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$1,195,000
4 Beds ⋅ 2 Baths ⋅ 1033174 MLS
A rare opportunity to own a remarkable piece of history, this beautifully preserved residence seamlessly blends Colonial origins with timeless Georgian elegance. Originally built circa 1770, the home has evolved through generations of thoughtful additions and renovations while retaining its extraordinary architectural character. The gracious center hall floor plan welcomes you with a historic staircase and spacious rooms filled with period charm. A stunning 14 x 25 country kitchen, added around 1820, features soaring cathedral ceilings, a loft overlooking the space, ample room for everyday dining, and direct access to a private terrace—perfect for entertaining or enjoying peaceful mornings outdoors. Historic details abound throughout the home, including exposed hand-hewn oak beams in the formal dining room, exceptionally wide-plank wood floors measuring up to 18 inches on the second level, elegant period moldings, and beautiful marble fireplaces. A major Georgian-style renovation completed between 1850 and 1860 introduced the stately entrance portico, the full two-story roofline, and the impressive 40-inch-wide staircase, enhancing both the home’s beauty and functionality. Offering four bedrooms and two full bathrooms—one on each level—the home combines historic craftsmanship with comfortable everyday living. Complementing the residence is a carriage barn-style garage, built in 2003, featuring space for three vehicles, a spacious second-floor loft ideal for a studio, workshop, storage, or future possibilities, plus an attached tool shed. Situated on a generously sized parcel with .93 acres, the property is framed by mature trees that provide privacy while the expansive lawn offers endless opportunities for gardening, recreation, entertaining, or future enhancements. Rich in history, craftsmanship, and character, this one-of-a-kind property offers the rare chance to own a home where over 250 years of architectural heritage meet the comforts of modern living.

115 Highland Road, Cutchogue
$1,425,000
4 Beds ⋅ 4 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. Set of .92 acres offering effortless indoor-outdoor living. The open concept kitchen offers both Silestone and Butcher block countertops with modern floating shelves and ample cabinetry. 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 creates the perfect spacer for relaxation and entertaining. The family room has a wood burning fireplace to cozy up to on those cold winter days. Two additional upper level bedrooms and full bath 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. The out-door lighting provides a tranquil atmosphere allowing for to entertaining into the evening,, all designed to provide a peaceful setting right in the comfort of your home. A rare opportunity to own your own slice of paradise, close to beaches, restaurants and wineries. Priced to sell House is being sold as is. .

1850 Highland Road, Cutchogue
$749,999
2 Beds ⋅ 1 Baths ⋅ 1032813 MLS
Welcome to this beautifully renovated ranch nestled in the heart of Cutchogue! This charming home offers two spacious bedrooms, one full bathroom, and a bright, inviting layout that’s perfect for comfortable everyday living. Enjoy year-round comfort with central air conditioning and forced-air heating. The full unfinished basement provides endless possibilities for additional living space, storage, or a custom renovation to fit your needs. Located in a beautiful and highly desirable area, this home combines modern updates with timeless charm. Don’t miss this incredible opportunity to own a move-in-ready home in one of the North Fork’s most sought-after communities!

24485 Main Road, Mattituck
$2,745,000
4 Beds ⋅ 4 Baths ⋅ 1029802 MLS
Situated on over two acres within an exclusive cul-de-sac, this newly constructed residence built by renowned builder Southampton Building Company Corp., is now on the market! The home is just moments from Breakwater Beach, the Long Island Sound and Mattituck Inlet, offering convenient access to beaches, boating and the best of North Fork living. The Developer features four bedrooms and four full bathrooms, including two luxurious primary suites, one conveniently located on the first floor and another on the second. The chef’s kitchen is appointed with top-tier appliances, including a 48-inch dual-fuel double-oven range, professional-grade vent hood and wine refrigerator, creating a space that is as functional as it is beautiful. A sprawling lower level with 10-foot ceilings, three egress windows and a private exterior entrance offers exceptional flexibility for recreation, wellness, or future customization. A fully customizable and expandable smart-home system, radiant-heated flooring throughout, custom-designed closets and premium finishes throughout reflect an exceptional level of quality and craftsmanship. Builders 5000 sq.ft. expansive patios extend the living spaces outdoors, creating an inviting setting for entertaining and relaxation. The private backyard is highlighted by a spectacular 20-by-60-ft heated saltwater pool with an automatic cover, along with a dedicated sport court designed for pickleball and basketball. Combining exceptional design, uncompromising quality, and an irreplaceable location, this is a rare opportunity to own a true legacy property in one of Mattituck’s most desirable enclaves. Home includes three levels of furnishings, full arborvitae privacy screening and an extensive new construction warranty package for the home and pool

