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43 Tarpon Road, E. Quogue
$3,850,000
5 Beds ⋅ 5 Baths ⋅ 1055494 MLS
Luxurious Bayfront Haven with Unmatched Water Views, Pool & Dock. Experience the pinnacle of coastal elegance in this extraordinary two-story bayfront home, within the sought-after Shinnecock Shores private community. Offering 5 bedrooms and 4.5 baths, set amidst over 150 feet of canal frontage and 100+ feet of stunning bay frontage. This property is a true gem for those seeking the perfect blend of luxury and waterfront living. On the first floor, two inviting guest ensuites await, including an oversized suite with double sliding doors leading directly to the expansive pool deck—perfect for hosting guests or enjoying tranquil afternoons by the heated pool. The open-concept living areas are designed for seamless indoor-outdoor living, with large windows capturing breathtaking water views. Ascend to the second floor to find the sophisticated primary ensuite, a true retreat featuring panoramic bay views, balcony access, and a spacious walk-in closet. Two additional guest rooms on this floor provide picturesque water views and share a well-appointed full bath, ensuring comfort and privacy for all. Boating enthusiasts will appreciate the private boat dock, offering convenient access to the bay and endless adventures on the water. Whether you're lounging by the pool, sunbathing on the private community beaches, entertaining on the balconies, or exploring the coastal waterways, this home promises an unparalleled lifestyle. Don’t miss out on the opportunity to own this exquisite bayfront sanctuary—schedule your private tour today and step into a world of luxury and tranquility!

43 Tarpon Road, E. Quogue

13 Cedarfield Lane, Westhampton
$3,850,000
5 Beds ⋅ 5 Baths ⋅ 1048453 MLS
Brand new construction showcasing timeless craftsmanship and abundant natural light, with 10-foot ceilings on the first floor, 9-foot on the second and wide plank white oak throughout. Extensive custom millwork includes picture molding in the foyer, a coffered office ceiling, wood beams in the kitchen, built-in mudroom cubbies with washer/dryer, a large Butler's Pantry and a custom primary bedroom Walk-In Closet. The chef’s kitchen features a La Cornue range, Sub-Zero refrigeration, Bosch appliances, custom cabinetry with wine storage, and a large center island, opening to a great room with a gas fireplace and custom built-ins. A fully integrated Control4 smart home system, Sonos whole-home audio, hardwired networking, and an extensive security camera system provide modern convenience and peace of mind. Spa-like baths with premium finishes complete the home's warm, cohesive design. Outdoors, enjoy a heated saltwater pool with automatic cover, professional landscaping, masonry, landscape lighting, and outdoor audio. A full outdoor kitchen and an approximately 16x28-foot pool house with its own kitchen and full bath make summer entertaining effortless. Set on just under an acre, the property also offers room to add a pickleball court, putting green, or other custom amenities.

13 Cedarfield Lane, Westhampton

300 Terry Path, Mattituck
$3,850,000
6 Beds ⋅ 4 Baths ⋅ 1019513 MLS
Tucked away along Terry Path, a rustic country lane within, an offshoot of the Camp Mineola Beach Association, this exceptional waterfront property is nestled in a quiet seaside enclave along the Great Peconic Bay. Opportunities to purchase within this historic neighborhood are exceptionally rare, making this a truly special offering. Set on approximately 1.4 acres with more than 110 feet of unobstructed frontage on the Great Peconic Bay, the classic Cape Cod-style residence offers timeless charm and tremendous potential. The spacious interior is centered around a striking stacked red brick wood-burning fireplace, while outside, a private sugar sand beach and full bulkhead provide an ideal setting for enjoying the waterfront. A substantial original boathouse, complemented by a newer three-car garage and expansive bonus space above, offers endless possibilities for storage, recreation, or future customization. The level, cleared grounds enjoy abundant sunlight throughout the day and provide ample space for expansion from the house, an in-ground pool as part of a remarkable waterfront compound. Combining a coveted Bayfront setting, generous acreage, and the enduring character of one of the North Fork's most treasured beach communities, this is a rare opportunity to create an exceptional coastal retreat.

300 Terry Path, Mattituck

1 Carver Street, Sag Harbor
$3,850,000
3 Beds ⋅ 3 Baths ⋅ 990791 MLS
Coastal Sophistication: Modern Masterpiece in Sag Harbor Village Perched at one of the village's highest points, 1 Carver Street is an architectural sanctuary designed for the sophisticated entertainer. This light-drenched contemporary balances gallery-style aesthetics with the vibrant, walkable energy of Sag Harbor Village. A soaring atrium with a custom white oak staircase connects two distinct wings. The two-story great room, framed by walls of glass and a sleek fireplace, creates a luminous backdrop for showcasing significant art. The chef's kitchen-featuring custom cabinetry and Viking/Fisher & Paykel appliances-flows effortlessly into the dining areas, making it a premier venue for hosting. Beyond the automated gated entrance lies a private paradise. A brand-new gunite pool and spa are surrounded by extensive professional landscaping, all brought to life at night by stunning architectural lighting. The covered rooftop deck offers built-in seating and panoramic, distant water views-the ultimate setting for sunset cocktails. Experience total seclusion and extreme convenience, just moments from the world-class dining and deep-water docks of Sag Harbor's historic center.

