Cutchogue Real Estate

Welcome to Cutchogue, a charming hamlet nestled in the heart of New York's picturesque North Fork of Long Island. Known for its stunning landscapes, rich agricultural heritage, and inviting community, Cutchogue offers a unique blend of rural tranquility and coastal charm.

Cutchogue is renowned for its lush vineyards and wineries, making it a delightful destination for wine enthusiasts and food lovers alike. With its fertile soil and temperate climate, the region produces some of the finest wines in the country. Visitors can spend leisurely afternoons touring local vineyards, enjoying tastings, and savoring gourmet meals crafted from fresh, locally sourced ingredients.

Beyond its wine country, Cutchogue boasts beautiful beaches and serene waterfronts, perfect for those seeking a peaceful escape. The nearby Long Island Sound provides ample opportunities for boating, fishing, and swimming, while the scenic landscapes invite outdoor activities like hiking and biking. The area is also home to charming boutiques, farm stands, and artisanal shops, where you can find unique treasures and support local artisans.

Cutchogue's strong sense of community is evident in its annual events and gatherings, where residents come together to celebrate their shared love for this idyllic hamlet. The friendly atmosphere, combined with the area's natural beauty, makes Cutchogue a wonderful place to call home or a perfect getaway destination.

Whether you’re looking to invest in a quaint cottage, a sprawling estate, or simply explore the wonders of this hidden gem, Cutchogue offers a truly enchanting experience. Come discover the charm and beauty of Cutchogue, where every day feels like a vacation!

Newest Listings in Cutchogue

$625,000

1055110 MLS

Zoned Limited Business. Bring your vision. Rare opportunity allowing for many options to custom build or redevelop this property into what you need to optimize your current or future North Fork business and your life. Retail, workshop, office, restaurant, repairs, B&B, pet care, private warehouse, childcare, single family or 2-family owner occupied are all listed uses under LB zoning (site plan approval needed). See Southold Town website for full LB zoning information. No representation made on condition of existing structures including main structure or outbuilding.

37200 Main Road, Cutchogue

$1,595,000

4 Beds ⋅ 2 Baths ⋅ 1053905 MLS

MIAMI MODERNISM MEETS THE NORTH FORK. Set on a spacious and private .60-acre hilltop parcel in coveted Nassau Point, this fully updated four-bedroom modernist ranch offers an unexpected departure from the ordinary. Its traditional exterior gives little indication of the sleek, light-filled interiors within—an independently conceived home with the confident glamour of Miami and the relaxed ease of Cutchogue. Individual design matters. Rather than repeating a familiar, cookie-cutter floor plan, this residence has an architectural identity all its own, expressed through gleaming white marble floors, clean lines, generously proportioned rooms and a seamless connection between indoor and outdoor living. The result feels distinctive, sophisticated and refreshingly personal. At the heart of the home is a spectacular chef’s kitchen designed for serious cooking and effortless entertaining. It opens to a private garden courtyard, creating an intimate setting for morning coffee, outdoor dining or summer evenings with friends, and an ideal location for a future pool. A comfortable den with fireplace leads to more than 600 square feet of decking, while the bright formal living and dining rooms provide gracious spaces for larger gatherings. Nearly 2,000 square feet of living space includes four bedrooms offering exceptional flexibility for overnight guests, working from home, fitness or creative pursuits. The expansive primary suite is a private retreat with a dedicated office area, large walk-in closet and sparkling marble bath. A guest bath and separate laundry room complete the main level, while the finished lower level provides valuable additional space for recreation, media or hobbies. An oversized two-car garage offers generous parking and storage. Just up the road from sublime Fisherman’s Beach, the property enjoys access to Nassau Point’s rights-of-way beaches and nearby Causeway Beach on the Peconic Bay. Spend the day swimming, kayaking, paddleboarding or boating, then return home for cocktails on the deck or dinner in the garden courtyard. Causeway Beach also offers a designated swimming area, summer lifeguards, picnic facilities, playground equipment, a basketball court and restrooms. This sought-after Cutchogue location places vineyards, farm stands, celebrated restaurants, local shops and the villages of the North Fork within easy reach. Private but never isolated, stylish without being conventional, this is a rare opportunity to experience the Nassau Point lifestyle in a home with a point of view all its own.

1000 Haywaters Road, Cutchogue

$649,000

2 Beds ⋅ 1 Baths ⋅ 1053686 MLS

Charming 2-bedroom, 1-bath home in desirable Cutchogue, featuring an attached 2-car garage and room for a pool. A wonderful opportunity to make it your own, with potential to expand, upgrade, and design to suit your vision. Close to restaurants, beaches, and North Fork vineyards.

