point, masterfully reimagined to offer an unparalleled living experience overlooking the tranquil waters of Tiana Bay. Every finish, texture, and architectural detail have been intentionally selected to create a residence that is as timeless as it is breathtaking. From the moment you arrive, the home's striking architectural presence commands attention. A magnificent, oversized pivot entry door creates an unforgettable first impression, setting the stage for the sophisticated interiors beyond. It immediately reflects the home's exceptional craftsmanship and design. Inside, the impeccably designed living space unfolds beneath soaring ceilings and walls of glass that frame spectacular waterfront vistas from nearly every room. Thoughtfully curated by a luxury interior designer, it showcases wide-plank white oak flooring, custom architectural millwork, exquisite Phillip Jeffrey designer wallcoverings, statement lighting, and handcrafted details that elevate every space into a work of art. The chef's kitchen serves as the true centerpiece of the home. Custom inset cabinetry, dramatic honed quartz countertops, handcrafted range hood, Thermador appliances, and sophisticated coffee bar create a space equally suited for quiet mornings and elegant entertaining. The kitchen flows into the dining and living areas, where uninterrupted views of Tiana Bay become part of the home's everyday backdrop. Anchored by a natural gas fireplace, the living room exudes warmth and sophistication. Bespoke built-in shelving has been thoughtfully designed to showcase artwork, books, collections, and sculptural decor. Designed for effortless modern living, this four-bedroom, three-and-a-half-bath smart home seamlessly blends cutting-edge technology with timeless elegance. Motorized shades throughout provide privacy and convenience while allowing the breathtaking waterfront scenery to remain the focal point. The primary suite is a sanctuary unlike any other. Soaring ceilings, designer lighting, and expansive walls of glass create an atmosphere of serenity and sophistication. Begin each morning at your private coffee bar before stepping onto your balcony, where spectacular sunrises over Tiana Bay become part of your daily ritual. The spa-inspired primary bath offers a retreat worthy of a five-star resort. A freestanding soaking tub is perfectly positioned beside a picture window overlooking the open bay. Luxury entertaining extends throughout the home with multiple beverage stations, including two built-in temperature-controlled wine refrigerators serving both the indoor and outdoor living spaces. Outside, resort-style living reaches its finest expression. Expansive waterfront decking seamlessly extends the home's living space, offering a fully equipped outdoor kitchen, elegant dining area, generous lounge seating, multiple gathering spaces, and an exceptional gazebo that provides the perfect setting for afternoon relaxation or sunset cocktails. Every outdoor space has been thoughtfully designed to celebrate the beauty of waterfront living. Beyond the deck, your own private beach awaits, offering direct access to kayaking, paddleboarding, boating, swimming, and peaceful walks along the shoreline. A whole-house generator provides year-round comfort ensuring uninterrupted enjoyment of this remarkable waterfront estate. Perfectly positioned just minutes from the world-renowned white sand beaches of Dune Road, premier marinas, waterfront dining, boutique shopping, and the very best of the Hamptons lifestyle, this exceptional residence represents one of Hampton Bays' most compelling waterfront offerings. This is more than a home—it is a legacy property. A designer waterfront estate where architecture, craftsmanship, and nature exist in perfect harmony, creating a lifestyle that is both effortless and extraordinary.