1 Carver Street, Sag Harbor

278 Hampton Street, Sag Harbor
$3,850,000
6 Beds ⋅ 7 Baths ⋅ 979851 MLS
Modern Elegance in Sag Harbor Village Discover an exquisite blend of traditional Hamptons elegance and modern craftsmanship in this beautiful new construction located in the renowned Sag Harbor Village and nearby beaches. This 4,500 sqft. brand-new custom home features six bedrooms on three thoughtfully designed levels. Nestled on a serene .30-acre lot, this architectural gem redefines Hamptons living. Step through the grand entrance into an ideal open layout, where soaring double-height ceilings and expansive glass windows and doors bathe the interiors in natural light. A uniquely designed staircase with glass railings makes a striking statement, seamlessly connecting the home’s thoughtfully designed levels. At the heart of the home, the stunning chef’s kitchen boasts Wolf appliances, a Sub-Zero fridge/freezer, and a Bosch dishwasher, complemented by quartz countertops. A separate butler’s pantry with a full-size sink, custom cabinetry, and additional prep space ensures effortless entertaining. The living room features a dramatic wood-burning fireplace with Calacatta marble, creating a warm yet refined ambiance. A wet bar with quartz countertops, and wine fridge enhances the space, perfect for hosting. French doors open to a lovely garden area, and a powder room and en-suite junior suite complete the first level. Retreat upstairs to the primary suite, an oasis of tranquility with vaulted ceilings, custom walk in closets, a stunning bathroom and a private balcony overlooking the pool. This level boasts two additional en-suite bedrooms with ultimate privacy and natural light. As you transition to the finished lower level, you will notice a design that is focused on both relaxation and recreation. Embracing a modern aesthetic; large format porcelain tiles and white marble span the entire floor. Witness two more generous bedrooms, two bathrooms, and an entertainment space with a gas fireplace. No stone was left unturned as this level is complete with a built-in entertainment bar with quartz countertops and wine cooler, as well as a versatile additional space that offers endless possibilities as a gym, office, or playroom with direct access to the yard and pool. Outside, an elegant covered veranda flows seamlessly into the heated Gunite pool, setting the stage for unforgettable gatherings. Designed for all-season enjoyment, this back yard boasts an electric fireplace, ceiling fans, and custom louvre shutters. A BBQ area enhances the outdoor dining experience, while an outdoor shower adds a touch of resort-style luxury. For added flexibility, an oversized detached garage could be converted to a pool house. As an added bonus, the property is equipped with four-zone heating and cooling, and a state-of-the-art security system with Google Nest cameras and thermostats. Do not miss your chance to experience the pinnacle of Hamptons living at this Sag Harbor Village retreat.

278 Hampton Street, Sag Harbor

8 Hilo Drive, Shelter Island
$3,850,000
4 Beds ⋅ 6 Baths ⋅ 962070 MLS
This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail, featuring an open floor plan with elegant white oak and porcelain tile flooring, stone countertops, and premium Thermador appliances throughout. Expansive living spaces are designed to embrace the surrounding views, while the second level covered deck offers the perfect setting for unwinding against a picturesque bay backdrop. Additional amenities include a heated gunite pool, radiant heat, wet bar, fireplace, pantry, and other thoughtful features that enhance everyday living. Ideally situated in Shelter Island, the property provides a peaceful retreat with convenient access to local amenities, beaches, and the area's natural beauty. Whether envisioned as a year-round residence or a serene getaway, this exceptional new construction presents a rare opportunity to enjoy modern luxury in a tranquil waterfront setting. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

8 Hilo Drive, Shelter Island

32 S Phillips Avenue, Speonk
$3,800,000
5 Beds ⋅ 6 Baths ⋅ 1036986 MLS
Experience elevated living in this exceptional new construction home, thoughtfully designed with luxurious finishes, impressive craftsmanship, modern energy-conscious features, and resort-style amenities. The sophisticated interior features 9-foot ceilings throughout the first floor, hydronic heating, central air conditioning, and beautifully appointed spaces designed for everyday comfort and entertaining. The gourmet kitchen showcases premium Thermador appliances, quartz countertops, propane gas cooking, and high-end Kohler fixtures throughout. Each bedroom is a private retreat with its own en-suite bathroom for privacy and comfort. The expansive full finished basement features impressive 10-foot ceilings and includes a gym, bedroom, full bathroom, and spacious living room, providing exceptional additional space for guests, recreation, and entertaining. A solar energy system adds to the home's modern appeal and energy-conscious design. Step outside to your own private resort. The professionally landscaped and fully fenced backyard features a spectacular 20' x 40' heated in-ground, gunite saltwater pool with spa, surrounded by beautiful pavers, creating an ideal setting for relaxing and entertaining. Underground sprinklers maintain the landscaped grounds, while an electronic gated entrance and private driveway add privacy and distinction. Propane fuels the gas cooking, fireplace, and pool heat, combining convenience with year-round comfort. From its sophisticated finishes and en-suite bedrooms to its impressive finished lower level and resort-style backyard, this lavish new construction delivers an outstanding combination of luxury, privacy, comfort, and modern living. Images are AI-generated for illustrative purposes only and are not drawn to scale or intended as an exact depiction of actual conditions.

32 S Phillips Avenue, Speonk

96 Godfrey Lane, Huntington
$3,799,999
4 Beds ⋅ 5 Baths ⋅ 917337 MLS
Discover a rare offering that blends modern luxury with spa-like serenity. This residence was designed to be both a retreat and a showpiece, combining high-end luxury finishes, seamless indoor-outdoor living, and tranquil natural surroundings. Walls of glass invite light and greenery into every room, creating a constant connection to nature. The open floor plan features a chef’s kitchen with professional-grade appliances, custom cabinetry, and expansive island seating—ideal for both entertaining and everyday living. Living and dining spaces flow effortlessly to outdoor patios, where landscaped gardens and serene seating areas extend the home’s livable footprint. The primary suite is a true sanctuary with floor-to-ceiling windows, spa-inspired bath with soaking tub and dual sided rainfall shower, with floor to ceiling windows overlooking lush grounds. Additional bedrooms offer the same level of comfort and style, ideal for guests or family. Every bathroom has been designed with European natural stone & micro-cement, luxury designer fixtures, and a focus on wellness and relaxation. Outdoors, curated landscaping and multiple gathering spaces set the stage for morning coffee, evening cocktails, or hosting under the stars. Enjoy a dip in the in-ground gunite, heated, saltwater pool surrounded by approximately 4,000 sq ft of patio space. Every corner of this property has been crafted to evoke calm, beauty, and a lifestyle of understated luxury. This is not just a home—it’s an escape, ready to be lived in and loved every day.

