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$8,000,000
4 Beds ⋅ 6 Baths ⋅ 967500 MLS
Perched above the shimmering waters of Peconic Bay, this custom-built waterfront estate offers one of the North Fork's most coveted coastal settings. Tucked within the prestigious enclave of Nassau Point, the property commands sweeping panoramic bay views from nearly every room. Set on two lush landscaped acres with 200 feet of private bay beach, the 5,500-square-foot residence was designed with both elegance and ease in mind. Soaring ceilings and walls of glass draw the outdoors in, while an open-concept layout flows effortlessly from intimate family living to grand-scale entertaining. Two fireplaces add warmth and character, and a private home office speaks to the thoughtful functionality woven throughout. Four ensuite bedrooms and multiple waterside balconies provide hotel-caliber privacy guests. Outside, the grounds are nothing short of spectacular. A heated gunite pool, expansive bluestone hardscaping, and a covered waterside cabana create a resort-like environment steps from your own private beach. A finished walk-out basement rounds out the offering with a full bath, bar, and recreation room with direct pool access, ideal for summer entertaining. Opportunities where architectural integrity meets an irreplaceable natural setting are exceptionally rare on the North Fork.

3745 Nassau Point Road, Cutchogue

$4,725,000
7 Beds ⋅ 5 Baths ⋅ 934271 MLS
This stunning waterfront estate presents a unique opportunity to create a generational compound, complete with a boater's lifestyle, thanks to its private dock and ample outdoor entertaining space. Situated along the picturesque waters of East Creek, the property offers direct access and panoramic views of Peconic Bay, showcasing the lifestyle that is unique to the North Fork. The custom-built home features seven spacious bedrooms, including two primary en-suites, and five elegantly appointed bathrooms. The kitchen, which faces the waterfront, is designed for both functionality and scenic views, complete with a service entrance that makes hosting and entertaining a breeze. The generous layout prioritizes privacy and comfort, with a wall of windows that floods the space with natural light and offers stunning views. Outside, you’ll find a built-in kitchen elegantly situated under a wisteria pergola, which leads to beautifully landscaped terraced gardens. Additional highlights of the property include an office or bonus room, recreational space ideal for a gym or theater, outside access, and a custom bar. The two-car detached garage provides ample storage space in the loft, and there is room on the property to add a pool or tennis court. This estate is a must-see to fully appreciate its prime location and understated grandeur. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

4075 Stillwater Avenue, Cutchogue

$3,725,000
4 Beds ⋅ 3 Baths ⋅ 981891 MLS
Waterfront Serenity in Broadwaters Cove | Cutchogue - Tucked away in the coveted Broadwaters Cove enclave of Cutchogue, this exceptional waterfront retreat offers a rare blend of privacy, natural beauty, and effortless indoor-outdoor living. From the moment you arrive, the pace shifts-where open views of water signal the beginning of something quieter, calmer, and deeply restorative. Designed to embrace its surroundings, the home is filled with light and positioned to capture both sunrise and sunset, with sweeping water views from nearly every room. Nature is not just nearby-it's part of the experience. Protected coastal habitats invite an ever-changing backdrop of birdlife, from vibrant warblers to blue jays, creating a setting that feels both peaceful and alive. At the heart of the property is a thoughtfully designed waterfront lifestyle. A private dock with a de-icing system, expansive Ipe decking, an outdoor shower, and room for a pool create a seamless connection to the water. Whether enjoying morning coffee as the sun rises or unwinding at dusk, every detail supports relaxed, open-air living. Inside, the home blends comfort with craftsmanship. A serene, coastal-inspired palette sets the tone, complemented by radiant heated floors and smart home technology for efficient, remote management. The flexible layout includes generous living spaces and a gourmet kitchen with abundant storage, ideal for both everyday living and entertaining. A fully insulated attic offers exceptional additional space, perfect for storage, a studio, or workspace. Across every season, the property offers a distinct kind of beauty. Spring awakens the landscape with color and renewal. Summer brings blooming crepe myrtles and lavender-framed outdoor spaces perfect for gatherings. Fall introduces rich foliage and cozy moments indoors. Winter transforms the home into a peaceful retreat, complete with fireside evenings. Close to North Fork award winning vineyards, renowned restaurants, boating, farmstands and great shopping. A place to gather, recharge, and create lasting memories, this waterfront offering is as inviting as it is timeless. Could be you!