995 Schoolhouse Road, Cutchogue

$4,750,000

6 Beds ⋅ 9 Baths ⋅ 1051114 MLS

Set on nearly two private acres in Nassau Point, this brand-new, 8,500+ square-foot residence offers three levels of thoughtfully designed living space, just minutes from the North Fork’s finest beaches, vineyards, and farm stands. Inside, 10-foot ceilings and herringbone oak floors set an elegant tone from the moment of entry, while a wall of glass frames views of the stone patio beyond. The chef’s kitchen serves as a striking centerpiece, appointed with Sub-Zero and Wolf appliances, a 9-foot island, dual dishwashers, three wine refrigerators, and a hidden walk-in pantry. The space flows seamlessly into an open dining area and expansive great room anchored by a gas fireplace and floor-to-ceiling glass doors opening to more than 1,000 square feet of patio space. Six en-suite bedrooms with radiant-heated baths include two primary suites: one on the main level for convenient single-level living and a second upstairs featuring a spa-like bath and private 400-square-foot terrace. Designed for both entertaining and relaxation, the walk-out lower level features an interior cabana with a recreation room, wet bar, gym, sauna, and flexible bonus space ideal for a theater or wine cellar. Outdoors, a saltwater pool, outdoor shower, and room for a tennis court create a private resort-like setting. A whole-house generator, oversized walk-up attic, and three-car garage complete the residence. A rare combination of scale, quality, privacy, and location on the North Fork.

3360 Wunneweta Road, Cutchogue

$950,000

3 Beds ⋅ 2 Baths ⋅ 1051628 MLS

This, just perfect, 3-bedroom 1.5 bath ranch sits nicely on a beautiful corner lot at just shy of 1 acre. You are welcomed home with a sweet front porch and then enter the front door to a beautiful open floor plan, including a granite and stainless-steel custom kitchen, dining room and living room. The primary bedroom has its own private door to the deck and a half bathroom. There are 2 additional bedrooms and the main bathroom is only 2 years old. Feel a cool North Fork breeze in the home with the front windows up and the rear sliding glass door slid open to the beautiful, entertaining back yard. Summers can be spent lounging on the patio around an in ground pool, BBQ’s on the deck or just reading a fabulous book in your private and peaceful surroundings. Enjoy all the North Fork of Long Island has to offer! Being within minutes of fabulous wineries, restaurants, beaches, farmstands, shopping and Cutchogue Village. You’ll find this home and its location to be perfect for year-round living or that warm home away from home.

985 Silver Colt Road, Cutchogue

$1,150,000

3 Beds ⋅ 2 Baths ⋅ 1039271 MLS

Charming Oregon Road1800's Farmhouse with Sweeping Bucolic Views and year round stunning sunsets. Experience country living at its finest in this beautifully maintained farmhouse overlooking scenic agricultural farmland. This inviting home features 3 bedrooms and 2 full baths, blending historic charm with peaceful rural surroundings. Enjoy breathtaking views, open skies, and the tranquility of farm country while being within easy reach of local amenities. Full basement, 1 car garage, storage shed.

