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1541 Stillwater Avenue, Cutchogue
$1,549,000
4 Beds ⋅ 3 Baths ⋅ 1044048 MLS
Welcome to The Vineyard House nestled between Peconic Bay Vineyard and East Creek—one of Cutchogue’s most coveted coastal enclaves—where 1541 Stillwater Avenue offers an exceptional opportunity to own in a high-value North Fork location. A short stroll leads to Pequash Beach, one of the finest stretches of bay shoreline on the North Fork. This transitional 4-bedroom, 3-full bath residence has been meticulously updated and is ideally positioned on a beautiful secluded property just shy of one acre, featuring stunning vineyard views, relaxing sunsets and room for a pool. The highly desirable layout features a skylit sunroom surrounded by nature, perfect for relaxation. The open floor plan features a spacious formal living room and library, with room for a piano, custom built in bookshelves and hardwood floors. A central dining room area leads to a separate den with a brick wood-burning fireplace and patio doors to a wrap around deck. Large, modern chef's kitchen with custom cabinetry, a separate pantry, wine bar, quartz countertops and luxury Wolf stove. A convenient ground-floor bedroom includes an updated full bathroom. Additionally, 3 bedrooms and 2 full bathrooms upstairs provide ample space for entertaining. Finished basement includes a media room, office space, and a separate laundry room. Attached 2 car garage and utilities room. The deck offers serenity surrounded by mature landscaping, privacy trees and a creek view that expands during the winter months. Set in a premier neighborhood known for its coastal lifestyle and award winning wines, this home is just moments from pristine beaches, vineyards, farm stands, and everything that makes the North Fork unique. Whether you’re seeking a year-round residence, weekend retreat, or investment in a sought-after beach and vineyard community, this property delivers. Swim, kayak, and keep a motor boat at the Shagwong Marina all within walking distance of your home. A brand new playground at Pequash Beach. Just 80 miles from New York City, and the Hampton Jitney stops right in Cutchogue. Mint condition home, photos and furniture in rooms are real - a great home to tour and make your next retreat.

1541 Stillwater Avenue, Cutchogue
1405 Bay Avenue, Mattituck
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 1042346 MLS
Welcome to a truly unique North Fork opportunity in the heart of Mattituck! This special property offers a charming 2-bedroom, 2-bath main residence along with a separate seasonal 2-bedroom, 1-bath cottage—perfect for guests, extended family, or additional seasonal possibilities. Enjoy access to a private dock, making it easy to embrace the best of waterfront living and spend your days out on the water. Ideally situated near Mattituck’s renowned vineyards, farm stands, beaches, restaurants, and all that the North Fork has to offer. Whether you’re searching for a year-round residence, weekend escape, or a property with incredible versatility, this one offers a rare combination of location, lifestyle, and opportunity. LB Not responsible for Info contained in the listing buyer must verify all info

1405 Bay Avenue, Mattituck
2625 Great Peconic Bay Boulevard, Laurel
$774,000
3 Beds ⋅ 2 Baths ⋅ 1042007 MLS
Set beside the natural beauty of Brush’s Creek Preserve in the peaceful North Fork hamlet of Laurel, this classic ranch offers comfortable single-level living, a private garden setting and an exceptional opportunity to make a home your own. The inviting floor plan features a living room, formal dining room, den, kitchen, three bedrooms, two full bathrooms and a dedicated laundry area, complemented by solid oak flooring throughout. A full basement and attached one-car garage provide valuable storage and additional possibilities. Outdoors, the approximately .30-acre property features established greenery and a private patio ideal for relaxing and entertaining, with potential room for a pool, subject to permits. Enjoy access to Mattituck Park District parks and beaches, including Veterans Beach on Peconic Bay and Breakwater Beach on Long Island Sound, along with nearby Bailie Beach, community recreation and the everyday pleasures of North Fork living. Vineyards, farm stands, boating, beaches and the shops, restaurants and charm of Love Lane are all within easy reach. Central air conditioning, along with a whole-house generator offers added comfort and continuity during unexpected power outages. The propane supply may also provide flexibility for future indoor or outdoor kitchen enhancements. Located within the Mattituck-Cutchogue School District and among the North Fork’s most accessible homeownership opportunities, this well-positioned property combines practical comforts, natural surroundings and an enviable lifestyle—ready for its next chapter.

