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$2,700,000
3 Beds ⋅ 3 Baths ⋅ 995366 MLS
A Rare Opportunity!!! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long Island. The home itself offers a sun-filled living room with a fireplace and dining area, both featuring floor to ceiling windows which show off the magnificent seascape. The home also hosts an eat-in-kitchen, 3 bedrooms, 3 baths, a large basement, an oversized 2 car garage, and a large deck to enjoy the breathtaking scenery. If being on the water is for you, you've arrived. Don't miss this one time opportunity.

100 Sound Drive, Greenport
$16,999,000
7 Beds ⋅ 7 Baths ⋅ 886217 MLS
Set along the coveted shores of Dune Road in Quogue, this extraordinary oceanfront estate spans 1.4 acres of pristine coastal property, offering a rare blend of relaxed elegance and modern refinement. Thoughtfully renovated, the residence is designed to capture the essence of effortless Hamptons living with seamless indoor-outdoor flow and breathtaking views of the Atlantic Ocean. At the heart of the home, an expansive deck just off the kitchen creates the ultimate setting for al fresco dining and entertaining, where ocean breezes and panoramic vistas elevate every moment. The first floor is anchored by a luxurious primary suite, complete with a private walkway leading to an upper deck overlooking the Atlantic—your own serene retreat above the shoreline. This level also features a welcoming den with a wood-burning fireplace, along with three generously sized bedrooms and two full baths, all thoughtfully designed for comfort and style. The lower level provides an ideal space for guests, offering an ensuite bedroom, two additional bedrooms, a full bath, and a second den—perfect for relaxed gatherings or extended stays. Outdoors, the property transforms into a true summer oasis. A newly renovated heated gunite pool is perfectly positioned between the main residence and an amenity-rich pool house, creating a private resort-like setting. After a day at the beach, unwind poolside or retreat to the pool house, which features a spacious den, changing rooms, a kitchenette, and two full baths.Completing this exceptional offering is a private putting green, adding yet another layer of leisure to this remarkable coastal escape. A rare opportunity to own a premier oceanfront estate in one of the Hamptons’ most sought-after locations—where luxury, tranquility, and timeless coastal beauty converge.

40 Dune Road, Quogue
$2,295,000
6 Beds ⋅ 5 Baths ⋅ 994017 MLS
Experience the ultimate in coastal living with this extraordinary waterfront compound, privately nestled in the sought-after Holiday Beach community. This rare offering features a spacious main residence, a fully renovated guest cottage, plus a 56 Foot Harbor Master Boat which can be used to generate an AirBnb income and has two bedrooms, two bathrooms a kitchen and so much more! The main house welcomes you with a flowing layout that includes a dramatic great room, formal living room, elegant dining area, and a bright eat-in kitchen. The expansive primary bedroom boasts its own private terrace with stunning water views, while two additional bedrooms, a dedicated home office with its own bathroom, 2.5 more baths, and a full laundry room complete the interior. Step outside onto multiple levels of decks that offer panoramic views and unforgettable sunrises over the water. The guest cottage is a retreat in itself, beautifully renovated with vaulted ceilings and sophisticated finishes. It features a large ensuite primary bedroom with a generously sized walk-in closet, a versatile second bedroom/loft, and an open-concept family room with a cozy fireplace and dining area. The high-end eat-in kitchen is a chef’s dream, outfitted with sleek stone countertops, custom Ciuffo cabinetry, and premium stainless steel appliances. The cottage also includes its own laundry area and private garage. Outdoor living is just as impressive, with a stylish cabana with shower, a cold plunge pool or tub, and expansive decking that invites relaxation and entertaining. A deepwater dock extends 150 feet and includes water and electric, offering easy access to the inlet and bay for boating enthusiasts. Additional features include ductless air conditioning, central vacuum system, and deeded beach rights to Holiday Beach. Located just minutes from the Hamptons, this exceptional property provides easy access to world-class shopping, dining, and pristine beaches, all while offering the privacy and tranquility of a waterfront sanctuary. Call today for a private showing.