29 Tiana Circle, Hampton Bays
$6,999,000
7 Beds ⋅ 6 Baths ⋅ 1023535 MLS
Tucked away on four spectacular acres overlooking a tranquil freshwater pond, this extraordinary Cold Spring Harbor estate offers a rare balance of complete seclusion and effortless convenience. Hidden behind a gated entrance and surrounded by nature, the property evokes the feeling of a private country retreat while remaining just moments from the charming village, harbor, acclaimed schools, and every amenity that makes Cold Spring Harbor one of Long Island's most coveted communities. Extensively rebuilt and expanded in 2019, the residence seamlessly blends timeless architecture with sophisticated modern design. A dramatic two-story foyer welcomes you into the heart of the home, offering stunning sight lines through the residence to the resort-like pool and picturesque grounds beyond. The magnificent two-story great room is centered around an impressive floor-to-ceiling stone wood-burning fireplace and flows effortlessly into the open-concept living and dining spaces, designer kitchen, and elegant bar area. Expansive windows flood the interiors with natural light while framing breathtaking views of the surrounding landscape. Designed for both grand entertaining and comfortable everyday living, the home offers an exceptional collection of gathering spaces. A dedicated first-floor media room with a 4K projector delivers an immersive cinematic experience, while the inviting billiard room features its own stone fireplace, reclaimed barn wood walls and beams, creating the perfect setting for entertaining. Modern conveniences include a Sonos sound system with integrated speakers in the kitchen, great room, and pool area, providing effortless indoor-outdoor enjoyment. The thoughtfully designed second level showcases rich walnut flooring throughout and is highlighted by the luxurious primary suite. A private sanctuary featuring soaring vaulted ceilings, oversized walk-in closets, a private balcony, and a spa-inspired en suite bath complete with a soaking tub, sauna, and refined finishes with the addition of seasonal water views of the harbor make this retreat truly exceptional. Five additional bedrooms and a conveniently located laundry room complete the second floor. Two of the secondary bedrooms are tucked away in their own private wing, separated by an inviting sitting area and served by a private rear staircase, creating an ideal layout for guests, extended family, or multigenerational living while preserving comfort and privacy. The outdoor living experience is equally impressive. A saltwater Gunite pool with a sunken spa is surrounded by lush landscaping and expansive entertaining spaces, offering the ultimate setting for relaxation. Gentle natural springs wind through the property, adding a peaceful soundtrack to this remarkable setting. A breezeway with double electric entry doors enhances both convenience and security to inner courtyard and three-car garage. Finished with a classic cedar shingle roof and crafted with exceptional attention to detail throughout, this remarkable estate presents an exceedingly rare opportunity to own one of the North Shore's most private and captivating residences. Here, the sounds of flowing springs, the beauty of the freshwater pond, and an unparalleled sense of privacy create the feeling of being a world away yet the vibrant waterfront village and everyday conveniences of Cold Spring Harbor remain just minutes from your gate.

36 Spring Street, Cold Spring Hrbr
$4,750,000
5 Beds ⋅ 8 Baths ⋅ 1009662 MLS
Located in the heart of Westhampton Beach Village, this extraordinary 9,500-square-foot estate is set on 1.20 beautifully landscaped acres, offering a rare blend of historic grandeur, modern comfort, and the quintessential Hamptons lifestyle. Rich in character and timeless elegance, the residence is introduced by a grand foyer that immediately sets the tone for the home's impressive scale. Beyond, an oversized historic ballroom serves as the centerpiece of the estate, featuring soaring ceilings, a wood-burning fireplace, floor-to-ceiling windows, and custom built-in bookshelves. Originally dating to the 1800s, this remarkable space is steeped in history and craftsmanship, with rich walnut millwork and architectural details that make it truly exceptional. Evoking the glamour and sophistication of the Great Gatsby style, the ballroom is an extraordinary setting designed for unforgettable entertaining and effortlessly accommodating everything from intimate gatherings and elegant dinner parties to grand-scale celebrations and lavish soirees. The main level offers a spacious living area, billiard room, full bath, an additional living space complete with a kitchenette and bar and a bedroom with en suite bath. An oversized formal dining room and separate breakfast area provide exceptional settings for hosting, while the den/great room, anchored by a wood-burning fireplace, creates a warm and inviting retreat. The chef's kitchen is appointed with granite countertops, maple cabinetry, an induction oven, and stainless-steel appliances. A laundry room and powder room complete the first floor. The second level is thoughtfully arranged into two distinct wings. The west wing guest quarters feature an own foyer leading to a full bath, sitting area, and bedroom. This wing also includes an office opening to an own balcony overlooking the beautifully manicured grounds, along with a sitting room, full bath, additional bedroom, and balcony access. The main second-floor wing showcases an expansive primary suite designed as an inclusive sanctuary, featuring a spacious sitting room, wood-burning fireplace, walk-in closet, spa-inspired bath, and a dramatic spiral staircase leading to a lofted retreat. An additional office completes this wing. A second primary suite offers its own sitting area and en suite bath, providing luxurious accommodations for all. Blending timeless Hamptons elegance, architectural character, and exceptional scale for both grand entertaining and private living, this distinguished estate presents a rare opportunity to own one of the area's most unique residences. Nestled among mature specimen trees and picturesque landscaping, the property also features a 20' x 40' in-ground pool, creating a tranquil resort-like setting for relaxation and entertaining. Set within one of Westhampton Beach’s most desirable locations, moments from renowned beaches, acclaimed dining, and boutique shopping, the property embodies the very best of Hamptons living.