2625 Great Peconic Bay Boulevard, Laurel
3651 Soundview Avenue, Peconic
$3,100,000
3 Beds ⋅ 2 Baths ⋅ 1009245 MLS
Charming updated Soundfront beach house! This home is what dreams are made of. Steps away is a plush, powder white sandy path leading to a serene private beach where panoramic vistas and mesmerizing sunsets will sweep you off your feet. Offering approximately 1,600 sq. ft. of living space, the first level boasts an eat-in-kitchen, living room with fireplace to cozy up to during those brisk fall evenings, access to a 110 sq. ft. screened-in porch - perfect for enjoying your morning coffee, a family room/dining area with soaring pitched ceilings, a full bath, laundry room and a bonus room that is currently used as a bedroom. Two additional bedrooms are located on the second floor - both with water views. There is also a new HVAC system in place. A multitude of opportunities await. This property is also offered as a compound. See 3645 Soundview Ave.

3651 Soundview Avenue, Peconic
3645 Soundview Avenue, Peconic
$3,300,000
4 Beds ⋅ 3 Baths ⋅ 1007876 MLS
North Fork retreat! A powder white sandy path leads to a gorgeous private beach offering 116 ft. of waterfrontage while incredible sparkling Sound views, sunsets, and lush greenery set this property apart. Enjoy water views from the open concept main level and the expansive 800+ sq. ft. rear deck - perfect for lounging, al fresco dining and taking in the fresh sea air. With over 3,000 sq. ft. of living space and an unfinished basement that offers an additional shy 1,000 sq. ft. without the 2-car attached garage, there is ample space for entertaining and to accommodate large gatherings. The first level includes a living/dining room and kitchen that flow seamlessly into one another while walls of glass allow natural light to saturate the space and provide access to the deck. There is also a bonus room conveniently located on the first floor. The second level boasts an oversized 800+ sq. ft. primary suite - also with gleaming water views, which can be divided into two ensuites. Two additional bedrooms and a full bath complete this level. All baths are updated and there are new HVAC and water filtrations systems in place. There is oil heat with the oil tank located in the basement. This property is also offered as a compound. See 3651 Soundview Ave.

3645 Soundview Avenue, Peconic
275 Pinewood Road, Cutchogue
$1,799,000
6 Beds ⋅ 4 Baths ⋅ 1038993 MLS
Welcome to The Waverly at Fleet’s Neck—one of Cutchogue’s most coveted coastal enclaves—where 275 Pinewood Road offers an exceptional opportunity to own in a high-value North Fork location with private beach rights to one of the finest stretches of shoreline on the North Fork. This captivating 6-bedroom, 4-bath residence, featuring new town water and a National Grid gas hookup, is ideally positioned on a beautiful property with a building permit already secured for a 16x32" heated saltwater pool. A highly desirable layout includes a private ground-floor primary bedroom suite complete with a full bathroom and a spacious den. An additional 5 bedrooms provide ample space for entertaining. The open floor plan features a spacious living room with a wood-burning fireplace, hardwood floors, and a formal dining room. Modern kitchen features new white shaker cabinets, quartz countertops and stainless steel appliances. A sun porch sitting room has sliding glass doors leading to the deck. A separate laundry room includes a new washer and dryer. An Attached garage and large basement offer room for expansion. Set in a premier neighborhood known for its coastal lifestyle, this home is just moments from pristine beaches, vineyards, farm stands, and everything that makes the North Fork special. Whether you’re seeking a year-round residence, weekend retreat, or investment in a sought-after beach community, this property delivers. A rare opportunity to secure your place in Fleet’s Neck—where lifestyle, location, and long-term value converge. Swim, kayak, and keep a motor boat at the Shagwong Marina all walking distance from your home. A brand new playground at Pequash Beach. Just 80 miles from New York City, and the Hampton Jitney stops right in Cutchogue. Mint condition home, photos and furniture in rooms are real - a great home to tour and make your own.

275 Pinewood Road, Cutchogue
2450 Main Road, Laurel
$1,799,000
1037638 MLS
Situated at the headwaters of Brushes Creek in Laurel, this beautiful property on 10.06 acres offers 1000' of waterfront paradise with 'forever' views. The development rights are intact on this land, which includes a four stall horse barn with electricity and water nearby, an enormous custom barn/equipment shed (or shop) for large equipment, and a beautiful, permitted, fully renovated two bedroom mobile home. This parcel has so many possibilities. Equestrian paradise. Maybe your agri-business is looking for a main road location. Or maybe you're looking for a true luxury property, you have generous space for a multi-dwelling compound on this parcel. Use the mobile home as your 'construction home' and you have a perfect guest house when your dream home is complete. Are you looking for a building opportunity? Yes please. Please respect the owners privacy this property is shown by appointment only. We'd love to meet you there!

