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$1,995,000
4 Beds ⋅ 2 Baths ⋅ 973814 MLS
Sound Front Sunsets - the views from this 4 bed 2 bath house are unrivaled. Breathtaking sunsets over the Long Island Sound. On a quiet cul-de-sac, this house has several different living spaces, taking advantage of the views and opening out to the gracious backyard - ideal for entertaining or just relaxing while you watch the boats sail past or take in another dreamlike sunset.

795 Glen Court, Cutchogue
$1,649,000
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 strong values, 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
$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
$1,249,000
3 Beds ⋅ 3 Baths ⋅ 1040667 MLS
Welcome to this beautifully expanded three-bedroom, three-bath ranch set on a spacious .82-acre lot, in prime Mattituck location offering comfort, privacy, and an exceptional array of amenities. The home features an extra-large first floor primary en-suite bedroom with walk-in closet plus a junior en-suite bedroom, providing flexible accommodations for family and guests. Hardwood floors throughout and all of the bathrooms and kitchen have been recently updated. The eat-in kitchen is equipped with GE Profile stainless steel appliances and elegant quartzite countertops. The inviting living room or dining room, however you want to use it features a wood burning fireplace with insert, creating a warm and welcoming atmosphere. Relax in the heated and air-conditioned four-season sunroom, with radiant heat flooring which is also featured in all bathrooms. Central air conditioning provides additional comfort throughout the home. Large garage with epoxy floors, provides room for your vehicles and a workshop, extra storage and more. Outside, the property truly shines with a 20' x 40' heated saltwater in-ground pool, fully fenced for privacy and enjoyment. Two rear decks provide excellent spaces for outdoor dining and a 7 zone irrigation system. Additional features include owned solar panel system ensuring minimal electric bills, Suffolk County water and a whole-house water filtration system, as well as a full basement with 9' ceilings and Bilco doors, offering abundant storage and potential for additional living or recreational space. A rare combination of spacious grounds, resort-style outdoor living, and thoughtful interior amenities. Move right into this Mattituck gem!

235 Azalea Road, Mattituck
$799,000
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 secluded 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. A whole-house generator, fueled by a buried propane tank, 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
$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
$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
$1,775,000
4 Beds ⋅ 3 Baths ⋅ 1041373 MLS
Some second homes take a year of renovations before they’re ready to enjoy. This one is ready this weekend. Tucked into the sought-after Oasis at Mattituck, a private cul-de-sac community with no HOA, this nearly new 2023-built residence was designed for exactly this kind of life: fly in, unlock the door, and be poolside by dinner. Fully furnished and turnkey, there’s no waiting on deliveries, no decorating decisions, no contractor calls. Just show up. At approximately 3,600 square feet, the open-concept layout makes the most of every gathering, from morning coffee on the patio to long, lazy lunches and evenings that start at the pool and end around the fire pit. The heated saltwater pool and thoughtfully designed outdoor living space mean the world-class North Fork lifestyle starts the moment you arrive, not after weeks of getting the house guest-ready. For a second home, the math here works too: minimal maintenance thanks to newer, high-quality construction, no HOA fees eating into the budget, and a fully furnished setup that makes it just as easy to hand the keys to family or rent it out when you’re not using it yourself. Mattituck sits at the heart of the North Fork’s beaches, vineyards, farm stands, and restaurants - the version of Long Island people drive hours to visit for a weekend. Here, it’s just home. Whether this becomes a summer-only retreat, a year-round weekend escape, or eventually your full-time address, this is a rare chance to own a move-in-ready sanctuary in one of Mattituck’s most desirable communities without the wait.

3225 Stanley Road, Mattituck
$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 strong values and 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
$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
$925,000
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
$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
$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
$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
$1,425,000
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
$699,999
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
$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
$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 (finished) 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. This listing may include images that have been digitally altered or virtually staged.

2340 Fairway Drive, Cutchogue
$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
$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
$795,000
5 Beds ⋅ 4 Baths ⋅ 1012027 MLS
Huge Price adjustment! Bring your contractor and ideas - 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 on a shy half acre - originally 2 combined lots. 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. Property is being sold as-is and will require renovations and updating. 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
$749,000
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
$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
$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
$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

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