53 Old Neck Road S, Center Moriches
$2,175,000
4 Beds ⋅ 3 Baths ⋅ 993695 MLS
Bally Blue Haven | A Charming Waterfront Cottage in the Heart of Bellport Village Nestled in the picturesque Village of Bellport, this timeless waterfront cottage offers the perfect blend of classic charm and coastal living. With sweeping views of Bellport Bay, the home is surrounded by gardens and features multiple sleeping porches and direct beachfront access—an ideal setting for summer memories. The spacious interior includes 4-bedrooms and 3-baths, large living room, dining room and multiple bonus spaces, providing ample room for relaxing or entertaining. Whether you're enjoying a quiet morning on the porch or hosting guests for a sunset gathering, the layout offers comfort and flexibility. As a resident of Bellport Village, you will enjoy access to the Bellport Country Club, Mother's Beach and Ho-Hum Beach via village ferry. The property includes a detached 2-car garage and back patio and offers endless potential for updates. A rare opportunity to own a true village gem with unparalleled views and access—don’t miss this one-of-a-kind retreat.

4 Shore Road, Bellport Village
$1,425,000
3 Beds ⋅ 2 Baths ⋅ 993305 MLS
Charming 1879 Farmhouse with Waterfront Opportunity Set across 2 acres in Wading River, this beautifully preserved 1879 farmhouse offers a rare pairing of historic character and coastal lifestyle. The residence sits on .95 acres, complemented by a separate 1-acre Soundfront parcel with beach access and breathtaking views, completing this exceptional offering. Timeless details define the home, including a warm and inviting living room with wood-burning fireplace and custom built-ins. A thoughtfully designed 2012 addition introduces an open-concept kitchen, dining area, and sunlit den, creating a natural gathering space for both everyday living and entertaining. Wrapped in windows, the enclosed sunroom is a serene, light-filled retreat that invites quiet mornings, afternoon reading, or simply taking in the beauty of the surrounding property throughout the seasons, sure to become a favorite. The home offers 3 bedrooms and abundant natural light throughout. A detached 2-car garage is complemented by a versatile studio above, where a large picture window captures views of the Sound, ideal for an artist’s retreat or home office. A rare blend of historic charm, modern comfort, and coastal lifestyle.

2850 & 2856 N Wading River Road, Wading River
$400,000
992745 MLS
Fantastic opportunity to build your desired Commercial Enterprise or Residence on this Rare, Riverfront, Commercial-zoned 1.5 Acre Parcel! Possible Subdivision. Dream big and bold with your ideas and vision! Potential opportunities may be a Multi-Family dwelling, Country Bed and Breakfast, Deli or Restaurant, or Waterfront Recreational endeavor, (kayaking, canoeing, paddleboarding), the options are many, and you just need to bring your plans to the Town for approval. The scenic, Peconic River is right out your backyard, for many riverfront sporting pleasures, and the Peconic Riverfront Pedestrian Walk is only moments away, where you may enjoy the pedestrian boardwalk and public parkspace to unwind and relax, at any time during the day. The location is ideal, within close proximity to downtown Riverhead, with its plentiful stores, restaurants, offices, and medical facilities, as well as to the ever-popular Tanger Outlets, to ensure your shopping pleasure! This location is a Gateway to both the Hamptons and the North Fork, further enhancing its appeal. Must See!

1011-1021 W Main Street, Riverhead
$1,195,000
3 Beds ⋅ 2 Baths ⋅ 992997 MLS
Fabulous Sunsets from All Rooms Including Expansive 92-Foot Private Deck. Located 2 Minutes from Beach & Perched on a Hill on Quiet Cul-De-Sac Street. The Main Level Features Spacious LR & FDR w/Impressive Wall of Windows, Sliding Andersen Doors to 92 Ft Deck & Hot Tub, Beautiful Vaulted Ceilings, and Anchored by a Dramatic Stone Fireplace. Modern Eat-in Chefs Kitchen with a Large Granite Island. Spacious 3 Bedrooms, Den /Office, 2 Full Baths (& Jacuzzi). Spacious Lower (Walk Out) Level with Very High Ceilings & Windows, Laundry, & Access to 2 Car Garage & Long Private Driveway. Many Upgrades Include Radiant Heated Floors, Central Vac & Central Air Conditioning. Best Location and Beach 2 Minutes Away, Vineyards, Boating, Golf, and the Best of the North Fork and Hamptons Lifestyle!