2450 Main Road, Laurel
2200 Aldrich Lane, Laurel
$915,000
4 Beds ⋅ 2 Baths ⋅ 1037377 MLS
Discover the ease and enjoyment of North Fork living in this inviting four-bedroom, two-bath ranch, perfectly positioned on a full acre in Laurel. Designed for effortless one-floor living, the home offers a comfortable, practical layout highlighted by vaulted ceilings in the kitchen, living and dining rooms, creating an open and airy atmosphere. A wood-burning stove adds warmth, character and a cozy gathering place to the living room. Outdoors, the expansive property provides wonderful space for entertaining, gardening, recreation, or simply relaxing amid peaceful natural surroundings—with adjacent preserved land creating a beautiful and private backdrop. Whether you are seeking a welcoming year-round residence or an easy weekend escape, this property places you close to everything that makes the North Fork so special. Located within the popular Mattituck-Cutchogue School District, it is convenient to Love Lane, shopping, restaurants, farm stands and celebrated local wineries, while nearly equidistant from Breakwater and Bailie’s beaches on Long Island Sound and Veterans Memorial Park Beach on Peconic Bay. Space, privacy, convenience and possibility—all in one appealing Laurel location. Some images presented feature ai generated staging.

2200 Aldrich Lane, Laurel
1140 Park Avenue, Mattituck
$11,500,000
5 Beds ⋅ 5 Baths ⋅ 1036287 MLS
Welcome to one of the East End's most distinguished estates. This waterfront property, built in the early 1900s, is situated on 3.24 acres and offers 170 feet on one of the North Fork’s most coveted stretches of pristine coastline, overlooking Peconic Bay, This offering represents a legacy opportunity. Upon arrival, the grandeur of the home makes a lasting impression with its sprawling lawn, magnificent trees, manicured grounds, and classic New England-style residence featuring an understated wrap-around porch and porte-cochere entry. Several years ago, the residence underwent a meticulous renovation that preserved its historic features while incorporating modern design elements and craftsmanship, enhancing the home's timeless beauty amid its coastal setting. Entering through a grand vestibule, you are welcomed by a double set of wide wooden doors with large inset glass. The spacious formal living room, complete with exposed beams, detailed oak paneling, a wood-burning fireplace, and weight-and-chain windows, provides a warm atmosphere while embracing views of the bay. The open and airy dining room features sliding doors that lead to a covered porch and provides access to a quaint library for more intimate conversations. The home's kitchen is designed for entertaining and enjoys abundant natural light. It boasts an oversized island, chef-grade appliances, custom cabinetry, beautiful countertops, and a hostess pantry, combining functionality with elegance. The casual dining area in the sunroom is surrounded by windows, allowing natural light and showcasing cascading hydrangeas, perfect for enjoying sunrises. Additionally, there is a side door leading to a blue stone patio for outdoor cooking and access to the home's waterside yard. The sunroom also includes a small alcove with floor-to-ceiling windows, providing extra seating or a quaint office space that highlights the natural beauty outdoors. The open floor plan incorporates a lounge anchored by a gas fireplace, making hosting easy with the kitchen's close proximity. The intricate staircase, both restored and timeless, leads to the home's five bedrooms, three of which face south to maximize the views. The primary ensuite captures the waterfront view and includes a spa-inspired bathroom with a soaking tub and an oversized walk-in closet. The Jr. Primary ensuite is spacious and overlooks the backyard. Two additional bedrooms, also facing the water, share a full bathroom, while the final bedroom is ensuite and overlooks the side of the property. The residence features a unique, restored two-story boathouse, providing access to the double-tiered bulkhead and beach. This space is ideal for intimate gatherings and enjoying the sound of the waves. The expansive property additionally includes a Gunite pool with a covered outdoor lounge, a powder room, and a three-car garage. Encapsulated by mature trees and hedges, the property offers exceptional privacy and serenity. Whether you are looking for a summer sanctuary or a year-round estate, this property offers a level of prestige that rarely hits the market.

1140 Park Avenue, Mattituck
Mattituck
$4,500,000
2 Beds ⋅ 2 Baths ⋅ 1036267 MLS
A rare opportunity to own a piece of history on Laurel Lake, a 33 acre kettle lake located in the hamlet of Laurel just 1 1/2 miles southwest of Mattituck. The structure was originally built as a "hunting lodge" by the Beverwyck Brewing Company of Albany, NY and placed on the lake at the 1939-1940 World's Fair in Queens to promote its beer. After the fair, the structure was relocated to its new home on Laurel Lake with 126' of lake frontage. The property was extensively restored in 2019. You have to see it to believe it! No description will ever do it justice, but certainly nothing like this exists on the North Fork of Long Island. Whether you are an avid fisherman or just inclined to sit back and enjoy the wildlife the lake attracts, a world of peace, tranquility, and beauty awaits you.