1940 Mason Drive, Cutchogue

$2,750,000
4 Beds ⋅ 3 Baths ⋅ 1001609 MLS
Welcome to Nassau Point, an iconic community in the heart of the North Fork. This serene waterfront home features a private dock and an exquisite pool, situated on Broadwater's Cove with direct access to Peconic Bay. Homeowners in this community enjoy private access to the sandy causeway beach and the point sandbar. Upon entry, you are welcomed by a spacious foyer that leads you either to the kitchen and entertaining space or down the hallway that opens to the bedrooms. This waterfront residence boasts four bedrooms, including a spacious primary suite with its own access to the waterside deck. The junior bedroom also has deck access and shares a bathroom with the third bedroom, which is located in a separate wing. The fourth bedroom, offering water views, can easily be converted into a home office or bonus space. The generously sized enclosed sunroom faces the cove, capturing stunning views and providing access to the wraparound deck. The renovated kitchen is well-appointed with a coastal palette, and the dining area features built-in window seating. The living room, equipped with a wood-burning fireplace, is designed for entertaining, boasting high ceilings and views that create a resort-like atmosphere. Outdoors, you'll find a beautiful new pool surrounded by terraced landscaping and a lounge patio, offering ample space for relaxation and entertainment. The home is also equipped with a generator and features a single detached garage. Conveniently located near all that the North Fork has to offer—wineries, beaches, shopping, and farm stands—this property offers privacy and exclusivity for the discerning buyer.

580 Broadwaters Road, Cutchogue

$2,000,000
967470 MLS
DORSET FARMS - OREGON ROAD An exceptional North Fork opportunity with scale, pedigree, and a clear path forward. 4100 Oregon Road spans approximately 33 acres in the heart of Cutchogue, combining established viticulture with a rare, rights-retained parcel on a prime stretch of Oregon Road. The estate includes approximately 31 acres with development rights sold to the Town of Southold (preserved), plus 2 acres with retained rights. The rights-retained parcel measures approximately 200'x400' and fronts Oregon Road-an ideal setting for a high-visibility retail tasting room concept and/or a private residential build. A substantial vineyard footprint is already in place, with approximately 24.3 acres planted across key varietals: Chardonnay (10.4 acres), Cabernet (4 acres), Merlot (3.75 acres), Sauvignon Blanc (2.2 acres), Pinot Gris (2.2 acres), Petit Verdot (.75 acre), and Malbec (1 acre). The grapes from these vineyards have historically been used exclusively to make wine at Lenz Winery in nearby Peconic, with those wines consistently acclaimed by leading wine industry professionals such as Robert Parker's 'The Wine Advocate'. Supporting infrastructure includes deep irrigation well (recently refitted), partial irrigation lines in the vineyard, deer fencing, irrigation mains/tubing, and bird netting. A large barn offers on-site storage for equipment and vineyard nets (in need of repair). Dorset Farms is available to provide vineyard management for one to two years post-closing at commercial rates (approximately $8,000 per vineyard acre) and select vineyard management equipment may be available separately. This is a compelling offering for a buyer seeking a true North Fork footprint-preserved acreage, established plantings, and the flexibility of a road-front rights-retained parcel to bring a vision to life.

