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$5,100,000
5 Beds ⋅ 4 Baths ⋅ 991036 MLS
Waterfront Living, Surrounded By The Bay Perfectly positioned on the water with sweeping views in every direction, this 5-bedroom, 4-bathroom home offers a rare sense of being completely surrounded by the bay-almost as if you're floating on the water. Spanning 4,085 sq ft, the open floor plan is ideal for everyday living and entertaining. The home offers two outdoor spaces: a spacious patio just off the living room, ideal for dining and entertaining, and a waterside deck with a sandy area at the shoreline. Situated on nearly an acre, the property provides ample room for a pool. Oversized primary suite with attached office and custom closets. Generously sized bedrooms and a well-designed layout maximize space and light. A strong waterfront offering with excellent indoor-outdoor flow and expansive views. The photos are virtually staged.

7225 Nassau Point Road, Cutchogue
$3,850,000
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
$3,499,000
4 Beds ⋅ 3 Baths ⋅ 923175 MLS
Welcome to your private sanctuary on Long Island’s North Fork. This striking Mediterranean-inspired residence sits on over 2 acres of lush, water-front property, accessible only by driving through a working farm. Ensuring both exclusivity and a bucolic sense of arrival. As you approach, a winding drive sets the tone, with pastoral vistas and mature landscaping revealing the home gracefully perched near the water’s edge. The exterior features classic stucco and terracotta details that evoke timeless Mediterranean architecture. Step inside to a warm and inviting interior, where abundant natural light pours through expansive windows framing serene waterfront views. The main level offers an open living and dining area, ideal for both entertaining and daily living. One of the home’s standout assets is the finished lower level, perfect as a recreation hub, media room, or flexible living space to suit your lifestyle. Outside, the grounds are spectacular, sweeping lawns and multiple terraces lead you down toward the water’s edge. Whether enjoying morning coffee while listening to gentle lapping waves or hosting al fresco dinners under the stars, this property offers truly magical moments.

3400 Dignans Road, Cutchogue
$2,479,000
4 Beds ⋅ 5 Baths ⋅ 973930 MLS
Welcome to 675 Pine Tree Rd, a brand-new coastal retreat nestled on a half acre in Cutchogue. Enjoy the rare convenience of dropping your paddle board in creek at the end of the street, strolling around the corner to Broad Cove Marina or heading down the road to Causeway beach just .8 miles away. This beautifully crafted 4-bedroom 5-bathroom luxury residence offers 3,200 s.f. of thoughtfully designed living space flooded with light over size windows and high ceilings, elegant millwork and 3-1/2" white oak flooring throughout. The heart of the home is a stunning chef’s kitchen featuring quartz counter tops, custom cabinetry and Thermador appliances opening to the main living area, perfect for entertaining and enjoying the North Fork lifestyle. The home offers two primary suites, providing exceptional flexibility for owners and guests. A spacious first floor junior suite with cathedral ceiling offers comfort and privacy, while the second-floor primary suite features a tray ceiling, large walk-in shower, soaking tub and his/hers walk in closets. The second floor has a sitting area and two additional en-suite bedrooms with vaulted ceilings and walk in closets. Outdoors, beautiful lush landscaped grounds surround a saltwater heated pool and stone patio, ideal for summer gatherings and entertaining. A rare opportunity to own a brand new home in a premier location with completion expected in July 2026.

675 Pine Tree Road, 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
$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
$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
$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
$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 along with exclusive private beach rights to one of the North Fork’s fantastic stretches of shoreline. 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
$1,195,000
4 Beds ⋅ 2 Baths ⋅ 1033174 MLS
26905 Main Rd aka 115 Highland Rd. 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.

26905 Main Road, Cutchogue
$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
$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
$949,000
4 Beds ⋅ 3 Baths ⋅ 969684 MLS
Discover timeless charm and classic North Fork living in this stately 1910 Grand Dame, gracefully sited in one of Cutchogue’s desirable locations. Featuring four bedrooms and three well-proportioned floors, this distinguished home showcases a gambrel roof and period details that reflect a bygone era. Ideally situated just moments from the heart of Cutchogue village, you’ll enjoy easy access to local restaurants, shops, the library, and nearby beaches. Golf courses, vineyards, and award-winning wineries are all within minutes, offering the best of North Fork’s coastal lifestyle. This property backs up to the historic "The Old House - 1649" property, one of the original homes on the North Fork, providing both privacy and a sense of place steeped in local history. With generous living space, classic architectural lines, and a location that balances tranquility with convenience, this rare offering is perfect as a full-time residence or cherished weekend retreat. Come make your mark on a true North Fork classic.

630 New Suffolk 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.