96 Godfrey Lane, Huntington

50 Sunset Avenue, E. Quogue
$3,799,000
4 Beds ⋅ 4 Baths ⋅ 1022922 MLS
Nestled along the waterfront in East Quogue, 50 Sunset Avenue offers the rare combination of a beautifully renovated, move-in-ready residence and exceptional future potential. Thoughtfully reimagined with an extensive 2026 renovation, this four-bedroom, four-bathroom home with a dedicated office and sauna provides refined coastal living today while offering the opportunity to expand or create a larger waterfront estate in the future. With approvals already in place for an 18' x 46' pool and patio, generous outdoor space, and a versatile waterfront setting, the property presents endless possibilities without compromising its turnkey appeal. Inside, a welcoming foyer with two coat closets leads to bright, thoughtfully designed living spaces. The custom kitchen features quartz countertops, white cabinetry, a large center island, a Sub-Zero refrigerator and wine refrigerator, Wolf gas range, Miele dishwasher, wet bar, and pantry, creating an ideal setting for both everyday living and entertaining. The adjacent dining room enjoys tranquil water views, while the spacious living room is anchored by a striking stone wood-burning fireplace. A private home office offers flexibility for today's lifestyle. The well-designed floor plan includes four bedrooms and four full bathrooms, including a spacious primary suite with an en-suite bath and an additional guest suite with its own private bath. Radiant heated floors extend throughout the kitchen, dining room, laundry room, and all four bathrooms, while a sauna provides the perfect place to unwind. Additional features include a laundry room, central vacuum system, one-car garage, Buderus boiler with baseboard heat, two 275-gallon oil tanks, & central air conditioning. A whole-house backup generator, serviced semiannually, provides added peace of mind, while a Sonos surround sound system enhances the home's entertainment capabilities. The exterior has been equally transformed with durable Hardie cement-board siding, a new driveway, covered front porch, brick patio, irrigation system supplied by well water, and a natural gas connection for the outdoor barbecue. The private dock offers exceptional flexibility for a variety of watercraft, including boats and jet skis, making it easy to enjoy life on the water. Whether enjoyed exactly as it stands or envisioned as the foundation for a future custom waterfront estate, 50 Sunset Avenue presents an exceptional opportunity to own a renovated waterfront property with both immediate enjoyment and long-term potential in one of East Quogue's most desirable settings. Pool photos are renderings.

50 Sunset Avenue, E. Quogue

1810 Main Road, Jamesport
$3,795,000
4 Beds ⋅ 4 Baths ⋅ 1027302 MLS
There are properties that offer more space, and then there are places that offer an entirely different way of living. Positioned in the heart of the North Fork, Starry Night Farms invites you to embrace a way of life that has become increasingly sought after yet is rarely found. Set on 6.3 exquisite acres, this remarkable equestrian estate is ideal for horse enthusiasts, hobby farmers, and those seeking an exceptionally private retreat. The charming yet updated farmhouse welcomes you with a classic covered wraparound porch, inviting interiors, and a bright rear sunroom overlooking the picturesque grounds, Outdoors, a heated saltwater pool, custom barbecue kitchen, and outdoor fireplace provide the perfect setting for entertaining family and friends. Designed with an equestrian lifestyle in mind, the property features two barns, indoor and outdoor riding arenas, ten horse stalls in total, and a dedicated tack room. Beyond its equestrian amenities, the property is filled with distinctive features, including a wine barrel sauna with steam and hot rocks, an art studio, putting green, and 16 raised garden beds ready for farm-to-table living. Apple, nectarine, cherry, and peach trees flourish throughout the backyard, while an established chicken coop with 20 chickens, productive Flow beehives, and multiple outbuildings offer exceptional flexibility. The grounds are further enhanced by a vineyard with thriving Merlot grapevines, creating an idyllic country setting where luxury and sustainable living come together. This one-of-a-kind Jamesport estate presents a rare opportunity to enjoy refined country living, premier equestrian facilities, and resort-style wellness amenities within one extraordinary property. Luxury is no longer defined simply by what you own, but by how you live.

1810 Main Road, Jamesport

5 Sea Gull Road, Shelter Island
$3,795,000
5 Beds ⋅ 5 Baths ⋅ 1016596 MLS
Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the relaxed waterfront lifestyle. Designed for both entertaining and everyday enjoyment, the property features two private docks ideal for boating, paddleboarding, and kayaking, along with a spacious waterside deck overlooking the sparkling water. The first floor has a large waterfront room that opens directly onto the deck, complemented by 4 generously sized bedrooms and 4 full bathrooms. Upstairs, soaring cathedral ceilings frame an open-concept great room encompassing the living, dining, and kitchen areas. Walls of glass capture stunning panoramic water views, creating a light-filled and inviting gathering space. Privately situated off the great room, the expansive primary suite offers a large walk-in closet and a spa-inspired bathroom. Completing the property is a detached 2-car garage with a finished upper level, providing the perfect space for recreation, a home office, artist’s studio, or additional guest accommodations. A rare opportunity to enjoy waterfront living with private docks, beach access, tennis, and some of Shelter Island’s most captivating water views.