4100 Oregon Road, Cutchogue

$1,785,000
5 Beds ⋅ 4 Baths ⋅ 909841 MLS
Set against the backdrop of the stunning North Fork, this brand-new luxury home in Cutchogue offers the perfect mix of sophisticated design and laid-back coastal living. Just minutes from renowned wineries, farm-to-table restaurants, and some of Long Island’s most beautiful beaches, this 5-bedroom, 4-bathroom gem invites you to enjoy the best of both worlds. The heart of the home is the expansive great room, where large windows flood the space with natural light, creating a warm and inviting atmosphere. This open layout flows seamlessly into a spacious dining area and a chef’s kitchen—a true focal point of the home. With a large center island, custom cabinetry, and quartz countertops, it’s a perfect place for both everyday meals and entertaining guests. This beautiful brand-new home offers modern luxury and peace of mind with thoughtful features throughout. Enjoy elegant landscape lighting that highlights the property’s beauty day and night, a state-of-the-art alarm system for added security, and Ring cameras strategically placed around the home for complete protection and convenience. Inside, custom-designed closets provide style and organization in every room. The first-floor primary suite offers a serene retreat, with a spa-inspired bathroom that includes a soaking tub and a rain shower, as well as ample closet space for ultimate convenience. The thoughtful design and attention to detail are evident throughout, from the elegant oak hardwood floors to the custom tile work in the bathrooms. Outside, the home is beautifully surrounded by lush, manicured landscaping, offering the ideal setting for outdoor entertaining or simply relaxing on the front or back porch. Whether you’re enjoying the local wine country or unwinding in your private sanctuary, this home provides the perfect space to do it all. With its perfect blend of luxury, location, and lifestyle, this Cutchogue beauty is ready to welcome its new owner. Don’t miss the chance to experience a new level of comfort and sophistication on the North Fork. Whether you're hosting guests or seeking a peaceful escape, this home delivers timeless design, high-end craftsmanship, and unbeatable access to all that makes the North Fork a premier destination. Pool permit document available upon request. By appointment only. This is new construction - Tax Rates are still being formulated for 2026. 2026 taxes are estimated to be 10,500. All info is deemed reliable but not guaranteed and should be independently verified by the buyer.

5675 Bridge Lane, Cutchogue

$1,625,000
5 Beds ⋅ 3 Baths ⋅ 1016561 MLS
Welcome to 145 Baldwin Place, a spacious and inviting 5 bedroom Colonial set on two private acres in the heart of Cutchogue. A sun-filled foyer with cathedral ceilings creates an impressive first impression, leading to thoughtfully designed spacious living spaces ideal for both everyday living and entertaining. The center of the home is the expansive open concept kitchen with a seamless flow into living and dining areas. Upstairs, the private primary suite serves as a true retreat with vaulted ceilings, generous closet space and a spacious ensuite bathroom. Four additional bedrooms provide generous space and flexibility throughout the home. Set on two private acres, the property offers a beautifully landscaped setting along with plenty of open space for recreation, a pool or outdoor entertaining. Located just moments from the pristine beaches of the Peconic Bay, residents can enjoy swimming, kayaking, paddleboarding, and unforgettable sunsets. Nearby farmstands, vineyards, waterfront dining, and charming village shops complete the quintessential North Fork lifestyle. Whether you are seeking year round residence or a weekend escape, this home offers space, privacy and the best of North Fork living.

145 Baldwin Place, Cutchogue

$1,625,000
4 Beds ⋅ 3 Baths ⋅ 969968 MLS
Welcome to this exquisitely renovated home nestled in the highly sought-after Fleets Neck community, thoughtfully transformed to blend modern elegance with luxurious comfort. Constructed with steel beam framing and enhanced by an insulated basement, oversized Andersen windows and sliders, and beautiful mahogany decking, the residence offers exceptional quality throughout. A large, sun-filled living room showcases a dramatic cathedral ceiling and inviting wood-burning fireplace, while the stunning chef’s kitchen features top-of-the-line Thermador appliances, a stylish backsplash, center island, and striking 2.5-inch quartzite countertops, flowing seamlessly into the dining area for effortless entertaining. The serene primary suite impresses with a tray ceiling, cozy sitting area, spa-inspired bath with dual vanities, glass shower, soaking tub, and generous walk-in closets. Additional highlights include radiant heat in the bathrooms, well-appointed guest bedrooms, a first-level guest room with a second wood-burning fireplace, and a lush grassy lawn with an expansive wrap-around deck ideal for outdoor gatherings, with ample space to add a pool. Ideally located near a private beach, Park Beach, and the local marina, this exceptional property offers the perfect lifestyle for both beach lovers and boating enthusiasts. Pool Permit is in place for a 20 X 42 gunite pool.