10 Silver Beech Lane, Calverton
$1,495,000
5 Beds ⋅ 4 Baths ⋅ 992605 MLS
Wake up each morning to sweeping, unobstructed water views and the quiet rhythm of coastal living at 160 Sequams Lane W—an exceptional waterfront offering in the heart of West Islip. Perfectly positioned between a serene protected cove and the open waters of the Great South Bay, this rare property delivers a lifestyle defined by both tranquility and adventure. Set on a prominent corner parcel with an impressive 215 feet of Marine-LOC bulkheading, this expansive 5-bedroom, 3.5-bath Colonial presents a truly unique opportunity to create a custom waterfront estate. Whether you envision a sophisticated renovation or a ground-up architectural masterpiece, the setting alone provides a foundation that is nearly impossible to replicate. Inside, a flowing open-concept layout welcomes you with generous living spaces designed for both entertaining and everyday comfort. The chef’s eat-in kitchen is appointed with granite countertops, a center island, and ample cabinetry, seamlessly connecting to a sunlit family room anchored by a wood-burning fireplace. A formal dining room offers the perfect setting for elegant gatherings, while the formal living room—with its own gas fireplace—provides a refined space to unwind. Upstairs and throughout, five well-proportioned bedrooms offer flexibility for extended family, guests, or home office configurations. A separate entrance presents the opportunity for private guest quarters or a true accessory suite, ideal for multigenerational living or added versatility. Outdoors, the property becomes a waterfront dream—boat dock ready, with immediate access from your canal to the open bay in moments. Spend your days boating, paddleboarding, or simply enjoying panoramic sunsets over the water. With its rare dual-water exposure, the home captures both the calm of protected waters and the grandeur of wide-open bay views. Located just moments from the shops, dining, and charm of Babylon Village, this home offers the perfect balance of privacy and convenience—bringing together coastal luxury and vibrant village living. A truly exceptional offering with unlimited potential—this is where your waterfront vision becomes reality.

160 Sequams Lane W, West Islip
$699,998
4 Beds ⋅ 3 Baths ⋅ 991204 MLS
BACK ON THE MARKET!!! Circa 1855, the Captain Lewis Tooker Home sits prominently in Port Jefferson Village, offering historic charm with thoughtful modern updates. Designed by architect Geysea Sarkkany, this residence features a chef’s kitchen equipped with a 6-burner Viking stove, cabinetry, and a center island, oversized walk-in pantry. Just off the kitchen is a large formal dining room, two formal living rooms with gas fireplace, and a flexible layout offering 3–4 bedrooms, including an office or optional fourth bedroom. Third floor Scenic views of Port Jefferson Harbor. Recent improvements include heating system upgrades with a new radiator and rebalanced lines for improved efficiency, concrete repairs to the rear chimney, and the addition of a gas line for a fireplace insert. Exterior updates include a widened driveway with new blacktop/Belgian block border, white PVC fencing with gate, and additional wood picket fencing along the side and rear. The home has been newly sided, and the roof is approximately 15 years old. Additional features include central air conditioning, separate hot water heater, a detached two-car garage and back yard patio. 2 blocks from shopping and events in Port Jefferson Village, residents enjoy access to village beaches, country club amenities, live music, seasonal festivals. TAX GRIEVANCE FILED

108 High Street, Port Jefferson
$949,000
3 Beds ⋅ 2 Baths ⋅ 987905 MLS
Welcome to your quintessential North Fork coastal retreat! Tucked away on a quiet, tree-lined street with peek-a-boo water views, just moments from pristine beaches and world-class vineyards, this 3-bedroom, 2-bath beach house blends relaxed vacation vibes with everyday comfort. The property has a new roof, new gas water heater and a bright, open-concept main floor featuring a cozy fireplace for breezy evenings, and a seamless flow for entertaining. Your updated chef's kitchen comes fully equipped with brand new Stainless Steel appliances, new refrigerator, dishwasher, range/oven and microwave. The serene primary suite boasts a private marble en-suite bath, while two additional bedrooms offer plenty of room for family, friends, or a remote workspace. The spacious basement has bonus areas for recreation, movies, games, and storage. This lovely retreat also offers plenty of room for your vehicles and toys as it has a heated-attached large spacious 2 car garage, and a separate single car garage. Step outside into your own private oasis with mature landscaping, a spacious patio, and plenty of room to add a custom swimming pool. You also have exclusive access to a resident-only private beach on the Mattituck Inlet, perfect for enjoying peaceful water views, kayaking, water sports, and sunset picnics. This charming home is a short walk to the marina, restaurant, bar, and live entertainment. Moreover, Mattituck’s own “Love Lane” is only a short walk or bike ride to enjoy some of the best the East End has to offer. Surrounded by the best local farm stands, shops, wineries and 5 minutes away from multiple marinas and beaches, this property is the ultimate North Fork escape—whether you are seeking a seasonal vacation getaway, an investment opportunity, or your forever home.