Mattituck
365 Rachels Road, Mattituck
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 1033686 MLS
A Rare North Fork Farmhouse with a Heated Barn and Endless Possibilities Tucked away on three-quarters of an acre in a quiet Mattituck neighborhood, this beautifully updated North Fork farmhouse offers the perfect blend of timeless charm, modern updates, and exceptional versatility. Surrounded by a peaceful setting, the property provides plenty of room to relax, entertain, and enjoy the North Fork lifestyle, with thoughtfully designed indoor and outdoor spaces that make you feel right at home. Designed for comfortable living and effortless entertaining, the home features four bedrooms and four full bathrooms across three finished levels. The thoughtfully renovated interior showcases hardwood floors, custom millwork, a beautifully appointed quartz kitchen with shaker cabinetry, and a wood-burning fireplace that anchors the inviting living and dining areas. All four bathrooms feature radiant heated floors, providing comfort and warmth throughout the year. A first-floor bedroom and full bath provide flexibility for guests or single-level living, while the finished lower level—with an additional bedroom, full bath, and spacious family room—offers exceptional space for recreation, a home office, or extended stays. Upstairs, the primary suite features a generous walk-in closet and beautifully appointed bath, while the second upstairs bedroom also enjoys its own walk-in closet. A standing-seam metal roof, approximately five years old, adds lasting value and peace of mind. Step outside to enjoy a freshly painted rear deck overlooking a newly fenced backyard designed for outdoor living, complete with mature landscaping, a tranquil koi pond, hot tub, dedicated fenced garden area, charming playhouse, and abundant space for a future swimming pool. A truly exceptional feature is the property's heated nearly 1,000-square-foot galvanized steel barn with convenient secondary access from Main Road. Equipped with electricity, oversized doors, soaring ceilings, a durable 12-inch concrete floor, and a wood-burning stove, this remarkable space offers endless possibilities as an artist's studio, workshop, garage, collector's showcase, or substantial storage for boats, vehicles, equipment, and hobbies. Few North Fork properties combine an updated farmhouse with a heated barn of this size and versatility. Paired with its peaceful setting just minutes from Love Lane, the grocery store, beaches, wineries, and farm stands, this is a property that offers exceptional flexibility for the way people live today.

365 Rachels Road, Mattituck
1850 Highland Road, Cutchogue
$1,375,000
4 Beds ⋅ 3 Baths ⋅ 1018415 MLS
Welcome home to this four-bedroom two and and half bath expanded ranch style-home in the coveted Highland Estates section of Cutchogue. This corner property is set on 0.92 acres of flat landscaped property, which offers effortless indoor and outdoor living. The open concept kitchen has both Silestone and Butcher block countertops with modern floating shelves, ample cabinetry, white tiled backsplash and adequate prep space. The first floor primary suite provides a private retreat with easy access to the primary bath with tub. An inviting indoor-outdoor atrium sun-room generates the perfect space for relaxation and entertaining. There is a large family room, complete vaulted ceilings and a wood burning fireplace. Two additional upper level bedrooms and a full bathroom with walk in shower with glass surround, complete the upper level. Step outside to your own backyard oasis featuring a salt-water in-ground pool, outdoor cabana and lush landscaping, Multiple seating areas include a fire-pit, and separate grilling area. Out-door exterior lighting provide a tranquil atmosphere which allows for entertaining late into the evening, all designed to generate a peaceful setting right in the comfort of your home. A rare opportunity to own your own slice of paradise, in the sunniest place on Long Island, close to beaches, restaurants farm stands and wineries. Priced to sell, The house is being sold "as is". .

1850 Highland Road, Cutchogue
1540 Laurelwood Drive, Laurel
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 1030811 MLS
Set within Laurelwood Estates, a highly sought-after neighborhood, this spacious 4-bedroom, 3-bath Colonial on nearly one acre, features a comfortable, well designed layout with an attached 2 car garage, full walk-out basement, in-ground sprinklers and deeded access to the neighborhood’s private community beach. Enjoy the best of North Fork living, minutes from beautiful beaches, wineries, farm stands, shops, and restaurants.