480 Eastwood Drive, Cutchogue

$1,605,000
4 Beds ⋅ 3 Baths ⋅ 991067 MLS
Here’s what I love about 2120 Crown Land Lane in Cutchogue. The first thing that stood out to me was the setting. Across the street, you have this beautiful stretch of woods that will not be built on, and it gives the front porch such a calm, private feeling. Sitting there in the evening, catching the sunset over that side of the neighborhood, you immediately understand why this house feels different. The approach is also beautifully done. The driveway is finished with Belgian block edging, the walkways to the front and back of the home have landscape lighting, and the evergreens along the property create this polished, private view of the house and backyard. It feels manicured, but not stiff. Then you get to the backyard, and honestly, this is where the house really shows off. The grilling pavilion is fantastic, but the fire pit area is one of the best conversation spaces I have seen. A radius-cut floating bluestone bench wraps around individual seating areas and a 4-foot fire pit, all set on a bluestone patio and anchored by a stunning magnolia tree. Just beyond that, there is a bocce ball court, the pool area, and another outdoor room that makes the whole backyard feel like a private resort. What makes it even better is that all of these outdoor spaces have speakers and lighting, so whether it is a quiet night by the fire or a full summer gathering, the atmosphere is already built in. Inside, the kitchen is exactly what you hope to find. Thermador appliances, a 4-burner gas cooktop with griddle, beverage drawers, wine storage, double ovens, microwave, and this incredible shade of blue on the island and cabinetry that gives the space personality without feeling trendy. It is custom, useful, and beautiful all at once. The home also has speakers in the kitchen, den, and living room with fireplace, along with Lutron smart home lighting, which makes entertaining feel easy. The bathrooms are beautifully updated with tile selections that feel current, but timeless. Add in access to amazing sandy beaches in the Cutchogue Park District, the library, school, diner, and easy access to the Hampton Jitney for NYC, and this home starts to make a lot of sense. It has so many of the features people are looking for in new construction, but without the new construction price tag. That is why I love it.

2120 Crown Land Lane, Cutchogue

$1,470,000
3 Beds ⋅ 2 Baths ⋅ 964173 MLS
Located in the prestigious Nassau Point community, this three-bedroom, three-bath first-time-on-the-market home, set on just shy of three-quarters of an acre, has been meticulously curated and lovingly maintained. The first floor features a spacious primary bedroom suite, along with an additional bedroom and full bath - perfect for guests or single-level living. Upstairs, you’ll find a private third bedroom and bonus space, offering separation and versatility. Inside, soaring cathedral ceilings elevate the dramatic family room, anchored by an impressive oversized fireplace that serves as a stunning focal point and natural gathering space which meanders into the formal dining room and chefs’ kitchen with top-of-the-line stainless appliances. Expansive outdoor living is equally compelling, highlighted by a covered deck crafted from Brazilian hardwood, a charming shed and lush garden - an elegant setting for entertaining or quiet relaxation overlooking the beautifully maintained grounds. Room for a pool. A full-footprint basement with 9-foot ceilings offers exceptional potential for future expansion, recreation space, or substantial storage. Blending timeless coastal charm, thoughtful design, and an unparalleled setting, this is a rare opportunity to own a refined sanctuary in one of the North Fork’s most desirable and exclusive enclaves. Enjoy access to two private bay beaches and rights-of-way providing water access to residents throughout the peninsula, along with the opportunity to join the community association.