2790 Stanley Road, Mattituck
$950,000
4 Beds ⋅ 3 Baths ⋅ 1030931 MLS
Highlights: • Vintage 1963 home on 1.25 private acres • 4 bedrooms | 2.5 baths • Spacious, functional floor plan with endless potential • Formal living room plus separate den • Eat-in kitchen • Office/flex space on both the first and second floors • Abundant storage throughout • Full basement • Plenty of room for a pool (subject to permits) • Close to local beache Built in 1963, this vintage home presents a rare opportunity to bring your vision to life. Set on a beautiful 1.25-acre parcel, the home features a generous and thoughtfully designed layout with four bedrooms, two-and-a-half baths, formal living and dining spaces, a separate den, an eat-in kitchen, and flexible office areas on both the first and second floors. Original details add character, while the spacious floor plan provides an exceptional foundation for renovation, restoration, or a complete reimagining. With ample room for a pool and possibilities both inside and out, this is a property where vision, design, and location come together to create something special.

865 Peconic Bay Boulevard, Laurel
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 1027823 MLS
Welcome home to this North Fork retreat! The perfect getaway for peace and relaxation. Tucked away on a charming lane, this beautifully maintained home and features a resort-style yard centered around an in-ground pool and patio, creating the ultimate setting for entertaining. Inside this renovated home, there is plenty of room for everyone and offers a seamless flow between indoor and outdoor living. Location is everything, and this property has it all. Take a short stroll to the beach for swimming, kayaking, paddle boarding. Boating and fishing enthusiasts will appreciate being just down the road from Strong’s Marina, offering easy access to the best boating on The Peconic Bay. Whether you’re searching for a full-time residence, weekend escape, or investment opportunity, this home has it all. Close to Love Lane, shopping, restaurants, wineries, transportation and all the best Mattituck has to offer.

475 Alois Lane, Mattituck
$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
$749,999
4 Beds ⋅ 2 Baths ⋅ 1030041 MLS
Welcome to 1765 Delmar Drive, a charming ranch tucked away in the heart of beautiful Laurel, NY. Enjoy the best of North Fork living with deeded bay beach and park rights, including 200 feet of pristine waterfront, just a short stroll from your front door. Set on over a half-acre, this inviting home offers easy one-level living with a thoughtfully designed floor plan ideal for everyday comfort and effortless entertaining. Featuring 4 spacious bedrooms and 2 full bathrooms, including a private primary ensuite, the home also boasts a bright, oversized eat-in kitchen with soaring vaulted ceilings and an inviting living room centered around a cozy wood-burning fireplace. The attached two-car garage provides convenient access to a full basement with impressive 9-foot ceilings, offering abundant storage and endless possibilities for future living space, a home gym, recreation area or whatever your vision may be. Step outside to your own private backyard retreat featuring a large screened-in porch, in-ground sprinkler system, and a fully fenced yard overlooking peaceful farmland views—creating the perfect setting for morning coffee, summer gatherings, or simply enjoying the tranquility of the North Fork. Ideally located near acclaimed wineries, breweries, farm stands, golf courses, gourmet restaurants, boutique shopping on Love Lane, and countless agricultural attractions, this home also offers easy access to the Hampton Jitney or LIRR for convenient trips to and from New York City. Whether you're searching for a year-round residence or the perfect North Fork getaway, 1765 Delmar Drive offers an exceptional opportunity to enjoy the relaxed coastal lifestyle you've been dreaming of. Don't miss this opportunity!