680 Westview Drive, Mattituck
$2,375,000
987619 MLS
Rare 17.4-Acre Estate in Orient, NY With a 2.5 Acre & 3 acre single and separate residential building lots separated by 11.9 acres of development rights sold land. This exceptional property offers a unique opportunity to own a versatile, three-part estate in the coveted hamlet of Orient, NY, boasting approximately 20,209 square feet of interior space across multiple structures. Situated in a picturesque North Fork setting, the estate perfectly blends agricultural functionality, equestrian potential, and two opportunities to build a new residence on the 3 acre parcel and/or build a new residence on the 2.5 acre lot or convert an existing 4,578 sq. ft. barn to a residence, with existing architectural plans. Parcel 1 (2.5 Acres – Residential Use) The property's entrance on the main road leads into a thoughtfully arranged 2.5-acre parcel featuring four distinctive buildings. This parcel is also setback form the Main Road by approximately 250 feet. • 1,485 sq. ft. Storage Building: • 4,578 sq. ft. Multi-Use Building: Recently renovated, featuring new Anderson doors and windows, framed interior ready for customization, and a spacious second-floor loft spanning the building’s full width with architectural plans in place to convert to a residence I• 5,015 sq. ft. Concrete Block Storage Building: Impressively designed with 25-foot cathedral ceilings, metal shelving, and a durable concrete slab floor for heavy-duty storage. • A Quaint Cottage Storage Building Parcel 2 (11.9 Acres – Development Rights Sold) Dedicated to equestrian excellence, this fully fenced and tree-lined 11.9-acre area includes: • 6,615 sq. ft. Former Indoor Riding Arena: With expansive 30-foot ceilings, suitable for equestrian training or adaptable for various agricultural uses. • 5,015 sq. ft. Stable Facility: Professionally designed with 20 spacious horse stalls. • Four Paddocks and Riding Area: Enhancing the property’s equestrian appeal with ample space for grazing, riding, and training horses. Parcel 3 (3 Acres – Residential Building Lot) Elevated above the property, this picturesque 3-acre residential lot offers panoramic views over the equestrian estate and stunning vistas of the Long Island Sound. The perfect canvas for a home or a private estate compound. The property is located less than a mile from Narrow River Marina, a perfect destination to keep a powerboat or a sailboat. In addition, there is access to Hallock Bay and Hallock Bay Beach. Additional Features & Potential Uses Electricity services each building, supplemented by generators to ensure uninterrupted lighting and water supply. Beyond equestrian pursuits, this property's potential spans broadly across agricultural uses—including vineyards, cattle farming, organic produce, or other livestock operations. The expansive layout ensures flexibility to match your vision and lifestyle. This Orient property is truly a rare find, combining extensive acreage, practical infrastructure, stunning views, and unlimited possibilities. A prestigious offering on the North Fork—ready to become your ideal agricultural and multi-residential sanctuary.

29525 Main, Orient
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 973460 MLS
Build your dream home on this exceptional waterfront lot offering unobstructed, forever views and breathtaking sunsets over the pristine waters of the sound. With plans already in place, you can break ground on your custom home without delay. Nestled in one of the most sought-after locations on the North Fork, this property offers the perfect blend of privacy and convenience—just minutes from local vineyards, farm stands, dining, beaches, and marinas. Set in a serene and scenic location, this property offers direct access to miles of beach for peaceful walks along the shore, and is just moments from the tranquil Goldsmith Inlet, perfect for kayaking, paddleboarding, or simply enjoying nature at its finest. Whether you’re looking for a peaceful weekend retreat or a full-time coastal haven, this rare opportunity delivers it all. A one-of-a-kind acre-and-a-half property situated on a 40-foot-high bluff above the Long Island Sound, with clear views of the Connecticut shoreline and gorgeous northwest sunsets! Hidden off North Road (County Road 48) in Peconic, access is via a mile-long private road. This is the final piece of a six-lot subdivision. Delivering a powerful feeling of privacy, in a totally natural setting! Truly a MUST SEE for the individual searching for solitude, privacy, and relaxation! Full Building Permits Approved. Price listed is for vacant lot only including permits to build, which can be modified. Come see this extraordinary location and design your dream home!

4760 Blue Horizon Bluffs, Peconic
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 900582 MLS
Two acres of waterfront with beach, ramp and bulkhead.Mediterranean Style home, beautifully situated on Carlls River. Guest Cottage and garden shed with sliders patio and water view. (works for car collector storage too) Gracious home boasting beautiful botanical gardens and landscaping. Designer kitchen and bathrooms, custom cabinetry, and woodwork abounds. Hand painted Turret stairway to Juliet balcony overlooking living room, and 2 additional bedrooms, one with Balcony to Sunset views. Trees and gardens create idyllic setting. Inviting guest cottage with full bath and wrap around decks taking advantage of 203' waterfront with sandy beach. The potting shed can also be repurposed as car storage for the car collector, and kept as is for the avid gardener, boater or fisherman.