2150 Haywaters Road, Cutchogue

$1,440,000
4 Beds ⋅ 2 Baths ⋅ 981841 MLS
Tucked within the coveted Fleets Neck community, this charming Cape Cod–style home offers a seamless blend of indoor comfort and effortless outdoor living, all set in the heart of the North Fork’s celebrated farm and wine country. Perfectly positioned just moments from local vineyards, farmstands, and bay beaches, the location alone captures the essence of the North Fork lifestyle. Designed with entertaining in mind, the home features an updated, open-concept layout anchored by a striking stack stone wood-burning fireplace in the great room—an inviting space for gathering year-round. Just beyond, a formal dining room with soaring ceilings overlooks the backyard, where the true highlight of the property unfolds. Step outside to a private, resort-like setting centered around the in-ground pool, surrounded by an expansive patio and dedicated outdoor grilling area—ideal for summer afternoons that stretch into evening dinners under the open sky. Whether hosting large gatherings or enjoying quiet weekends at home, the outdoor living experience here is both functional and beautifully integrated. The main level offers two generously sized bedrooms and an updated full bathroom, while the second floor features two additional guest bedrooms and another updated full bath, providing comfortable accommodations for all. As part of the Fleets Neck Association, residents enjoy exclusive access to a private beach overlooking Cutchogue Harbor, with sweeping views toward Robins Island and Nassau Point—an idyllic extension of this already exceptional setting.

350 Eastwood Drive, Cutchogue

$1,285,000
3 Beds ⋅ 2 Baths ⋅ 958993 MLS
Artist/Designer Inspired Modern No Fork Living w Enduring Views: Unique property enjoying uninterrupted farm views both across the street and from the backyard—protected open land that ensures long-term privacy, open skies, breathtaking sunsets and sunrises with open space views that will remain. A welcoming front porch invites slow mornings and quiet evenings, while the home’s thoughtful indoor–outdoor design connects daily life seamlessly to the landscape. This newly renovated single story 3 bedroom, 2 bath ranch with cathedral ceilings is a blend of updated conveniences with attention to detail finishing from pot fillers in the kitchen to Italian Glass and Handmade Ceramic Tiles in the Kitchen and Bathroom. Seamless management, open floor plan flanked with private spaces and North Fork views makes this a rare North Fork gem capturing the soul of its' authentic beginnings with its beloved contemporary lifestyle. A primary en-suite featuring a wall of glass doors opening to a private deck overlooks open fields and sunset skies. A secondary deck off the kitchen creates the perfect setting for relaxing after a long day at the beach, followed by enjoying an outdoor shower, alfresco dining, entertaining, and lingering evenings outdoors around the fire pit. Experience organic fruit juices pressed with your own press in your backyard from the apple, pear, peach fruit trees that flank the parameter your very own backyard offering seasonal harvests and a natural sense of enclosure that reflects the North Fork’s agricultural heritage. The North Fork’s temperate, coastal climate supports a lifestyle that feels balanced with—warm summers moderated by breezes, long luminous falls, quiet restorative winters, and gentle springs that invite outdoor living to return naturally. Days here are shaped by light, land, and season rather than schedules. Enjoy working at home part or full time in the second bedroom/office with built in digital workstations or during the warmer months in the accessory Art Studio with expansive views. A truly special property complete just as is but comes with endless options to add space, a pool, and or capture interior space in the basement and create a Rec Room, Media Room, etc. Just moments away, enjoy access to a renowned vineyard’s tasting room and an organic farmstand and market—where fresh harvests, local wines, and authentic farm life become part of everyday living. Miles of preserved farmland and nearby beaches offer space, calm, and perspective rarely found so close to the city. Ideal as a refined weekend retreat, a sophisticated part-time residence, or a full-time home, this offering speaks to buyers who value access without effort, nature without isolation, and luxury defined by permanence rather than excess. A setting defined by protected land, enduring views, and a position that will never change.

5845 E Bridge Lane NE, Cutchogue

$1,085,000
5 Beds ⋅ 4 Baths ⋅ 956761 MLS
Discover this inviting five-bedroom colonial located in the highly desirable Fleets Neck beach community of Cutchogue. Designed with comfort and space in mind, this home is ideal for hosting extended family and guests. The first floor offers a warm and welcoming layout, featuring a living room with a cozy wood-burning fireplace that opens to a bright family room with sliders leading to the rear deck. The spacious first-floor primary suite includes its own sitting area or office, providing a private retreat. An open-concept kitchen with a charming breakfast nook, a formal dining room, and a powder room complete the main level. Upstairs, you’ll find four generous guest bedrooms—one with its own half bath—along with a hall bath. Perfect for year-round or seasonal living, this home is just moments from two sandy bay beaches, a marina, and a local park. For those seeking an authentic North Fork lifestyle, this property truly delivers. Restaurants, shops, farm stands, wineries, breweries, boating—everything that makes the area special is right at your fingertips.