1765 Delmar Drive, Laurel
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 1027794 MLS
This impeccably maintained residence is perfectly positioned in the heart of Mattituck, just minutes from local beaches, Love Lane, New Suffolk, and downtown Cutchogue. Set on a beautifully landscaped acre, the property offers a large in-ground pool, mature gardens, and ample room to add additional amenities such as a tennis court or accessory structure. Inside, a bright, open-concept floor plan lends itself to both everyday living and entertaining, featuring a large chefs kitchen, dining room and living room. The oversized primary suite serves as a private retreat, complete with a spacious en-suite bath and generous walk-in closets. Two additional guest bedrooms and a large home office provide flexibility for visitors, or remote work. A large laundry room, basement and detached garage provide for additional utility. Sit on your back patio overlooking the pool to take in spectacular East End sunsets. Thoughtfully maintained and ideally located, this is a home that pairs comfort, convenience, and future potential in one of the North Fork's most desirable communities.

1430 Marratooka Road, Mattituck
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 1025976 MLS
Newly renovated and masterfully designed, this exceptional home features three spacious ensuite bedrooms, plus an additional bedroom on the walk-out lower level. The open-concept floor plan with soaring ceilings, is highlighted by dramatic floor-to-ceiling windows and doors that frame breathtaking panoramic views of the surrounding landscape while filling the home with natural light. This is an exclusive opportunity to own a turn-key modern 3200 sq ft home on three levels with a brand new sparkling pool, and cascading landscapes and stone walkways and patios. The interior flows seamlessly onto the expansive hilltop deck, creating the perfect setting for comfortable outdoor living and effortless entertaining. Whether enjoying quiet mornings overlooking the scenery or hosting guests against a stunning natural backdrop, this home offers an exceptional blend of luxury, comfort, and style. This amazing home is conveniently located to Breakwater Beach with deeded Creek access. Enjoy the wonderful Northfork lifestyle. *Some photos are virtually staged. --

1380 Jackson Landing, Mattituck
$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. The entry foyer opens to a formal living room or dining room, and a 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 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 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
$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
$1,590,000
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.

2340 Fairway Drive, Cutchogue
$649,000
4 Beds ⋅ 2 Baths ⋅ 1027216 MLS
Welcome to this exceptional North Fork opportunity. Resting on just over half an acre of level property in a quiet cul de sac, this ranch-style home offers four bedrooms, two bathrooms, a one car garage, nearly 1,800 square feet of living space, plus a full basement just under 1,600 square feet. Ideally situated in the heart of North Fork Wine Country, this home presents an excellent opportunity for buyers seeking an investment in the peace and tranquility offered by North Fork living. Enjoy easy access to Love Lane's shops, the Mattituck LIRR station, and nearby beaches including Veterans Beach, New Suffolk Beach, and Breakwater Beach. With a generous lot size in a sought after and desirable location, this as-is home is a canvas for endless potential to bring your North Fork vision to life.

685 Village Lane, Mattituck
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 1027212 MLS
Nestled in the heart of Cutchogue along a quiet private road, this beautifully maintained four-bedroom, two-and-a-half-bath home is set on more than 3.3 picturesque acres, graced by mature trees and thoughtfully landscaped grounds. Inside, hardwood floors, three gas fireplaces, Anderson windows, and two beautifully updated full bathrooms create warm, inviting living spaces designed for both everyday comfort and entertaining. The backyard embodies the best of North Fork living, featuring a new in-ground pool, spacious patio, outdoor bar, and mature landscaping—an inviting setting for relaxing or entertaining. A detached two-and-a-half-car garage with an expansive loft above offers flexible space for a home office, studio, workshop, or additional storage, while a barn-style outbuilding and expansive grounds provide exciting possibilities for equestrian use, hobby farming, or recreation. Just minutes from beautiful Peconic Bay beaches, wineries, farm stands, and some of the North Fork's best restaurants, this property offers the perfect balance of privacy and convenience. (Address also knows as 1 Banks St)