5 Sea Gull Road, Shelter Island

11 Arbutus Lane, Stony Brook
$3,750,000
5 Beds ⋅ 6 Baths ⋅ 1050240 MLS
Welcome to “Westwinds,” one of the original and most iconic waterfront estates in Stony Brook Village. Privately set on 3.2 acres, this extraordinary property enjoys panoramic views of Stony Brook Harbor, West Meadow Creek, and Long Island Sound, with direct access to the water. Originally built in 1910, Westwinds retains many of its distinctive historic details while thoughtfully incorporating custom enhancements and continual upgrades that preserve and elevate its timeless beauty. The magnificent 1,428-square-foot Grand Ballroom, featuring soaring 11.5-foot ceilings, serves as the spectacular centerpiece of the home. Anchored by a dramatic fireplace and framed by unforgettable water views, the ballroom creates an exceptional setting for both grand entertaining and intimate gatherings. The main level is further enhanced by a spacious Chef’s Kitchen, custom-designed Dining Room, and inviting Sum Room. The second level has been thoughtfully redesigned to offer exceptional comfort and craftsmanship, featuring four en-suite bedrooms and an extraordinary Primary Suite complete with its own fireplace, luxurious spa bath, custom-designed closet, and dream office. Spectacular water views are enjoyed from virtually every room. Outside, the private waterside gunite pool and expansive patio have recently been restored, creating a remarkable setting for entertaining and enjoying the surrounding landscape. A newly constructed bulkhead secures more than 446 feet of waterfront, complemented by a private coastal walkway and direct water access. A truly rare opportunity to own one of Stony Brook Village’s most coveted waterfront properties, Westwinds is steeped in history as well as beauty. The estate was once the residence of Joe Simon, co-creator of Captain America, one of the most enduring superheroes in comic-book history. Every major mechanical system has been upgraded with high-quality, energy-efficient systems, providing modern comfort and reliability while preserving the character and elegance of this exceptional historic estate. Westwinds is a remarkable convergence of history, architecture, waterfront beauty, privacy, and convenience—an extraordinary estate in one of Long Island’s most treasured villages.

11 Arbutus Lane, Stony Brook

357 Smithtown Boulevard, Nesconset
$3,750,000
1049315 MLS
For the first time in more than 75 years, a legacy of land assembled over generations is being offered to the public. Beginning with the acquisition of its first parcel in 1949, what started as a single investment has evolved into a remarkable nine-parcel assemblage encompassing approximately 4.21 acres in the heart of the Ronkonkoma/Nesconset corridor. Never before offered as one acquisition, this is a once-in-a-generation opportunity to control an entire mixed-use portfolio with exceptional flexibility and long-term potential. More than just real estate, this is the opportunity to shape the future of an entire development block. Whether your vision is a thoughtfully planned residential community, a mixed-use redevelopment, an income-producing investment portfolio, or a phased development strategy, this offering provides a foundation that would be extraordinarily difficult to recreate in today's market. The assemblage includes: • Two commercially zoned parcels with prominent frontage and visibility along Smithtown Boulevard. • A six-unit multifamily property providing immediate income while future plans are developed. • Five contiguous residential development parcels totaling approximately 2.75 acres, offering exceptional potential for future residential expansion. • A single-family residence that may serve as rental property, or future redevelopment component. What makes this offering truly exceptional is not simply the acreage—it's the opportunity. Acquiring nearly an entire development block under one ownership eliminates the time, uncertainty, and expense of assembling multiple properties from different owners. It creates a level of flexibility and control that is increasingly difficult to find in today's market. Strategically positioned with frontage on Smithtown Boulevard and additional access from Spectacle Lake Drive and Lillian Drive, the property enjoys outstanding visibility, multiple access points, proximity to Lake Ronkonkoma, the Long Island Rail Road, shopping, dining, major transportation corridors, and regional employment centers. Very few opportunities offer this combination of location, existing income, commercial frontage, residential development potential, and long-term flexibility within a single acquisition. For more than seven decades, this property has been part of one family's story. Today, it is ready to become part of someone else's vision. All information is deemed reliable but not guaranteed. Buyers are responsible for independently verifying zoning, permitted uses, development potential, approvals, utilities, lot dimensions, environmental conditions, and all other matters material to their intended use.

357 Smithtown Boulevard, Nesconset

244 N Main Street, Southampton
$3,750,000
6 Beds ⋅ 7 Baths ⋅ 1035855 MLS
SOUTHAMPTON VILLAGE CHARM - IDEAL LOCATION, TIMELESS APPEAL Nestled in the heart of Southampton Village, this recently renovated colonial home seamlessly blends historic charm with modern convenience. Beyond being a stunning residence, this home offers a proven rental history, making it a compelling investment opportunity. Just minutes from the vibrant village center, this property captures the essence of Southampton living. With 6 bedrooms, 7 bathrooms, and a thoughtful layout, this residence is perfectly suited for luxurious living and entertaining. The main level features an inviting open floor plan, highlighted by multiple sunlit living spaces, a cozy fireplace, and a formal dining room. The fully-equipped chef's kitchen is a standout, boasting quartz countertops, a large center island, stainless steel appliances, and a commercial-grade gas stove. Adjacent to the kitchen, a serene sun-room surrounded by lush greenery offers an ideal space for an office or sitting area. The main-floor primary suite is a private retreat, featuring a separate sitting room, en-suite bathroom, and exclusive access to a charming patio adorned with bistro lights. Upstairs, five spacious bedrooms, each with updated en-suite baths, offer comfort and elegance for family and guests. Step outside to your backyard oasis, where relaxation awaits. A pergola-covered deck, stone patio, and sparkling in-ground pool are surrounded by mature landscaping, a picturesque English garden, and sculptural accents. Evenings can be spent gathered around the fire pit or enjoying outdoor activities in this thoughtfully designed space. A true turn-key village home with easy access to the Southampton train and Jitney. The driveway can accommodate up to 10 cars, with extra street parking available.