13700 Oregon Road, Cutchogue

$3,300,000

5 Beds ⋅ 6 Baths ⋅ 1028703 MLS

Introducing Bay Breeze Veranda, a one-of-a-kind luxury custom build set within a coveted coastal enclave in one of the North Fork’s most desirable and high-value communities. Privately positioned on a shy one-acre corner lot in Cutchogue, this exceptional 5-bedroom, 6-bath residence captures the essence of refined coastal living with extraordinary attention to craftsmanship, scale, and design. From the moment you arrive, Bay Breeze Veranda makes a statement. Thoughtfully conceived for both sophisticated entertaining and effortless everyday living, the home blends timeless architectural character with elevated modern amenities and an unmistakable sense of place. The spacious interiors are filled with natural light and designed to create a seamless connection between indoors and out. Generous living spaces, beautifully appointed finishes, and custom details throughout reflect the quality and individuality of this exceptional residence. At the heart of the home, an upscale chef kitchen featuring custom cabinets, high-end appliances, quartz countertops and wine bar. Dramatic great room with custom stone fireplace. Luxurious first floor primary suite with ensuite bath and private access to a patio and backyard. An entry foyer, formal dining room, living room, laundry room and powder bathroom complete the first floor. Upstairs an additional 4 en-suite bedrooms provide comfort and privacy, while the 4 beautifully designed baths elevate the experience with a sense of understated luxury. Separate attic and storage space. Outside, the property becomes a private resort. A stunning in-ground swimming pool anchors the grounds, creating an idyllic setting for long summer afternoons, poolside entertaining, and quiet evenings beneath the stars. The shy one-acre corner parcel provides a rare combination of privacy, presence, and usable outdoor space. Ample room for a pool house or garden shed. Oversized 2 car garage and the lower level offers additional living space and can be finished to suit. Set within a highly sought-after coastal enclave, Bay Breeze Veranda is ideally positioned walking distance to the best Peconic Bay beaches and a marina, offering easy access to boating, swimming, fishing, paddle boarding, and the quintessential North Fork waterfront lifestyle. The surrounding area is celebrated for its beaches, vineyards, farm stands, restaurants, and charming village communities. Just 90 miles from New York City, and Hampton Jitney stops in Cutchogue. This is more than a custom home—it is a rare opportunity to own a truly distinctive property in one of the North Fork’s most coveted coastal settings. Bay Breeze Veranda — where custom luxury meets the coast. Unique, higher end custom home with spacious corner lot and privacy. To be built for 2027. Located on Dartmouth Place, off of 2105 Pequash.

2105 Pequash Avenue, Cutchogue

$2,395,000

4 Beds ⋅ 4 Baths ⋅ 1041399 MLS

Set within the coveted enclave of Nassau Point, this exceptional 4,000-square-foot retreat offers privacy, timeless architecture, and an elevated North Fork lifestyle. Positioned on a shy acre with plenty of room for a pool, this beautifully designed home is crafted for effortless year-round living and entertaining. A dramatic Great Room with cathedral ceilings and wood floors anchors the residence, complemented by a chef’s kitchen, den, reading room, game room with wet bar, billiard room, wine cellar, and private second-floor primary suite with office. The home’s generous and versatile layout offers exceptional flexibility for separate guest quarters, extended living arrangements, or the potential for an owner-occupied accessory rental, subject to all applicable municipal approvals and permitting. Wraparound decks, lush gardens, a four-car garage, and full-house generator complete the property. Just moments from the Peconic Bay, residents enjoy access to private bay beaches and rights-of-way throughout the peninsula, with the opportunity to join the voluntary property owners association. A rare opportunity to own a refined private sanctuary in one of the North Fork’s most desirable communities.

3980 Vanston Road, Cutchogue

$1,425,000

3 Beds ⋅ 3 Baths ⋅ 1045590 MLS

Fully renovated in 2018, this spacious ranch offers more than 2,600 square feet of comfortable, flexible living space and enjoys bucolic views across surrounding vineyard and farmland beyond. Located in a private neighborhood in the heart of Cutchogue, the property spans 0.70 acres with a serene pool, outdoor patio, custom exterior fire pit, with private community beach access is just a few hundred yards away. The home's generous proportions and easy layout lend themselves equally well to everyday living and entertaining, with vaulted ceilings, charm and personality that elevate a classic ranch. Thoughtfully updated and entirely move-in ready, it offers an appealing combination of space, convenience, and quintessential North Fork surroundings. Perfectly positioned in the center of the region, the property is just minutes from Sang Lee Farms, 8 Hands Farm, Love Lane, local vineyards, and many of the area's best amenities.

405 Birch Lane, Cutchogue

$1,599,000

3 Beds ⋅ 3 Baths ⋅ 1046222 MLS

790 Vanston Road is a meticulously maintained, spacious 1.5 story modified Cape set on a beautifully landscaped 0.65-acre lot in prestigious Nassau Point. This 3-bedroom, 3-bath home features a desirable first-floor primary suite, an open kitchen flowing seamlessly into the family room with a striking fireplace, creating the perfect setting for effortless entertaining. Separate living room, formal dining room, and bonus rooms galore provide flexibility for a home office, gym, or hobbies. Enjoy year-round living from the covered porch with radiant heat, host gatherings on the expansive patio, and take advantage of the generous yard, which offers plenty of room for a pool. Additional highlights include a 2-car garage, a partial house propane generator, and a full basement offering storage and future possibilities. New high-efficiency Reverse Osmosis (RO) water purification system and softener. 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 private bay beaches and rights-of-way providing water access to residents throughout the peninsula, along with the opportunity to join the voluntary community association.

790 Vanston Road, Cutchogue

$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

$1,549,000

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 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

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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.