300 Private Road Unit #8, Cutchogue
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 1024349 MLS
Your North Fork Escape Awaits...Discover the charm of coastal living in this inviting Cutchogue retreat, ideally located just steps from the sandy shores of Peconic Bay Beach and around the corner from a marina. Whether you're searching for the perfect weekend getaway or a year-round haven, this special property offers the peaceful North Fork lifestyle you've been dreaming about. Enjoy seasonal water views, gentle bay breezes, and the tranquility of one of Cutchogue's most desirable beachside neighborhoods. The spacious main home features 4 bedrooms, 3 1/2 Bathrooms, an eat-in kitchen, living room, dining room, and a welcoming family room with a cozy wood-burning fireplace—perfect for gathering with friends. Additional conveniences include central air conditioning, oil heat, city water, central vacuum, an attached one-car garage, and a full basement. The property also features an exceptional Detached Two-car garage with an impressive bonus space above, offering endless possibilities for a home office, artist's studio, fitness room, recreation area, or the perfect place to pursue your favorite hobbies. The generous yard provides plenty of room for outdoor entertaining, lawn games, relaxing after a day at the beach, and even the potential for a future swimming pool. There are also two deeded access points to Little Creek just around the corner for launching kayaks, sailing, or mooring a small boat to cruise directly out to Peconic Bay. Located in the Cutchogue – New Suffolk Park District, you have numerous beach options, including free use of the “Nassau Point Community (“Causeway”) Beach just steps away from your front door. Whether you're boating, beachcombing, or simply unwinding in the quiet beauty of the North Fork, this property offers the ideal setting to create lasting memories with friends. Best of all, you'll enjoy low taxes, making this coastal getaway as practical as it is desirable. Come experience why this charming Cutchogue home could become your own private North Fork retreat. Whether you're looking for a peaceful weekend escape, a summer retreat, or a place to gather with friends year-round, this special property offers the perfect balance of comfort, charm, and coastal living. Spend your days enjoying nearby beaches, boating, championship golf courses, acclaimed vineyards, craft breweries, gourmet restaurants, farm stands, and all the beauty the North Fork is known for. With so much just moments away, you'll find yourself making memories here for years to come.

8275 Skunk Lane, Cutchogue
$659,000
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
$998,000
5 Beds ⋅ 4 Baths ⋅ 1012027 MLS
Welcome to 1520 Meday Avenue, a rare mid-century modern ranch built in 1977 and ideally located in the heart of Mattituck on Long Island’s coveted North Fork. Offering 5 bedrooms and 4 full bathrooms, this expansive residence combines classic architectural character with exceptional scale, privacy, and resort-style outdoor living. Designed around a striking central courtyard, the home is oriented to maximize natural light and views from nearly every room, creating a seamless connection between indoor and outdoor spaces. At the heart of the property lies a private in-ground pool, beautifully positioned within the courtyard and surrounded by a putting green—transforming the entire center of the home into a one-of-a-kind private retreat. Inside, the home features a spacious living room with fireplace, an open-concept kitchen, and a large dining room that together create an easy, flowing layout ideal for entertaining and everyday living. All bedrooms are generously sized, offering comfort, flexibility, and privacy for family and guests alike. While the home is well maintained and structurally sound, it presents an excellent opportunity for thoughtful updating—allowing a new owner to enhance and personalize a truly special architectural canvas while immediately enjoying its exceptional layout and setting. Located just minutes from Mattituck’s vineyards, farm stands, beaches, marinas, boutique shopping, and acclaimed restaurants, this property captures the very best of North Fork living. Whether envisioned as a year-round residence or a seasonal retreat, 1520 Meday Avenue offers a rare combination of space, design, and lifestyle in one of the region’s most desirable communities. A distinctive courtyard ranch with resort-style amenities, this is an opportunity to create something truly extraordinary.

1520 Meday Avenue, Mattituck
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 1015408 MLS
Nestled along picturesque Oregon Road, one of Cutchogue's most beloved country lanes, this beautifully restored farmhouse with a brand-new roof seamlessly blends timeless charm with modern comfort. Lovingly rebuilt in 2011 and thoughtfully maintained, this exceptional residence offers approximately 2,800 square feet of inviting living space on a half-acre parcel surrounded by the bucolic beauty of North Fork farmland. Rich in character, the home welcomes you with an original wood-beamed entry with a wood-burning stove that sets the tone for the warmth found throughout. Solid oak and country oak floors flow seamlessly from room to room. The three bedrooms, two and a half baths, along with the convenience of an elevator, whole-house generator, and three-zone heating system, are designed for effortless living and entertaining. The open-concept floor plan features a spacious living area with a wood-burning fireplace. and an expansive country kitchen, creating the perfect gathering place in every season. Step outside to your private backyard retreat, complete with a 14' x 26' heated saltwater swimming pool, ideal for relaxing summer afternoons or entertaining under the stars. Mature landscaping and miles of open farm views enhance the property's tranquil country setting. Located in the heart of Cutchogue's renowned wine country, surrounded by vineyards, farm stands, and some of the North Fork's most scenic landscapes, this special farmhouse offers a rare opportunity to enjoy the authentic charm and relaxed lifestyle that make Oregon Road such a treasured address.