1540 Laurelwood Drive, Laurel
1492 Skunk Lane, Cutchogue
$2,499,000
4 Beds ⋅ 5 Baths ⋅ 1028997 MLS
Vineyard Estate Living in the Heart of Cutchogue. Set on 2.44 private acres adjacent to a North Fork vineyard and a bucolic field, 1492 Skunk Lane offers the scale and flexibility of a country estate with the comfort and ease of modern living. A gracious New England-style covered porch and classic architecture create memorable curb appeal, while the interior unfolds with a welcoming flow designed for entertaining, working from home, and relaxed everyday living. With a new GAF roof installed Summer 2026, you're sure to spend comfortable days ahead with peace of mind. The entry foyer opens to a formal living room or dining room, and handsome library or home office with a gas fireplace. At the center of the home, the expansive eat-in kitchen provides generous counter space, abundant cabinetry and pantry storage, and an easy connection to the spacious great room. A second, wood burning, fireplace and access to the screened porch create an inviting setting for quiet evenings or gatherings overlooking the broad, verdant lawn. The main level also includes an en-suite guest bedroom, butler’s pantry, laundry and mudroom, and direct access to the oversized three-car garage. A private staircase leads to more than 700 square feet of finished bonus space with a powder room—ideal for a studio, private office, recreation room, or your personal crafts area. Upstairs, the serene primary suite features a private bath, extensive built-ins, ample closet space, and room to create a comfortable retreat. Two additional bedrooms share a Jack-and-Jill bath, while the third-floor mezzanine provides another quiet place to work, study, read, or create, together with access to substantial walk-up attic storage. The finished lower level further expands the home’s versatility with media and fitness areas, a bathroom, utility rooms, abundant storage, and convenient garage access. Outdoors, expansive and irrigated lawns, exceptional privacy, western exposure, and the adjoining vineyard create a peaceful backdrop for sunset entertaining. With ample room for a pool and additional outdoor living spaces, the property and the outdoor shower is equally suited to year-round resort-style living or a refined weekend retreat. Located minutes from Nassau Point’s Causeway Beach, Love Lane, farm stands, wineries, local shopping, and Greenport dining, 1492 Skunk Lane presents a distinctive opportunity to enjoy the beauty, space, and effortless lifestyle of the North Fork.

1492 Skunk Lane, Cutchogue
18 Beach, Laurel
$899,000
3 Beds ⋅ 3 Baths ⋅ 1026560 MLS
Experience spectacular sunrise-to-sunset views of the Great Peconic Bay from this charming North Fork beach house, ideally situated on a quiet, pristine lane in the desirable hamlet of Laurel. Just moments from a private sandy beach, this inviting retreat offers the ultimate coastal lifestyle. The home features 3 bedrooms and 1 bath, along with a bright enclosed porch showcasing stunning water views. A spacious deck provides the perfect setting for outdoor dining, entertaining, or simply relaxing while enjoying the bay breeze and breathtaking scenery. Adding exceptional value is a large detached 2-car garage with abundant storage and a legal second-story deck, offering endless possibilities for recreation, hobbies, or additional outdoor living space. An outdoor shower completes the quintessential beach house experience. A rare opportunity to own a true waterfront community retreat where every day feels like a vacation on the North Fork.

18 Beach, Laurel
2340 Fairway Drive, Cutchogue
$1,499,999
5 Beds ⋅ 4 Baths ⋅ 1024427 MLS
Perfectly positioned in the sought-after Fairway Farms community, this spacious 3,200-square-foot residence enjoys peaceful views overlooking the golf course while offering the best of North Fork living. Set on a beautifully landscaped 0.93-acre property, this home is just minutes from the charming hamlet of New Suffolk, Pequash Beach, vineyards, marinas, farm stands, and acclaimed restaurants. Designed for both comfortable everyday living and effortless entertaining, the home features five bedrooms, four full bathrooms, hardwood floors throughout, two fireplaces, an inviting eat-in kitchen, and a formal dining room. Bathed in natural light, the expansive enclosed porch offers a bright and inviting space to relax, dine, or entertain while taking in the tranquil views of the surrounding grounds and picturesque golf course. With walls of windows and an airy, open feel, it serves as a seamless extension of the home's living space and is sure to become a favorite gathering space. Step outside to your private backyard retreat featuring a fenced, heated gunite saltwater pool surrounded by elegant bluestone patio—an ideal setting for summer entertaining or quiet afternoons overlooking the manicured fairways. Additional highlights include natural gas heat, four-zone heating, a Navien on-demand hot water system, public water, underground utilities, newer appliances, in-ground irrigation, and a walk-in attic with outstanding potential. Whether you're searching for a year-round residence or the perfect North Fork getaway, this exceptional Fairway Farms property combines generous living space, a premier golf course setting, and an unbeatable location close to beaches, boating, wineries, and everything that makes Cutchogue one of Long Island's most desirable destinations. This listing may include images that have been digitally altered or virtually staged.