50 Cedar Lane, Babylon
$3,250,000
5 Beds ⋅ 4 Baths ⋅ 985525 MLS
206 Broadway, Saltaire — an exquisite, custom-crafted residence offering an elevated interpretation of coastal living. Poised on a rare six-lot parcel, this legacy property is placed perfectly equidistant from the bay and the main ocean beach. This 3,050 SF year-round sanctuary presents five bedrooms and three-and-a-half baths, composed with the clarity and refinement of a bespoke estate. The principal suite is a study in luxury: custom built-ins, hand-crafted millwork, a spa-like bath with soaking tub, glass-enclosed tile shower, dual towel warmers and radiant heated floors. A secondary ensuite on the second level enjoys private outdoor access via its own deck. Three newly renovated guest bedrooms and a dedicated office support both extended visits and everyday living. At the heart of the home, the chef’s kitchen harmonizes form and function — Sub-Zero refrigeration, Wolf appliances, reclaimed antique heart-pine countertops and radiant heat underfoot. An ancillary outdoor shed/pantry, equipped with a refrigerator and commercial freezer, makes entertaining effortless. The adjacent living and dining rooms, anchored by a wood-burning fireplace, built-in cabinetry and new wood floors, form an elegant setting for gatherings through every season. Seamless indoor-outdoor living is realized through an expansive main deck plus a screened porch designed for year-round use with discrete heating and air conditioning. Outdoor culinary amenities include a professional kitchen complete with Lynx Grill, quartzite counters, wood trellis, integrated planters, Sonos sound and a substantial shade canopy — a refined setting for hosting beneath the coastal sky. An above-ground basement of approximately 1,800 SF provides adaptable space for a gym, recreation suite or abundant storage, underscoring the home’s practical versatility. Throughout, finishes and systems have been curated to exacting standards: radiant heat in primary living areas and baths, robust mechanical systems and efficient climate control ensure comfort and reliability. With a dedicated office and durable materials, 206 Broadway functions as a true four-season residence. This is a once in a lifetime opportunity to acquire a meticulously realized home with access to Saltaire’s storied lifestyle — yacht club, tennis courts, sailing and village life.

206 Broadway, Saltaire
$1,459,000
3 Beds ⋅ 2 Baths ⋅ 983029 MLS
Water view meticulously renovated 3 bedroom 2-bath corner home in Greenport, offering privacy with a landscaped fenced-in garden. A true sanctuary, a large side open spacious garden with mature trees and an intimate private patio that overlooks the picturesque Sterling Harbor, alive with sailboats and fishing vessels. This thoughtfully renovated home has been thoroughly rebuilt, showcasing its architectural charm including pine flooring and a classic front porch. The lower level boasts an open-concept kitchen and living area, complemented by a sun-drenched room with water views, separated by pocket doors, ideal for a formal dining room or a versatile third bedroom. A full bath on this level adds convenience. Upstairs, you'll find two comfortable bedrooms and a dedicated small office area, all overlooking the serene rear garden and harbor. A second full bath completes the upper floor. There is also a full attic and a separate one car garage that is ideal for a possible future accessory housing unit and/or a great workshop equipped with its own 100 amp electric service. A pool or a rear extension are both possible options for a future owner. An Easy walk to the Greenport Village, or 15 minute walk to the Peconic Bay Manhasset Beach or to the LI Sound 67 steps Beach.

412 Atlantic Avenue, Greenport
$329,000
2 Beds ⋅ 2 Baths ⋅ 984696 MLS
Welcome to Glenwood Village - a 55 & Over Community Offering a 49 Year Lease starting at $800 per month. This Ranch Style Home features One Level Living at its finest! 2 Lovely Appointed Bedrooms and 2 Baths - Open Kitchen, Dining & Living Room Area - Laundry Room is Located off the Kitchen and makes its way out to A Covered Deck Overlooking a Pond. Carport, CAC, Shed & Spinkler System. Community Offers an Outdoor Park, Swimming Pool, Clubhouse with a State of the Art Gym, Library, Billiard Pool Room, Dance Hall & Full-Size Kitchen.

1661 Old Country Road Unit #417, Riverhead
$199,000
984552 MLS
Build your waterfront home on the scenic Peconic River. Located in (RFC) Riverfront Corridor. Lots of privacy. Many options and possibilities on this spectacular .60 acre lot.