275 Pinewood Road, Cutchogue

$965,000
3 Beds ⋅ 2 Baths ⋅ 972197 MLS
Welcome to Fleet’s Neck—one of Cutchogue’s most coveted coastal enclaves—where 5050 Pequash Avenue (Rosner House) 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 3-bedroom, 2-bath residence with CAC and new water heater, is ideally positioned on a beautiful property. A highly desirable layout includes a ground-floor bedroom, while additional bedrooms provide ample space for entertaining. Open floor plan with spacious living room with fireplace, wide plank wood floors and dining room. 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 all that makes the North Fork so 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, 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.

5050 Pequash Avenue, Cutchogue

$920,000
3 Beds ⋅ 3 Baths ⋅ 1020932 MLS
Welcome to 2725 Skunk Lane, a beautiful home nestled in the heart of Cutchogue NY. This 1950s build seamlessly blends vintage charm with modern conveniences, ensuring a comfortable, unique living experience. There are three spacious bedrooms, 2.5 bathrooms, a sunroom, and a versatile office space, this home is designed with functionality in mind. The main floor hosts a generous suite complete with a renovated full bathroom, offering a private retreat within the home. The heart of this residence is undoubtedly the bright eat-in kitchen, well-equipped with ample cabinetry and a pantry. The adjacent living and dining areas provide the perfect backdrop for both casual meals and formal gatherings. Outside, the beautifully landscaped yard, there is plenty of room for a pool. Additionally, this property includes a large two-car garage, providing plenty of storage and parking space. The location of this home is hard to beat. Just over a mile from Nassau Point beach and Indian Neck Beach and boat ramp, this property allows you to enjoy the coastal lifestyle at your leisure. Also, this home is nearby many wineries, restaurants, recreational parks, and shops. This home is the perfect spot to enjoy the North Fork.

2725 Skunk Lane, Cutchogue

$861,000
4 Beds ⋅ 2 Baths ⋅ 943582 MLS
Fantastic income opportunity awaits South of Main less than a mile from the beach! North Fork charmer includes both a 3 bedroom main house and a separate 1 bedroom accessory apartment over the garage. The main house on Pequash is a 3 bedroom farmhouse style colonial which welcomes you inside with its covered front porch. Interior features include hardwood floors, quartz counters in the open kitchen plus large pantry, central air and loads of storage in the full basement. On the same property facing Willow Street is a completely separate one bedroom 800 square foot accessory apartment located above the detached 2 car garage providing great potential rental income for an owner occupant. Located in the heart of all the best that Cutchogue and the North Fork have to offer... close to beaches, vineyards, farmstands, shops and dining.

1125 Pequash Avenue, Cutchogue

$630,000
4 Beds ⋅ 2 Baths ⋅ 941132 MLS
This is the farmhouse fixer-upper you’ve been waiting for! Located in the heart of Cutchogue, this 4-bedroom, 1.5-bath home sits on over half an acre of fully fenced, picturesque property and offers endless potential. The private fully fenced backyard features mature trees, a serene koi pond, and a covered deck—perfect for creating your own outdoor retreat. A 600 sqft detached garage provides ideal space for a workshop, studio, or storage for a tradesperson. The first floor offers an open living room, kitchen, dining room, and half bath. Upstairs, you’ll find four generously sized bedrooms showcasing original trim work and hardwood floors throughout. Partial basement has interior and exterior access, as well as a walk-up attic. Ready for updating, this home is a great opportunity to personalize and add value! With its prime location and strong potential for appreciation, this property is ideal for buyers looking to invest in one of Long Island’s most desirable communities. A must-see to truly imagine the possibilities! Will require rehab, construction loan or cash.

4300 Depot Lane, 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.