2340 Fairway Drive, Cutchogue
26170 County Road 48, Cutchogue
$649,000
4 Beds ⋅ 1 Baths ⋅ 1024859 MLS
This 4-bedroom, three-level home sits in the heart of Cutchogue — one of the North Fork's most coveted addresses. Offered strictly AS IS, WHERE IS, with no representations or warranties, this is a drive-by opportunity for the visionary, the investor, or the end-user ready to make their mark on a property with real bones. The appeal is clear: a two-car detached garage, solid frame construction, and the kind of understated presence that fits naturally into the North Fork landscape. Inside, based on the footprint and layout you have hardwood floors, an eat-in kitchen, forced-air oil heat, two levels of living space, a basement with Bilco doors, and a partial attic speak to a home with genuine structure and flexibility. And the surroundings? Unmatched. McCall Wine, Pellegrini, Pugliese, Suhru and Lieb Vineyards are practically at the doorstep. Farm stands overflow every season, and the Southold Historical Museum's Maple Lane Campus anchors the neighborhood in history and community. Opportunities like this on the North Fork don't wait. Sold with tenants.

26170 County Road 48, Cutchogue
6205 Alvahs Lane, Cutchogue
$699,000
3 Beds ⋅ 2 Baths ⋅ 956730 MLS
Nestled on a landscaped corner property in the heart of Cutchogue, this inviting three-bedroom, two-bath home offers comfort, privacy, and endless potential. A charming covered porch welcomes you into bright, open living spaces, while the spacious yard provides plenty of room to relax, entertain, or garden. Ideally located just minutes from Cutchogue Village, renowned wineries, farm stands, beaches, and marinas, this is a wonderful opportunity to enjoy the very best of North Fork living- whether as a year-round residence or weekend retreat.

6205 Alvahs Lane, Cutchogue
1775 Point Pleasant Road, Mattituck
$6,450,000
6 Beds ⋅ 8 Baths ⋅ 1021701 MLS
Introducing 1775 Point Pleasant, a newly constructed waterfront estate set on 1.8 acres with over 280 feet of pristine creek-frontage along iconic Mattituck Inlet. Thoughtfully designed and expertly crafted, this exceptional shingle sided Post-Modern style residence seamlessly blends timeless architecture with modern luxury. Spanning more than 7,000 square feet, the home showcases wide-plank hardwood flooring throughout, dual primary suites on both the first and second levels, a fully finished lower-level with private fitness studio, sauna, climate controlled wine storage, an unmatched custom lighting package, pre-wired recessed speaker system and expansive living spaces on all three levels designed for both everyday comfort and effortless entertaining. At the heart of the home is a chef's kitchen appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, multiple beverage stations and refined finishes throughout. Outdoors, resort-inspired amenities await, including a heated 22'x44' gunite pool surrounded by an expansive travertine terrace, fully equipped outdoor kitchen, a covered lounge with ceiling mounted heaters for those cooler nights and anchored by a third wood-burning fireplace, creating an ideal setting for waterfront entertaining. Finally, enjoy a manicured path of travertine stepping pads that lead to an oversized floating dock, equipped with water and electric, that can easily house a large boat with deep draft, perfectly capping off this incredible custom build opportunity. Offering an extraordinary combination of scale, privacy, craftsmanship, and lifestyle, 1775 Point Pleasant represents a rare opportunity to own a truly exceptional waterfront retreat on the North Fork.

1775 Point Pleasant Road, Mattituck
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
12950 Oregon Road, Cutchogue
$2,795,000
4 Beds ⋅ 4 Baths ⋅ 995201 MLS
Bucolic Cutchogue Compound. Set on iconic Oregon Road in Cutchogue, amongst farmstands and vineyards, this incredible 2 acre compound offers exactly the North Fork vibe everyone is looking for. The main house features 4 bedrooms and 3.5 bathrooms, opening out to a 20x44 in ground saltwater pool that quietly becomes the center of summer. Great flexible space throughout, generator ready, full basement, a 3 car garage and a separate studio with its own 4 car garage, giving you all the flexible space you need for guests, work, cars, or a full on creative or wellness setup. Minutes to beaches, restaurants, nature preserves, shopping, boating, and North Fork Country Club. Could be you!

