Cutchogue Homes with Mattituck-Cutchogue Elementary Sch Elementary school

Welcome to Cutchogue, a picturesque hamlet nestled in the heart of Long Island’s North Fork, New York. Renowned for its stunning vineyards, charming waterfront views, and a tight-knit community, Cutchogue offers a tranquil escape from the hustle and bustle of city life. Here, you can enjoy the best of both worlds—serene rural landscapes and proximity to vibrant local culture.

Cutchogue is not just a beautiful place to live; it’s also a family-friendly haven. The community is served by the highly regarded Mattituck-Cutchogue Elementary School, which is dedicated to fostering a supportive and enriching learning environment for children. With a strong emphasis on academic excellence and personal growth, this school is a cornerstone of the community, making homes in Cutchogue particularly appealing to families seeking quality education for their children.

Real estate in Cutchogue showcases a delightful mix of charming cottages, modern family homes, and luxurious waterfront properties, all set against the backdrop of lush vineyards and serene landscapes. Whether you’re looking for a cozy retreat or a spacious family home, Cutchogue has something to offer everyone.

As you explore this enchanting hamlet, you’ll discover a community that values connection, education, and the joys of nature. With its welcoming atmosphere and beautiful surroundings, Cutchogue is not just a place to live; it’s a place to thrive. Come and experience the charm of Cutchogue—where your dream home awaits!

Newest Cutchogue Homes with Mattituck-Cutchogue Elementary Sch Elementary school

$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

$1,799,000

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

$1,425,000

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

$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

$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

$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

$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

$995,000

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

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