244 N Main Street, Southampton

357 Smithtown Boulevard, Nesconset
$3,750,000
3 Beds ⋅ 2 Baths ⋅ 1017932 MLS
For the first time in more than 75 years, a legacy of land assembled over generations is being offered to the public. Beginning with the acquisition of its first parcel in 1949, what started as a single investment has evolved into a remarkable nine-parcel assemblage encompassing approximately 4.21 acres in the heart of the Ronkonkoma/Nesconset corridor. Never before offered as one acquisition, this is a once-in-a-generation opportunity to control an entire mixed-use portfolio with exceptional flexibility and long-term potential. More than just real estate, this is the opportunity to shape the future of an entire development block. Whether your vision is a thoughtfully planned residential community, a mixed-use redevelopment, an income-producing investment portfolio, or a phased development strategy, this offering provides a foundation that would be extraordinarily difficult to recreate in today's market. The assemblage includes: • Two commercially zoned parcels with prominent frontage and visibility along Smithtown Boulevard. • A six-unit multifamily property providing immediate income while future plans are developed. • Five contiguous residential development parcels totaling approximately 2.75 acres, offering exceptional potential for future residential expansion. • A single-family residence that may serve as an owner-occupied home, rental property, or future redevelopment component. What makes this offering truly exceptional is not simply the acreage—it's the opportunity. Acquiring nearly an entire development block under one ownership eliminates the time, uncertainty, and expense of assembling multiple properties from different owners. It creates a level of flexibility and control that is increasingly difficult to find in today's market. Strategically positioned with frontage on Smithtown Boulevard and additional access from Spectacle Lake Drive and Lillian Drive, the property enjoys outstanding visibility, multiple access points, proximity to Lake Ronkonkoma, the Long Island Rail Road, shopping, dining, major transportation corridors, and regional employment centers. Very few opportunities offer this combination of location, existing income, commercial frontage, residential development potential, and long-term flexibility within a single acquisition. For more than seven decades, this property has been part of one family's story. Today, it is ready to become part of someone else's vision. All information is deemed reliable but not guaranteed. Buyers are responsible for independently verifying zoning, permitted uses, development potential, approvals, utilities, lot dimensions, environmental conditions, and all other matters material to their intended use.

357 Smithtown Boulevard, Nesconset

357 Smithtown Boulevard, Nesconset
$3,750,000
1018235 MLS
For the first time in more than 75 years, a legacy of land assembled over generations is being offered to the public. Beginning with the acquisition of its first parcel in 1949, what started as a single investment has evolved into a remarkable nine-parcel assemblage encompassing approximately 4.21 acres in the heart of the Ronkonkoma/Nesconset corridor. Never before offered as one acquisition, this is a once-in-a-generation opportunity to control an entire mixed-use portfolio with exceptional flexibility and long-term potential. More than just real estate, this is the opportunity to shape the future of an entire development block. Whether your vision is a thoughtfully planned residential community, a mixed-use redevelopment, an income-producing investment portfolio, or a phased development strategy, this offering provides a foundation that would be extraordinarily difficult to recreate in today's market. The assemblage includes: • Two commercially zoned parcels with prominent frontage and visibility along Smithtown Boulevard. • A six-unit multifamily property providing immediate income while future plans are developed. • Five contiguous residential development parcels totaling approximately 2.75 acres, offering exceptional potential for future residential expansion. • A single-family residence that may serve as rental property, or future redevelopment component. What makes this offering truly exceptional is not simply the acreage—it's the opportunity. Acquiring nearly an entire development block under one ownership eliminates the time, uncertainty, and expense of assembling multiple properties from different owners. It creates a level of flexibility and control that is increasingly difficult to find in today's market. Strategically positioned with frontage on Smithtown Boulevard and additional access from Spectacle Lake Drive and Lillian Drive, the property enjoys outstanding visibility, multiple access points, proximity to Lake Ronkonkoma, the Long Island Rail Road, shopping, dining, major transportation corridors, and regional employment centers. Very few opportunities offer this combination of location, existing income, commercial frontage, residential development potential, and long-term flexibility within a single acquisition. For more than seven decades, this property has been part of one family's story. Today, it is ready to become part of someone else's vision. All information is deemed reliable but not guaranteed. Buyers are responsible for independently verifying zoning, permitted uses, development potential, approvals, utilities, lot dimensions, environmental conditions, and all other matters material to their intended use.