10415 Oregon Road, Cutchogue
$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
$1,490,000
4 Beds ⋅ 3 Baths ⋅ 1018327 MLS
Nestled in the heart of the North Fork, this beautiful 4-bedroom, 2 1/2-bath Colonial offers the perfect blend of coastal charm and everyday convenience. Ideally situated near golf courses, pristine sandy beach, acclaimed restaurants, wineries, and the vibrant downtown area, this home provides an exceptional North Fork lifestyle. Inside, you'll find spacious living areas filled with natural light, generously sized bedrooms, central ac upstairs, and a thoughtfully designed layout perfect for both entertaining and comfortable family living. Step outside to your own private retreat featuring a large patio overlooking a beautifully landscaped backyard. The tranquil koi pond, elegant arbor, and lush gardens create a peaceful setting for outdoor dining, gatherings, or simply relaxing after a day at the beach or golf course. Whether you're seeking a year-round residence or a seasonal getaway, this charming Colonial offers the best of North Fork living in a highly desirable location.

1060 Case's Lane Ext, Cutchogue
$4,150,000
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
$995,000
4 Beds ⋅ 1 Baths ⋅ 1018515 MLS
North Fork- Cutchogue- Create your ideal North Fork retreat in an extraordinary natural setting. This single story, four-bedroom home sits along the tranquil edge of West Creek in Cutchogue, offering the rare potential for water views and a front row seat to the area’s ever changing local wildlife. Whether you envision a thoughtful renovation or a completely new design, the property provides a canvas in one of the North Fork's desirable locations. Down the road, a 10' wide neighborhood only right-of-way leads to a 33' portion of a Bay beach. Sweeping vistas make every visit unforgettable. The New Suffolk Beach is only moments from your doorstep, and the North Fork Country Club sits just steps away, adding to the exceptional lifestyle this setting affords.

240 Meadow Lane, Cutchogue
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 1016493 MLS
Location is everything. Privately set on 2.1 secluded acres, this stylish and charming farmhouse style home is approached by a long winding drive that reveals a striking 1,000-square-foot post-and-beam barn before opening to sweeping views of the property's picturesque grounds. Thoughtfully maintained and rich in character, the home offers a traditional floor plan complemented by hardwood flooring throughout and a substantial wood-burning fireplace that anchors the main living space. The kitchen has been tastefully updated with a gas range and generous peninsula seating, flowing seamlessly into a dining area overlooking the manicured landscape and seasonal water views beyond. Upstairs, four well-proportioned bedrooms include three guest bedrooms served by a full hall bath, while the sun-filled primary suite offers a private retreat overlooking the property, also offering those peek-a-boo winter water-views. A rare opportunity to enjoy privacy, acreage, and timeless North Fork charm in an exceptional setting w/ ample room an in-ground pool or equestrian activities. This is the country house on the North Fork you've searching for!

2700 Harbor Lane, Cutchogue
$2,850,000
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
$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
$1,950,000
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
$1,095,000
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
$795,000
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.

420 Sigsbee Road, Mattituck
$1,199,900
4 Beds ⋅ 3 Baths ⋅ 1008313 MLS
Nestled in the coveted Fleet’s Neck community of the North Fork, this beautifully renovated residence offers a thoughtfully designed layout with four bedrooms and three full bathrooms. Featuring two spacious primary suites located on opposite sides of the home, each with its own ensuite bathroom, the floor plan provides flexibility and privacy. The welcoming living room is centered around a wood-burning fireplace, creating a comfortable gathering space year-round. The professionally designed kitchen showcases quality finishes and craftsmanship, seamlessly connecting to the dining area for everyday living and entertaining. Recent improvements include new central air conditioning, natural gas heating and cooking, all-new white oak hardwood flooring throughout, custom moldings, and professionally designed bathrooms and kitchen spaces. Set on a picturesque property surrounded by mature trees, the home offers a peaceful setting with natural light filtering through the landscape. Blending modern updates with timeless appeal, this exceptional North Fork property offers a rare opportunity just moments from beaches, wineries, shopping, and dining.

675 Dicks Point Road, Cutchogue

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.