1217 W Main Street, Riverhead
$1,745,000
3 Beds ⋅ 3 Baths ⋅ 982422 MLS
Welcome to the sleepy hamlet of Laurel on the edges of Jamesport and Mattituck! Deeded Beach! This craftsman style custom designed and built Hamptons style classic is everything you're hoping for! Beautiful and thoughtful detail throughout this fine home. Ten-foot ceilings, hardwood floors, crown mouldings, an outdoor shower and a fantastic screened in porch just off of the great room for 3 season enjoyment. Experience Nature at your doorstep with pond views. Very close to 2 gorgeous bay beaches. Veteran's Park is very close by with bay beach access and playground . Lovely great room with center island kitchen and open floor plan with wood burning fireplace! Elegant primary bedroom with upper deck for outdoor open-air privacy, with state-of-the-art en suite bath. Additional bedroom and bath and 2 designated office library spaces. Main level bedroom with full bath. Full basement and attached 2 car garage. This home is in like new condition and ready for the discerning buyer. Come and see for yourself and be pleasantly surprised!!! Enjoy all the North Fork offers, vineyards, craft breweries, beaches, boating, and many farm to table restaurants, farms and farmstands and golf courses!

360 Masters Road, Laurel
$2,475,000
4 Beds ⋅ 5 Baths ⋅ 981805 MLS
Living on The Links: Welcome to 350 Laurel Way, a spectacular residence in the coveted Laurel Links community, perfectly positioned along the second hole of this world-renowned links style golf course. This thoughtfully redesigned and fully updated home offers sun-drenched living spaces thanks to floor-to-ceiling windows in the great room, anchored by a dramatic stacked-stone fireplace. The layout blends sophistication and comfort, with seamless indoor-outdoor living. For the culinary enthusiast, the custom kitchen is a true centerpiece—featuring Decor appliances, an oversized island, a butler’s pantry, and a built-in banquette overlooking a chic pergola-covered deck. The main-floor primary suite is a private sanctuary with French doors opening to a bluestone patio, dual walk-in closets with custom built-ins, and a spa-inspired bathroom boasting three vanities, a soaking tub, and a walk-in shower with striking tile-work. Each of the three additional bedrooms is complete with its own en-suite bath, ensuring comfort and privacy for guests. A private home office just off the grand foyer adds functionality to this already impressive residence. Whether you’re seeking proximity to the course or the quiet luxury of an immaculate community in the heart of the North Fork, this property is truly a must-see.

350 Laurel Way, Laurel
$2,485,000
6 Beds ⋅ 4 Baths ⋅ 978923 MLS
Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

14 Freds Lane, Shelter Island
$1,900,000
3 Beds ⋅ 2 Baths ⋅ 980299 MLS
A rare and remarkable opportunity to own 22 sprawling acres on highly sought-after Sound Avenue in Riverhead. This unique property features a historic homestead dating back to the 1800s, offering timeless character and endless potential. Surrounded by the natural beauty of the North Fork, the expansive land which extends to Sound Shore Road, provides the perfect setting for agricultural use, or an opportunity to own your own farm/winery. The existing home showcases classic charm with original details, ready to be restored, expanded, or reimagined to suit your vision. With wide open fields and prime frontage along Sound Avenue, this property delivers both privacy and convenience—just moments from local farms, wineries, beaches, and all that Riverhead and the North Fork have to offer. Whether you’re looking to create a legacy property, invest in land, or embrace the North Fork lifestyle, this is a truly exceptional offering with limitless possibilities.

5528 Sound Avenue, Riverhead
$4,350,000
3 Beds ⋅ 2 Baths ⋅ 976938 MLS
MAGIC ON OREGON ROAD Romance, Elegance and Timeless beauty over 38 acres on bucolic Oregon Road, you couldn't ask for anything more! 36 acres of DRS land which includes 30 planted acres of grape vines, deer fencing and bird netting, irrigation in place for an additional 2-3 acres of planting and a potential wine tasting area. The updated vintage farmhouse rests on 2 acres of DRI land and features 3 bedrooms, 2 bathrooms, sun drenched open floor plan, eat-in-kitchen, dining area, sitting area with reading nook, living room with a fireplace. Step outside and enjoy lush landscape surrounding the pool, outdoor shower and vineyard views! Surrounded by award winning North Fork wineries, restaurants, farm stands, boating & great shopping.

