Cutchogue Real Estate

Welcome to Cutchogue, a hidden gem nestled in the heart of Long Island’s North Fork, New York. This charming hamlet, part of Suffolk County, is known for its picturesque landscapes, rich history, and vibrant community. As you wander through Cutchogue, you’ll be captivated by its serene ambiance, where lush vineyards and rolling farmlands create a stunning backdrop for everyday life.

Cutchogue boasts a unique blend of rustic charm and modern convenience. With a population that values a close-knit community, residents enjoy a peaceful lifestyle while being just a stone’s throw away from the bustling towns of Southold and Mattituck. The area is renowned for its wineries, offering wine enthusiasts a delightful array of tastings and tours, making it a perfect destination for a weekend getaway or a leisurely afternoon.

Outdoor lovers will find plenty to explore in Cutchogue, from scenic parks to beautiful beaches along the Peconic Bay. The nearby Cutchogue Harbor offers opportunities for boating, fishing, and kayaking, while the surrounding nature preserves provide the perfect setting for hiking and birdwatching.

Cutchogue is also steeped in history, with landmarks like the Cutchogue Village Green and the historic Cutchogue New Suffolk Free Library, which tell the story of this quaint community. With a strong sense of local pride, residents come together for seasonal events and farmers’ markets, celebrating the area’s agricultural roots.

Whether you're looking to settle down, invest in a vacation home, or simply explore, Cutchogue offers a delightful blend of tranquility and charm, making it an ideal place to call home.

Newest Listings in Cutchogue

$1,800,000

5 Beds ⋅ 3 Baths ⋅ 1053916 MLS

A Coastal Classic with Endless Possibilities -Set in one of Cutchogue’s most desirable locations, this spacious Coastal Dutch Colonial showcases the timeless character of its signature gambrel roof, complemented by modern updates and an exceptional North Fork lifestyle. Featuring five bedrooms and three bathrooms, this inviting residence offers generous space, versatility, and a rare opportunity to live and work on the same property. Fenced in yard with deck, and room for a large in ground swimming pool. Just a short walk to the beautiful sandy shoreline of Pequash Beach, enjoy the best of coastal living with bay beach swimming, kayaking, a playground, and a nearby marina with boat dockage. Whether spending summer days on the water or enjoying the peaceful surroundings of this sought-after beach community, the setting captures the very best of the North Fork. Adding extraordinary value and flexibility is a separate garage with car lift accompanied by a rare license to operate a New York State Auto Repair Shop, presenting a unique opportunity for an owner-operator to combine home and business in one location. Alternatively, this versatile structure offers exciting possibilities for a car collection, creative studio, gardening retreat, or potential future accessory cottage. Set on a generous, nearly one-acre property along a quiet street, this distinctive offering provides room to enjoy, expand, and envision the possibilities. Conveniently located near Cutchogue town, Wickham’s Farm Stand, Peconic Bay Vineyards, New Suffolk, celebrated local restaurants, and the North Fork’s renowned beaches, vineyards, and farm stands, this is a rare opportunity to own a property that combines classic coastal architecture, exceptional flexibility, and an enviable lifestyle.

270 Pequash Avenue, Cutchogue

$679,000

1059356 MLS

Discover the possibilities of this residential building lot in the heart of Cutchogue. Situated along bucolic Alvah’s Lane and surrounded by attractive neighboring homes, this property presents an exceptional opportunity to create your custom North Fork residence. With a naturally open central area, mature trees providing a sense of privacy, direct road frontage, and an existing well with an electric pump, the property offers an inviting setting for a thoughtfully designed home and outdoor living space. Enjoy the charm of North Fork living, with renowned vineyards, farm stands, beautiful beaches, restaurants, and picturesque villages just moments away. Whether you envision a year-round residence or a weekend retreat, this is your opportunity to bring your vision to life in one of the North Fork's most desirable communities. Bring your builder and your dreams!

3850 Alvahs Lane, Cutchogue

$3,200,000

6 Beds ⋅ 7 Baths ⋅ 1058733 MLS

Your North Fork Escape | Modern Coastal Living in Nassau Point 1355 Little Peconic Bay Road is a newly constructed 4,760 square foot residence in the coveted Nassau Point area of Cutchogue, offering refined North Fork living moments from Fisherman Beach and the shoreline of Little Peconic Bay. Set on over an acre, this modern coastal home combines scale, comfort, and high-end finishes in a prime Cutchogue location. This six-bedroom, six-and-a-half-bath home is designed for both scale and comfort. The main level centers on a dramatic double-height living room with approximately 18-foot ceilings and expansive windows that flood the space with natural light, creating an impressive yet welcoming setting for everyday living and entertaining. Adjacent is a chef's kitchen featuring custom walnut cabinetry, Taj Mahal quartzite countertops, and a walk-in pantry, combining elevated design with practical functionality. The bedroom layout is thoughtfully distributed across the home, providing flexibility for guests, multigenerational living, or dedicated office and hobby spaces. Each full bathroom is well proportioned for privacy and convenience, while a centrally located powder room serves the main living areas. Circulation and storage have been carefully considered, allowing for an easy flow between public and private spaces. A fully finished lower level adds approximately 2,575 ; square feet of additional living area, offering exceptional versatility. This level can accommodate extra bedrooms, a gym, media room, game room, or wellness and recreation spaces, expanding the home's potential for a variety of lifestyles. The outdoor environment is equally appealing. An 18 x 36 heated saltwater pool with an outdoor shower anchors the rear grounds, creating a focal point for summer living, relaxation, and entertaining. The property's generous lot size allows for both open lawn and more intimate areas for quiet retreat. Additional features include an oversized two-car garage with sufficient height to accommodate a car lift, offering flexibility for car enthusiasts or additional storage. Set within Nassau Point, this home is surrounded by some of the North Fork's most notable coastal scenery, with convenient access to bay beaches, boating, local vineyards, and farmstands. The location offers a balance of privacy, space, and proximity to the water, enhancing the property's appeal as a primary residence, weekend escape, or seasonal home. 1355 Little Peconic Bay Road represents a substantial, well-executed new construction opportunity in one of Cutchogue's most sought-after enclaves, combining modern amenities, thoughtful design, and a premier coastal setting on the North Fork.

1355 Little Peconic Bay Road, Cutchogue

$1,349,000

1057972 MLS

Great opportunity located in Cutchogue - Limited Business Zone. Town Code attached. Currently used as an outdoor nursery business (retail & wholesale) with other storage and sales display. 220 electric on site, 10 parking stalls. Property consists of 1.454 acres. Current use is for nursery purposes only. Rare opportunity to purchase such a large piece of property in Cutchogue's Limited Business Zone. Bring your vision & dream!

36660 Main Road, 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

$2,149,000

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

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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.