357 Smithtown Boulevard, Nesconset

Mt. Sinai
$3,700,000
1031016 MLS
** RARE AUTO MEGA CENTER OPPORTUNITY ** One of Long Islands largest AUTOMOTIVE SERVICE & SALES MEGA MALL BUILDING available for Sale/Lease, containing multiple separate station(s) with AUTO BODY -TINTING -AUTO REPAIR(S) -AUTO PAINT SPRAYING & AUTO SALES. Property is GRANDFATHERED into its current ZONING position directly on one of Long Islands most heavily traveled EAST/WEST 5-LANE corridors, allowing your SIGNAGE to be viewed by OVER ~43,000 V.P.D. VEHICLES DAILY. Multiple OVERSIZED Signage staging points for unobstructed sight lines from entire highway. State Highway Dedicated TURNING LANE leading to building with ** (2) DUAL EGRESS OVERSIZED CURB CUTS** for easy customer access from highway. Included in sale is newly installed and permitted INTERIOR SPRAY BOOTH with new high efficiency lighting. Building has ** SIX (6) BAY DOORS, spaced into separate BUSINESS OPERATIONS CENTER(S), all remotely operated via door switches. Building has HIGH INTERIOR CEILINGS for lifts, allowing for TRUCK & LARGER VEHICLE service and Expansive, paved and level PARKING LOT for ~28 VEHICLES & SALES. Prime END-USER OPPORTUNITY for a one-stop, AUTOMOTIVE MECCA for talented Automobile Business Operators - or - (Medical/Retail) RE-DEVELOPMENT OPPORTUNITY, located on one of LONG ISLANDS PRIME COMMERCIAL & COMMUTER BUSINESS CORRIDORS (Call for Details) *** BRING YOUR BUSINESS HERE FOR 2026 ! ***

Mt. Sinai

550 Moriches Road, Head Of Harbor
$3,699,000
5 Beds ⋅ 8 Baths ⋅ 1037676 MLS
A Rare Opportunity to Create Your Custom Estate on Long Island Opportunities like this are exceptionally rare on Long Island. Set within one of the area’s most prestigious and private villages, this extraordinary new-construction estate offers the space, privacy and ability to customize that are increasingly difficult to find. Privately positioned on a breathtaking 2.35-acre wooded property with an additional one-acre private driveway, this impressive 7,000+ square-foot residence has been thoughtfully designed to combine timeless architecture with today’s most sought-after luxury amenities. Construction has progressed to the point where private tours can now be scheduled, while still offering the opportunity to personalize select finishes and make this remarkable home your own. A sweeping asphalt and stone driveway with cobblestone edging leads to the grand two-story traditional residence and oversized three-car garage. Inside, dramatic proportions immediately set the home apart, with a 20'6" two-story foyer and family room, 10-foot ceilings on the main level, a full 10-foot walk-out basement, and an elevator servicing all floors. The main level is designed for both everyday luxury and effortless entertaining. A spectacular chef’s kitchen features high-end Subzero separate refrigerator and freezer and Wolf appliances; subzero wine cabinetry and wet bar sub-zero, custom cabinetry with wood buildins, granite or quartz countertops, an expansive center island with prep sink, and radiant-heated porcelain floors. The soaring two-story family room is centered around a modern linear gas fireplace and coffered ceiling, while the formal dining room features custom built-ins and elegant millwork. A highly desirable **first-floor en suite** provides exceptional flexibility and convenience. The home also features a primary en suite wing along with 3 additional en-suite bedrooms, wide White Oak flooring, custom closet systems, radiant-heated floors, **two saunas and two steam showers**. Spa-inspired baths with premium Kohler fixtures complete the experience. Outdoor living is equally impressive. A covered rear porch with its own gas fireplace creates a beautiful setting for year-round entertaining, while a dedicated exterior-access full bathroom is ideal for a future pool. An in-ground pool is optional and may be customized to the buyer’s vision. The full 10-foot walk-out basement, complete with a full bathroom and outside entrance, offers tremendous possibilities for additional recreation, fitness, entertainment or guest space. Behind the beauty is equally impressive construction and infrastructure, including engineered wood-web floor joists, 400-amp electric service, natural gas, public water and seven oversized drywells. The home is also designed to accommodate a future generator and pool. Throughout the residence, wide White Oak hardwood floors, substantial moldings, custom millwork and an extra-wide staircase with open railings reflect the level of craftsmanship invested in every detail. More than a new home, this is an opportunity rarely available on Long Island: a newly built 7,000+ square-foot custom estate on exceptional acreage within an exclusive village — offering privacy, scale, luxury and the chance to make the finishing touches uniquely your own. *3D Reality Tours shown are examples of the builder’s previous work and are intended to demonstrate quality and craftsmanship; they do not depict this exact home.

550 Moriches Road, Head Of Harbor

1480 Old Wood Path, Southold
$3,695,000
3 Beds ⋅ 4 Baths ⋅ 997738 MLS
Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision. The grounds are equally compelling. A tennis court is already in place, and the oversized detached three-car garage adds flexibility for storage, studio space, or future accessory use, leaving ample room to site a pool. Centrally located with easy access to the North Fork’s vineyards, farm stands, restaurants, and marinas, the setting strikes a balance between privacy and convenience. Offerings with this combination of land, beach quality, and potential are increasingly rare, presenting a clear opportunity to create a premier waterfront compound.

1480 Old Wood Path, Southold

150 Deer Run, Southold
$3,675,000
5 Beds ⋅ 6 Baths ⋅ 1031351 MLS
Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany front door and decking, solid wood closet systems, bespoke pantry shelving, and a handmade stone mantle and hearth. This lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with Bertazzoni and Bosch appliances, extra large island and breakfast nook, formal dining room with Butler's pantry, first floor junior primary ensuite, and library. Upstairs is a spacious primary ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar, gym, additional bedrooms or other uses. Outside enjoy multiple covered porches and your lovely pool, all surrounded by the peace and quiet of this serene and private setting. This is truly a Hampton-style masterpiece on the North Fork.