12950 Oregon Road, Cutchogue
1350 W Cove Road, Cutchogue
$16,800,000
10 Beds ⋅ 11 Baths ⋅ 1015559 MLS
Nassau Point Waterfront Estate. Along the shores of the Peconic Bay, where boats drift past the coveted coastline of Nassau Point, an exceptional sunset side waterfront estate quietly commands attention. Spanning 4.25 acres with more than 300 feet of private beach, this remarkable property offers a rare blend of privacy, presence, and North Fork coastal beauty. The nearly 10,000-square-foot main residence sits gracefully within the landscape, designed to celebrate both the surrounding water and the art of refined living. Sunlight pours through expansive windows, illuminating generous entertaining spaces and framing panoramic bay views that shift beautifully throughout the day into the evening. The home features eight bedrooms and eight and a half bathrooms, thoughtfully arranged to create both comfort and space. A private screening room, gym, and sauna offers relaxation and recreation. A separate guest cottage with two bedrooms and two bathrooms provides a welcoming retreat for your guests, creating the perfect balance of independence and hospitality. Outside encompasses every aspect of waterfront resort living, boating from your deep water dock, swimming in the gunite pool to playing tennis or catching shade in the pool house and dining seaside while watching the sunset. Combining extraordinary scale, exceptional waterfront frontage, and a setting that captures the spirit of the North Fork, this Nassau Point compound offers a rare opportunity to own a truly distinguished coastal retreat - ideal as a legacy property or an unforgettable seasonal escape.

1350 W Cove Road, Cutchogue
4210 Ole Jule Lane, Mattituck
$1,850,000
2 Beds ⋅ 3 Baths ⋅ 1014736 MLS
Nestled along the tranquil shores of James Creek with effortless access to the Great Peconic Bay, this inviting waterfront residence offers the perfect blend of comfort, recreation, and coastal charm. A newly installed deep-water floating dock and access to a private association bay beach make it an exceptional opportunity for boating enthusiasts and those seeking a connection to the water. Inside, the home is bright and welcoming, featuring an open-concept layout with hardwood flooring throughout and soaring vaulted ceilings that fill the eat-in kitchen with natural light. Privately situated on its own wing of the main level, the primary suite offers a spacious walk-in closet and en-suite bath, creating a comfortable retreat within the home. The second floor provides exceptional flexibility with an expansive landing area ideal for a media room, home office, or additional lounge space. A generously sized guest bedroom, full hallway bath, abundant storage, and a substantial bonus room above the attached two-car garage complete the upper level. Set on nearly one-half acre with approximately 100 feet of waterfront frontage, the property is thoughtfully positioned to take advantage of its waterfront setting. The current floating dock accommodates a 36-foot vessel with twin outboard engines, offering ample water depth for a variety of boating needs. Completing the offering is access to a nearby community bay beach, providing yet another way to enjoy this sought-after North Fork waterfront location.

4210 Ole Jule Lane, Mattituck
865 Track Avenue, Cutchogue
$895,000
2 Beds ⋅ 1 Baths ⋅ 986841 MLS
Some things are worth holding onto and this one is no exception. Nestled in one of the North Fork's most coveted beachside enclaves, this authentic mid-century modern gem offers the rare combination of style, privacy and beach access to one of the best bay beaches in the region! The detached 2-car garage handles the practical side of life beautifully with owned solar panels, including backup battery, while the working vegetable garden reminds you that the good life really is grown here. There's room for a pool, room to expand, and plenty of room to exhale. Optional membership in the Fleets Neck Property Owners Association gets you access to a private bay beach on the east end of Dave Allison Beach - plus storage for two kayaks. This is the kind of property that smart buyers recognize immediately - and move on quickly. The bones are right. The location is right. The potential? Even better.

865 Track Avenue, Cutchogue
5475 Bergen Avenue, Mattituck
$699,000
1010671 MLS
North Fork Opportunity — Calling All Visionaries, Architects & Dream Builders! Ride the North Fork wave and bring your vision to life! A unique opportunity to own land in Mattituck and create something truly your own — whether it’s a year-round residence, weekend retreat, or a thoughtfully designed custom home. Calling all architects, builders, and visionaries — bring your plans, creativity, and imagination. This is your blank canvas to design a space that reflects your lifestyle and take advantage of the opportunity to build from the ground up. Enjoy everything the North Fork experience has to offer, from nearby beaches and boating to vineyards, farm stands, restaurants, and charming local destinations. With continued interest in the North Fork, opportunities to create something new continue to capture attention. Your vision. Your design. Your North Fork chapter starts here.