2600 Oregon Road, Mattituck
$3,695,000
6 Beds ⋅ 6 Baths ⋅ 978627 MLS
Rising along one of the most prestigious stretches of shoreline in Asharoken, this extraordinary waterfront estate represents the largest and most significant residential offerings in the area. Set on approximately 3.43 private, gated acres with an impressive 400 feet of direct sandy beachfront along the Long Island Sound, the property offers exceptional scale, privacy, and uninterrupted water views near Northport Harbor. Encompassing approximately 12,000 square feet, this custom residence is designed for both grand scale entertaining and everyday living. Expansive, light filled interiors feature soaring ceilings, oversized rooms, and walls of glass that capture panoramic waterfront views from nearly every vantage point. Each bedroom is positioned to take full advantage of the coastal setting, offering a private retreat with sweeping water vistas. The home features 6 bedrooms and 6 bathrooms, along with two full kitchens, including a chef’s kitchen with direct outdoor access for seamless indoor outdoor flow. A butler’s kitchen further enhances convenience and entertaining capabilities. Resort style amenities include a saltwater indoor pool, private indoor racquetball court, and a marble spa-style bath. Additional highlights include separate guest quarters and a full length mahogany deck overlooking the harbor, ideal for enjoying sunrise and sunset views. The exterior grounds are equally impressive, featuring custom hardscape with a covered patio, fireplace, and expansive entertaining areas. The property’s 400 feet of private beachfront provides direct water access and a rare sense of seclusion. Modern upgrades include a whole-house generator and a private solar farm. Elevation certificate on file. A rare opportunity to own a premier waterfront estate on Long Island’s North Shore, offering a unique combination of size, setting, and lifestyle with convenient access to Manhattan.

33 Beach Road, Asharoken
$3,695,000
6 Beds ⋅ 6 Baths ⋅ 978356 MLS
Rising along one of the most prestigious stretches of shoreline in Asharoken, this extraordinary waterfront estate represents the largest and most significant residential offerings in the area. Set on approximately 3.43 private, gated acres with an impressive 400 feet of direct sandy beachfront along the Long Island Sound, the property offers exceptional scale, privacy, and uninterrupted water views near Northport Harbor. Encompassing approximately 12,000 square feet, this custom residence is designed for both grand scale entertaining and everyday living. Expansive, light filled interiors feature soaring ceilings, oversized rooms, and walls of glass that capture panoramic waterfront views from nearly every vantage point. Each bedroom is positioned to take full advantage of the coastal setting, offering a private retreat with sweeping water vistas. Per FEMA maps, the residence is located in Zone X with Elevation Certificate on file. Buyer to obtain independent flood determination. The home features 6 bedrooms and 6 bathrooms, along with two full kitchens, including a chef’s kitchen with direct outdoor access for seamless indoor outdoor flow. A butler’s kitchen further enhances convenience and entertaining capabilities. Resort style amenities include a saltwater indoor pool, private indoor racquetball court, and a marble spa-style bath. Additional highlights include separate guest quarters and a full length mahogany deck overlooking the harbor, ideal for enjoying sunrise and sunset views. The exterior grounds are equally impressive, featuring custom hardscape with a covered patio, fireplace, and expansive entertaining areas. The property’s 400 feet of private beachfront provides direct water access and a rare sense of seclusion. Modern upgrades include a whole-house generator and a private solar farm. A rare opportunity to own a premier waterfront estate on Long Island’s North Shore, offering a unique combination of size, setting, and lifestyle with convenient access to Manhattan.

33 Beach Road, Northport
$695,000
2 Beds ⋅ 3 Baths ⋅ 975429 MLS
Enjoy Coastal Living in the River View ... a Beautiful and Gated Waterfront Community! This renovated 2 bedroom, 2.5 bath Townhouse boasts a NEW modern kitchen with center island, refinished hardwood flooring, and sliding doors to the back deck offering water views. The spacious and open floor plan is bright and inviting, with tall ceilings and new LED Hi-Hat lighting throughout the entire home, while the lower level offers additional space for your enjoyment. The entry foyer is recently renovated with new flooring, radiant heat and access to the attached garage which offers a loft for additional storage. NOTE: Missing Railings on Staircases will be installed within the next couple of weeks, NEW from Deer Park Stairs.

123 Jackie Court, Patchogue
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 977905 MLS
Discover your ideal retreat in Shinnecock Shores! This two-story residence is perfect for dual-family living, boasting 4 bedrooms, an office, a bonus room, and 3 full bathrooms, all complemented by breathtaking bay views. The home features a 1 car garage and was raised to FEMA compliant height in 2014. The outdoor area is a paradise for water enthusiasts, featuring a private dock with a 75-foot vinyl bulkhead installed in 2021, a roomy shed, a cozy fire pit, and east-facing decks perfect for capturing stunning sunrises. Shinnecock Shores community provides exclusive access to bay beaches, a playground, and deep water canals that lead straight to Shinnecock Bay. Whether you're seeking a tranquil escape or a savvy investment, this property offers endless possibilities. This property is being sold as-is.