45 Beach Lane, Westhampton Beach
$1,890,000
4 Beds ⋅ 3 Baths ⋅ 1008414 MLS
Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship found throughout. Features include oak hardwood floors, solid hardwood interior doors, custom millwork, marble and tile mosaics, a custom detached 2-car garage with handcrafted garage doors built by the homeowner and features its own electrical panel. The fully finished basement includes an outside entrance, laundry area and epoxy flooring. The large, open kitchen includes custom cabinetry, granite countertops, stainless steel appliances, and custom designed tile work. A breathtaking handcrafted marble fireplace with carved lion statuary serves as the centerpiece of the home and features a heat-circulating system with dedicated venting to the primary suite above. Built with 2x6 construction and blown-in insulation for exceptional energy efficiency, the home was also strategically positioned above grade to promote superior drainage. Smart home features include remote thermostat controls with separate zones in each bedroom and an automatic leak-detection water shutoff system. Extending the living space outdoors, a covered patio overlooks the private grounds and is already pre-wired for cable and has a water line in place, providing a seamless opportunity to create the outdoor kitchen and entertainment area of your dreams. From the handcrafted architectural details to the thoughtful engineering and modern conveniences, no expense was spared in creating this truly exceptional residence. A rare opportunity to own a luxury home unlike anything else on the market.

225 Old Willets Path, Smithtown
$2,699,000
6 Beds ⋅ 6 Baths ⋅ 980502 MLS
Exquisite Resort-Style Retreat in East Quogue. Recently renovated, turn-key estate set on a sprawling 1.6-acre lot at the end of a private, long driveway, this home offers an unparalleled resort-like setting designed for both grand entertaining and serene relaxation. Spanning 4,100 square feet of meticulously crafted living space, the interior flows seamlessly from one designer room to the next. Chef’s kitchen leads to a bright, inviting breakfast room right next to the formal dining room. Additionally, the first floor offers a large living room with fireplace as well as a private office and den. The second floor offers the large primary bedroom plus junior suite as well as two more bedrooms that share a bathroom, making a total of four bedrooms and three full bathrooms on the second floor. The basement is an additional 2,000 square foot of finished space with plenty of versatility. This level includes two bedrooms with egress windows, a full bathroom, a separate walk-out entrance, a home gym area, and a family room. Located above the detached two-car garage is also a full bonus apartment with kitchen and full bathroom. The expansive backyard has a pristine heated saltwater pool that serves as the centerpiece of the outdoor oasis. There's also basketball with ample room remaining to add a tennis court. True Virtual Tour available upon request.

26 Box Tree Road, E. Quogue
$1,850,000
3 Beds ⋅ 2 Baths ⋅ 976881 MLS
Wake up to beautiful waterfront views in this custom-built European-style home located in desirable West Islip. This elegant 3-bedroom, 2-bath residence offers approximately 2,000 sq ft of thoughtfully designed living space featuring radiant heated floors and light-filled interiors with water views from multiple rooms. The property features a multi-level backyard setting ideal for outdoor enjoyment, entertaining, or relaxing while taking in scenic sunsets. Boating enthusiasts will appreciate the opportunity for private dockage with access to the Great South Bay and convenient boating routes toward Fire Island. Blending timeless architectural character with modern comfort, this home offers a unique coastal lifestyle experience while remaining conveniently located near shopping, dining, transportation options, and other local amenities. This waterfront residence presents an excellent opportunity for year-round living or a weekend retreat.

238 W Islip Road, West Islip
$2,999,000
5 Beds ⋅ 5 Baths ⋅ 950375 MLS
Discover your dream Hamptons retreat in this exceptional five bedroom residence where sophisticated living meets everyday comfort. This stunning home spans an impressive 5,400 square feet of thoughtfully designed space, showcasing meticulous craftmanship throughout every corner. Inside find a welcoming living room with cathedral ceilings flowing seamlessly into an open kitchen with great room with fireplace, along with a butler's pantry and breakfast area offering casual mornings with your coffee while the formal dining room awaits your dinner parties. The primary suite is nothing short of spectacular featuring its own sitting room complete with a second fireplace - because sometimes one just isn't enough. There is also a spectacular primary bath with soaking tub and walk in shower along with his and her throne rooms. Four additional en-suite bedrooms ensure everyone enjoys their privacy, while a dedicated office/den provides the ideal work from home sanctuary. The expansive basement boasts impressively high ceilings and an outside entrance offering endless possibilities for recreation and storage areas. A two car garage keeps your vehicles protected year round. Outside the magic continues with a sparkling inground pool , relaxing hot tub and dedicated play area set on a generous lot. The covered porch and elegant paver patio create perfect spaces for al fresco dining and lazy summer afternoons. The neighborhood delivers everything you'd expect from Hamptons living - minutes from East Landing Beach, Good Ground Park, Red Creek Park and the charming Canoe Place Inn The nearby train station makes commuting surprisingly manageable. This is more than a home; it's the lifestyle you've been searching for. Don't miss the opportunity of a lifetime1

10 Bay Woods Drive, Hampton Bays

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.