5475 Bergen Avenue, Mattituck
420 Sigsbee Road, Mattituck
$759,000
2 Beds ⋅ 1 Baths ⋅ 1011722 MLS
Nestled in the desirable Sigsbee community of Mattituck, this delightful two-bedroom, one-bathroom cottage offers the perfect blend of privacy, convenience, and coastal living. Set on a spacious lot with a large backyard, the property provides a peaceful setting for relaxing, entertaining, or enjoying summer evenings outdoors. Inside, the home features a bright and inviting layout with comfortable living spaces and timeless cottage charm. Whether you’re looking for a year-round residence, weekend getaway, or investment opportunity, this home offers endless potential. Enjoy exclusive access to the community’s private association beach nearby, perfect for swimming, kayaking, paddleboarding, or simply taking in the stunning expansive white sandy beach. Conveniently located near Mattituck’s shops, restaurants, wineries, farm stands, and transportation, this property allows you to experience the best of North Fork living while maintaining a tranquil retreat-like atmosphere. A rare opportunity to own a charming beach-community home with a generous backyard and private beach rights in one of Mattituck’s most sought-after neighborhoods. This listing may include images that have been digitally altered or virtually staged.

420 Sigsbee Road, Mattituck
8155 Route 25, Mattituck
$625,000
1006809 MLS
Excellent opportunity! Attention investors! vacant commercial shy acre lot in high traffic location Dec approval

8155 Route 25, Mattituck
6200 New Suffolk Avenue, Mattituck
$715,000
3 Beds ⋅ 2 Baths ⋅ 995496 MLS
6200 New Suffolk Ave, Mattituck, NY 3 Bedrooms | 1.5 Baths | Full Basement | Over 1/2 Acre Move-in ready needs a little love or your custom upgrade, his three-bedroom, one-and-a-half-bath home situated on over half an acre in the heart of Mattituck’s sought-after North Fork community. This property offers a functional layout, full basement with storage and expansion potential, oil heat, and spacious outdoor property with room to enjoy year-round or seasonally. Ideally located just minutes from local beaches including Veterans Memorial Park and Breakwater Beach, as well as nearby wineries, farm stands, marinas, and nature preserves. Conveniently close to Love Lane featuring boutique shopping, cafés, and local dining. Nearby North Fork attractions include Macari Vineyards, Bedell Cellars, and additional wineries, restaurants, hiking trails, and waterfront recreation throughout the area. Approximate beach permit fees and access may vary and should be independently verified by buyers. Property information, permits, taxes, square footage, and all details should be independently confirmed by purchaser and purchaser’s representatives. A rare opportunity to own in one of the North Fork’s most desirable coastal communities with convenient access to beaches, vineyards, dining, and outdoor recreation.

6200 New Suffolk Avenue, Mattituck
3123 & 3595 Skunk Lane, Cutchogue
$7,775,000
1003778 MLS
Rarely does an opportunity of this magnitude surface on the North Fork - 44 contiguous acres of pristine, development-rights-intact land in the heart of Cutchogue, steps from the coveted Nassau Point Causeway Beach on Little Peconic Bay. This assemblage encompasses buildable terrain with sweeping sky and farmland vistas, coming to market at a pivotal moment in the North Fork's transformation into one of the East End's most sought-after locales. Full flexibility for a conservation subdivision, private estate, or boutique residential enclave, this is an end user, builder, or visionary's moment. The North Fork land market is moving - and properties of this scale, integrity, and proximity to the water do not wait.

3123 & 3595 Skunk Lane, Cutchogue
315 Wicks Road, New Suffolk
$825,000
3 Beds ⋅ 2 Baths ⋅ 1003057 MLS
Tucked away in the coveted waterfront hamlet of New Suffolk, this charming move-in ready ranch captures the easygoing spirit of North Fork living. Warm hardwood floors run throughout the home, where an inviting living and dining area flows effortlessly into a bright, sun-filled kitchen overlooking the backyard gardens. The layout offers two comfortable guest bedrooms, a full hall bath, and a private primary suite with its own full bath, walk-in closet, and laundry area. Outside, the property feels peaceful and established, with lush green lawns, thoughtfully maintained garden beds, and a vegetable garden tucked along the rear of the yard. Just moments from the beloved New Suffolk beach, local favorites like Minnow and Legends Restaurant, and Shagwong Marina, the location places you right in the heart of one of the North Fork’s most cherished waterfront communities. Whether envisioned as a quiet weekend escape or a year-round home, life in New Suffolk offers a timeless coastal charm that never goes out of style.

315 Wicks Road, New Suffolk

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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