150 Deer Run, Southold

608 Shore Drive, Oakdale
$3,650,000
5 Beds ⋅ 5 Baths ⋅ 1029824 MLS
SUMMERWIND – An Extraordinary Waterfront Estate on the Connetquot River. Welcome to Summerwind, one of Oakdale’s most distinguished waterfront estates. Privately set behind stone gates on 1.09 beautifully landscaped acres, this custom-built residence offers approximately 6,286 square feet of luxurious living space, 200 feet of Connetquot River frontage, and a 150-foot private deep-water dock with float and direct access to the Great South Bay, Fire Island, and the Atlantic Ocean. Built in 2004 with exceptional craftsmanship, this three-story brick Colonial showcases Brazilian cherry hardwood floors, handcrafted custom millwork including archways & crown moldings, soaring ceilings, crystal chandeliers, wall sconces and timeless architectural details throughout. The gourmet chef’s kitchen features custom cabinetry, expansive granite countertops, premium appliances, pantry with additional refrigerator, and an oversized center island that opens seamlessly to the spectacular Great Room with a coffered ceiling and fireplace. The luxurious primary suite offers a private sitting area with fireplace, spa-inspired bath, his/hers walk-in closet suite has custom dressing room and built-ins with inlaid custom doors and island with marble tops and lighting, laundry shoot from primary bedroom to laundry room and a private balcony overlooking the resort-style backyard and waterfront. Additional guest suites, a formal dining room, music room, executive office, billiards room, home theater, recreation rooms, tremendous amount of closets for storage, a finished 2000 square foot third floor, and a full finished basement with outside entrance provide exceptional space and flexibility, and the outdoor living rivals a private resort with a 48’x 28’ freeform Gunite pool featuring a natural rock waterfall and waterslide, a 10’x14’ pool cabana, expansive covered terraces, natural stone patios, fire pit, professionally landscaped gardens, and a private sports court. Western exposure provides breathtaking sunsets over the Connetquot River. Built to an exceptional standard, the home features 2x6 construction, 600-amp electrical service, 45kw whole-house diesel backup generator, security cameras and alarm, dual-fuel heating (natural gas and oil), six-zone high-efficiency air conditioning, radiant-heated bathroom floors, separate electrical subpanels throughout the home, garage, and cabana, and a 4-inch water service. Situated at an approximate elevation of 11.5 feet in an X Flood Zone, no FEMA flood insurance is currently required. Summerwind is a rare opportunity to own one of Long Island’s premier waterfront estates—where timeless architecture, exceptional engineering, world-class boating, and resort-style living come together in one extraordinary property. A legacy estate unlike any other.

608 Shore Drive, Oakdale

1999 Deerfield Road, Water Mill
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 1012206 MLS
Set on a beautifully landscaped shy 2 acres in one of Water Mill's most desirable locations, this "just renovated" residence offers a seamless blend of Hamptons architecture and modern luxury. Designed for effortless year-round living, the residence features gracious gathering spaces, a beautifully appointed chef’s kitchen and luxurious bedroom suites that provide comfort and privacy. Expansive windows and glass doors invite natural light while creating connection to the surrounding grounds. Mature landscaping frames a private retreat with ample space for relaxation, recreation and entertaining. Every element has been carefully curated to deliver a turnkey Hamptons lifestyle in a coveted Water Mill setting. Ideally located moments from ocean beaches, world-class golf, renowned farm stands, equestrian facilities and the villages of Southampton, Bridgehampton and Sag Harbor, 1999 Deerfield Road presents a rare opportunity to enjoy a fully renovated home in the heart of the Hamptons.

1999 Deerfield Road, Water Mill

18 Ocean Bay Boulevard, Ocean Bay Park
$3,600,000
5 Beds ⋅ 4 Baths ⋅ 1007104 MLS
Experience the best of Fire Island living in this newly constructed Ocean Bay Park home offering ocean views, bay views, and resort-style outdoor space. Designed for effortless summer living, this 5-bedroom, 4-bath retreat features bright open interiors, modern finishes, and seamless indoor-outdoor flow. Enjoy sunrise over the ocean, sunset over the bay, and long afternoons around your oversized heated pool. The expansive roof deck delivers panoramic views and the perfect setting for entertaining. A rare opportunity to own a turnkey luxury home under $4M in one of Fire Island’s most sought-after communities. Highlights: - Ocean views - Bay views - Huge heated pool - New construction - Roof deck - Under $4M - 5 bedrooms - 4 bathrooms

18 Ocean Bay Boulevard, Ocean Bay Park

35 Flamingo Avenue, Montauk
$3,599,900
4 Beds ⋅ 4 Baths ⋅ 982906 MLS
AKA-15 Edgemere Street. Elegant Montauk Retreat With Sunset Water Views. Privately set on an elevated acre, this immaculate traditional home offers sweeping sunset views over the Long Island Sound and the perfect balance of privacy and proximity to Montauk's beaches and Village. Spanning approximately 2,400 square feet, the home features four bedrooms and four full baths, with beautifully appointed living spaces, dark hardwood floors, and custom finishes throughout. The open-concept layout includes a spacious eat-in kitchen with a large center island and dining nook, flowing seamlessly into a light-filled living room with fireplace and access to the outdoor patio and hot tub. Designed for both relaxation and entertaining, the property offers expansive outdoor space with room for a pool, making it an exceptional opportunity to further enhance value. Located just moments from Navy Beach, Ditch Plains, and Montauk’s vibrant dining scene, this turnkey home presents a rare opportunity to own a private retreat with water views in one of the Hamptons’ most sought-after destinations.

