Cutchogue Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Cutchogue and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Listings in 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.

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.

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

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

$1,199,900

4 Beds ⋅ 3 Baths ⋅ 1008313 MLS

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

675 Dicks Point Road, Cutchogue

$1,450,000

4 Beds ⋅ 4 Baths ⋅ 1005646 MLS

Set on 3.4 private acres bordering preserved farmland, this four-bedroom, 3.5-bath home offers a compelling balance of privacy, space, and convenience, ideally positioned between the amenities of Mattituck and the beaches, marinas, and restaurants of New Suffolk. The semi-open floor plan is warm and functional, anchored by a substantial fireplace, vaulted ceilings, and hardwood floors that run throughout. The spacious first-floor primary suite features a beautifully renovated bath and oversized closet, while the eat-in kitchen, dining area, and guest bedroom complete the main level. A fully finished lower level significantly expands the living space, offering a large secondary living room, additional guest accommodations, and excellent storage. Outside, the new 14x40 deck creates an effortless extension of the home, perfectly suited for indoor-outdoor entertaining and relaxed North Fork living.

8579 New Suffolk Avenue, Cutchogue

Start Your Search

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.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.