15 Marlin Road, E. Quogue
$6,895,000
7 Beds ⋅ 10 Baths ⋅ 977545 MLS
Brand New Modern Sag Harbor Construction by Thread Collective Expansive New Construction in Sag Harbor Introducing a now completed modern masterpiece by Thread Collective Architects. Featuring 8,500sf of luxury and comfort with 7 bedrooms and 10 baths on 0.68+/- acres. This beautiful home includes a saltwater pool, spa, and pool house. Just moments away from Sag Harbor Village amenities and convenient to Sagg Main Ocean Beach. Additional amenities include a sauna, steam bath, 6 indoor fireplaces, and one outdoor fireplace. The lower level is expansive with a bar/wine and plenty of room for a gym, game room or however you would like to customize. There are four laundry areas. All bathroom floors are radiant heat. Handmade white oak cabinetry. Real white oak floors. This is a fantastic lot backing to county-owned easement with views and access to Long Pond.

22 Round Pond Lane, Sag Harbor
$4,500,000
5 Beds ⋅ 3 Baths ⋅ 977357 MLS
Introducing a rare oceanfront masterpiece in the coveted enclave of Ocean Bay Park on Fire Island, ideally positioned along the border of Point O’ Woods. This custom-built home offers an exceptional level of privacy, complete with semi-private beach access via a dedicated walkway. Designed to capture the essence of coastal living, the home showcases unobstructed, panoramic views of the Atlantic Ocean and the Great South Bay from nearly every vantage point. A stunning roof deck crowns the property, delivering breathtaking 360-degree water views—perfect for sunrise coffees, sunset cocktails, and stargazing under the open sky. Whether you’re relaxing beside the pool or enjoying the serenity of your own stretch of beach, the natural beauty surrounding you is unparalleled. Watch dolphins glide by, whales breach in the distance, and waves roll endlessly to shore—all from the comfort of your private retreat. Seamlessly blending indoor and outdoor living, this one-of-a-kind residence offers tranquility, exclusivity, and an elevated Fire Island lifestyle in one of its most desirable communities.

37 Traffic Avenue, Ocean Bay Park
$1,445,000
3 Beds ⋅ 2 Baths ⋅ 975344 MLS
Boaters Dream! Located in Southold, this 3-bedroom, 2-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen includes modern appliances and ample counter space. Large windows provide natural light and water views, with direct access to the rear deck. The outdoor space includes a spacious deck with room for seating and dining, along with a gas grill setup. The dock provides convenient access for boating, kayaking, and other activities. The home includes three bedrooms and two bathrooms, offering flexible space for a variety of living arrangements. Additional features include well-maintained interiors and updated elements throughout. Conveniently located near local wineries, restaurants, and shops, with access to all that the North Fork has to offer.

470 Windy Point Lane, Southold
$17,900,000
975962 MLS
Positioned on prestigious Dune Road, just moments from the Atlantic Ocean and the Shinnecock Inlet, 369 Dune Road presents a singular opportunity to acquire one of the Hamptons' most recognized waterfront destinations. Home to the iconic Sundays on the Bay, this fully operational restaurant and marina combines hospitality, marine infrastructure, and irreplaceable location in one exceptional offering. Set against panoramic sunset views over the bay, the restaurant features 118 indoor seats framed by expansive windows that capture the waterfront setting, along with a spacious outdoor deck offering an additional 77 seats and two full-service bars. The atmosphere is vibrant yet refined - a proven draw for locals, seasonal residents, and boating clientele alike. The marina is equally compelling, offering 30 deepwater slips accommodating vessels up to 90 feet, with direct Atlantic access via the Shinnecock Inlet - ideal for sportfishing yachts and luxury craft. The property includes a fuel dock with approximately 12,000 gallons of diesel and 10,000 gallons of gasoline storage capacity, a well-maintained bulkhead, and professional-grade marine infrastructure. Additional improvements include a ±2,000-square-foot accessory structure currently utilized as an ice house, providing flexibility for expanded marine or hospitality use. With its unmatched waterfront exposure, established reputation, and rare zoning profile, 369 Dune Road offers extraordinary potential for continued hospitality operations, marina expansion, or strategic waterfront redevelopment. Opportunities of this scale and visibility on Dune Road are exceptionally rare. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

369 Dune Road, Hampton Bays

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