35 Flamingo Avenue, Montauk

431 Dune Road, Westhampton Beach
$3,599,000
4 Beds ⋅ 4 Baths ⋅ 1035758 MLS
Location Location! Rare Dune Road Oceanfront Retreat! Experience the ultimate Hamptons lifestyle at 431 Dune Rd in Westhampton Beach. This breathtaking, contemporary, oceanfront home features 4 spacious bedrooms and 4 full bathrooms, each offering a private balcony with panoramic, unobstructed ocean views. The bright, open concept living area boasts soaring vaulted ceilings, floor-to-ceiling windows, and a cozy wood-burning fireplace. Enjoy seamless outdoor living, on the expansive ocean facing deck, ideal for entertaining, alfresco dining, or taking in the sea breeze. Complete with a primary suite fireplace, Moriches Bay access nearby, and located just a short distance from Westhampton Beach Village's top dining and shopping. Don't miss this incredible oceanfront opportunity!

431 Dune Road, Westhampton Beach

170 S Penataquit Avenue, Bay Shore
$3,599,000
3 Beds ⋅ 3 Baths ⋅ 1032772 MLS
SPECTACULAR 2.75-ACRE WATERFRONT CONTEMPORARY ESTATE A truly rare opportunity to own an extraordinary privately gated 3,800 sq. ft. waterfront estate set on 2.75 breathtaking acres with over 1,000 feet of bulkhead and spectacular water views. Step through the grand double glass doors into a stunning open-concept interior featuring soaring windows, beautiful ceramic flooring, and a magnificent chandelier overlooking the water. The home offers 3 bedrooms, 3 bathrooms, a second-floor loft, dining room, living room with fireplace, and a 3-car garage.The fabulous chef’s kitchen features custom wood cabinetry, a large granite island, and professional Wolf and Verona stainless-steel appliances. The luxurious primary en-suite offers a spa bath, walk-in closet, glass doors with balcony and deck with bay views, elevator access, along with a convenient second-floor laundry room. The waterfront lifestyle is truly exceptional, offering over 1,000 feet of bulkhead, a large boat slip accommodating two 65-foot yachts, a boat ramp, and a dedicated cut-out for multiple jet skis. A spacious boathouse and waterfront gazebo provide the perfect setting for enjoying the water, while a beautiful patio and pergola create an ideal space for outdoor entertaining and relaxation. Take in breathtaking sunsets with picturesque views of the Robert Moses Bridge. Additional amenities include a full-house generator, 27-zone sprinkler system, and an on-demand tankless hot water heater. Perfectly positioned approximately 60 minutes by LIRR to NYC for world-class dining, entertainment and shows, and approximately 60 minutes to the Hamptons and its renowned wineries. From your own home or the nearby local ferries, enjoy a quick 20 minute ride to Fire Island's Ocean Beach and other sought after destinations, where you can spend the day exploring charming shops, enjoying waterfront dining and live music, or relaxing on the beautiful white sand beaches. It's the perfect blend of waterfront living, convenience, and the quintessential Fire Island lifestyle. Conveniently located near shopping, transportation and everyday amenities. A magnificent waterfront estate. An extraordinary lifestyle. A rare opportunity. Call today for your private showing.

170 S Penataquit Avenue, Bay Shore

556 Dune Road, Westhampton
$3,599,000
4 Beds ⋅ 4 Baths ⋅ 1024503 MLS
Let this be your perfect Hampton beach home! Boasting panoramic views and natural flora, this destination home will be where you want to be ....always! Meticulously as well as beautifully maintained, it has been refreshed with all weather siding, decking along with all windows and doors replaced. The home benefits from highly efficient solar panels worth bragging about. 556 Dune Road warmly welcomes you with well tended gardens and flowering pathways. Entering the home's interior space, a sense of calm comes over you via the endless water views about the living room, dining area and remodeled kitchen. A first floor en suite is generous in size also offering grand views of the surrounding water front. Three additional bedrooms are on the 2nd floor, each offering ample space and sunlight. The rear deck, an extension of the home's inviting interior space, is ideal for entertaining, fitted with outdoor speakers. There is a convenient gated entrance to the home's heated pool and lounging area enhanced by lush, colorful flower boxes. Accessible directly behind the home is a private walkway leading to your own bay beach. Most convenient is the right of way to the ocean only a stone's throw away. A manicured island about the home's circular driveway, offers ample space for all those who will want to come for a stay. This home is a must see and experience the true vibe of Hampton living on Dune.

556 Dune Road, Westhampton

2 D'Amico Court, Melville
$3,598,000
5 Beds ⋅ 6 Baths ⋅ 1032791 MLS
Welcome to Melville’s Newest Exclusive Development. A Private Cul-de-Sac Featuring Just Three New Luxury Homes and Ultimate Privacy. Offering Over 6,000 Square Feet of Meticulously Designed Living Space, This Exceptional Residence Blends Luxury, Comfort, and Functionality. The First Floor Welcomes You With an Open Foyer and a Fluid Floor Plan, Featuring a Beautifully Appointed Kitchen With Viking Professional Appliances, That Flows Seamlessly Into the Breakfast Area and TV Room. A Formal Living Room and Dining Room Are Connected by a Butler’s Pantry, Creating the Perfect Setting for Entertaining. Enjoy Convenient Access From the Driveway Into the Mudroom, Along With a First-Floor En-Suite Bedroom Ideal for Guests. The Second Floor Features Four Spacious Bedrooms, Including an Impressive Primary Suite With His and Her Closets and a Luxurious Spa-Inspired Bathroom Complete With a Steam Shower. Full Laundry Room Conveniently Located Upstairs. The Finished Lower Level Provides Additional Space for Recreation, Entertaining, a Home Gym, or More. Step Outside to Lush Landscaping and a Blank Canvas Ready to Become the Private Backyard Oasis of Your Dreams. With Over an Acre of Unparalleled Privacy, This Exceptional Property Is a Truly Rare Offering. Opportunities Like This Do Not Come Along Often. Don’t Miss Your Chance to Make It Yours!

2 D'Amico Court, Melville

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.

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