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$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 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
$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
$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
$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
$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
$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
$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
$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
$1,095,000
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
$1,250,000
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
$1,565,000
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
$8,250,000
1003778 MLS
Rarely does an opportunity of this magnitude surface on the North Fork - 44 contiguous acres of pristine, development-rights-intact land in the heart of Cutchogue, steps from the coveted Nassau Point Causeway Beach on Little Peconic Bay. This assemblage encompasses buildable terrain with sweeping sky and farmland vistas, coming to market at a pivotal moment in the North Fork's transformation into one of the East End's most sought-after locales. Full flexibility for a conservation subdivision, private estate, or boutique residential enclave, this is an end user, builder, or visionary's moment. The North Fork land market is moving - and properties of this scale, integrity, and proximity to the water do not wait.

3123 & 3595 Skunk Lane, Cutchogue
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 1001609 MLS
Welcome to Nassau Point, an iconic community in the heart of the North Fork. This serene waterfront home features a private dock and an exquisite pool, situated on Broadwater's Cove with direct access to Peconic Bay. Homeowners in this community enjoy private access to the sandy causeway beach and the point sandbar. Upon entry, you are welcomed by a spacious foyer that leads you either to the kitchen and entertaining space or down the hallway that opens to the bedrooms. This waterfront residence boasts four bedrooms, including a spacious primary suite with its own access to the waterside deck. The junior bedroom also has deck access and shares a bathroom with the third bedroom, which is located in a separate wing. The fourth bedroom, offering water views, can easily be converted into a home office or bonus space. The generously sized enclosed sunroom faces the cove, capturing stunning views and providing access to the wraparound deck. The renovated kitchen is well-appointed with a coastal palette, and the dining area features built-in window seating. The living room, equipped with a wood-burning fireplace, is designed for entertaining, boasting high ceilings and views that create a resort-like atmosphere. Outdoors, you'll find a beautiful new pool surrounded by terraced landscaping and a lounge patio, offering ample space for relaxation and entertainment. The home is also equipped with a generator and features a single detached garage. Conveniently located near all that the North Fork has to offer—wineries, beaches, shopping, and farm stands—this property offers privacy and exclusivity for the discerning buyer.

580 Broadwaters Road, Cutchogue
$2,800,000
4 Beds ⋅ 5 Baths ⋅ 998965 MLS
Sleek and thoughtfully executed, this contemporary build, designed by North Fork Modern Home, pairs a strong architectural point of view with a highly functional layout. High ceilings, polished concrete floors, and an expansive chef’s kitchen define the interior, while large openings draw in natural light and frame views of the beautifully composed backyard. The streamlined design is anchored by an open floor plan that connects the primary living, dining, and kitchen spaces, creating an easy flow for both everyday living and entertaining. A separate den and second-floor loft provide welcome separation for work, media, or quiet retreat when needed. Four ensuite bedrooms offer comfort and privacy for both residents and guests. Set on a shy acre with a sandy bay beach at the end of the street, the outdoor spaces are equally compelling, featuring a heated saltwater pool, expansive Ipe decking, and a covered dining area. Three of the four ensuite bedrooms offer direct access to the wraparound porch, which connects seamlessly to the home’s primary outdoor living spaces. The quality of materials and construction is evident throughout, reinforcing both form and function. Continuous poured concrete floors run throughout the home, creating a seamless, uninterrupted finish from room to room with no saddles or transitions. A two-car garage and substantial basement provide additional utility, storage, and flexibility. Located in the heart of Cutchogue, many of the North Fork’s best beaches, restaurants, wineries, and farm stands are just minutes away.

1895 Pequash Avenue, Cutchogue
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 997843 MLS
A bright and thoughtfully designed farmhouse in the heart of Cutchogue. Reimagined in 2017, the home underwent a comprehensive renovation that carefully blended its original charm with the modern conveniences of everyday living. Set on a beautifully landscaped and private shy half-acre, the property offers ample room for a pool and additional outdoor amenities. The renovation resulted in a substantially rebuilt and expanded residence featuring four bedrooms, 2.5 baths, and a flexible floor plan well-suited for both entertaining and relaxed year-round living. A generous wraparound front porch sets the tone for seamless indoor/outdoor living, while one of the North Fork’s most beloved bay beaches is located just a minute down the road. A rare opportunity to own a thoughtfully updated North Fork escape in an exceptional Cutchogue setting.

1270 Skunk Lane, Cutchogue
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 993662 MLS
Be in for summer, a very large home with over 2,200 square feet and 4 oversized bedrooms, this property already has a heated saltwater pool permit and all new furniture. Designer-owned and just received a brand new renovation, new electrical, new air conditioning, natural gas connected, this exceptional North Fork retreat seamlessly blends modern sophistication with timeless coastal charm. Perfectly positioned across from pristine protected land and a scenic golf course, the home offers tranquility, privacy, and effortless access to the very best of Cutchogue living. If you love golf, you are steps to Cedars Golf Club and can play every day. Ideally located just moments from the charming Cutchogue center, enjoy a 2 minute walk to town, local shops, restaurants, North Fork Country Club, and the Hampton Jitney with direct service to Manhattan. Spend your days biking to nearby New Suffolk, renowned North Fork beaches, acclaimed vineyards, Wickham's farm stand, and waterfront dining. Just 85 miles from Manhattan, and perfect location with no need for a car. Steps to the Historic Cutchogue Village Green and Peconic Community School. Bathed in natural light, the thoughtfully designed interior features new hardwood floors throughout and an open, airy floor plan ideal for both relaxed living and elegant entertaining. The spacious first-floor primary suite is a true sanctuary, complete with a spa-inspired en-suite bath featuring a brand new soaking tub and refined designer finishes. A second guest bedroom on the main level offers flexibility for visitors or home office use. The home contains all brand new solid wood doors, hardware, recessed lighting and fixtures. At the heart of the home is a stunning brand new chef’s kitchen appointed with premium stainless steel appliances, dishwasher drawers, deep porcelain sink, and an inviting eat-in dining area highlighted by a Serena & Lily chandelier. The oversized living room with a sleek modern electric fireplace flows effortlessly into the separate dining area, creating the perfect setting for gatherings year-round. Upstairs, two generously sized bedrooms with a brand new beautifully appointed en-suite bath, offering comfort and privacy for guests. Outside, professionally landscaped grounds bloom with lush flowers and mature plantings, while the covered porch provides the perfect backdrop for alfresco dining and summer evenings. The expansive backyard features room for a 16x32 heated saltwater pool, creating a true resort-like atmosphere. The Pool permit is already secured and can be installed for this summer. Additional highlights include a very large and dry basement that can be finished, oversized two-car garage, and new furnishings available separately for a completely turnkey experience. Whether seeking an upscale summer escape, luxurious year-round residence, or exceptional investment opportunity, this move-in-ready home embodies the very best of North Fork living. New owner can immediately rent for the summer if desired.

440 Cases Lane, Cutchogue
$2,600,000
994920 MLS
Cutchogue—17.5 acres of level, fertile land. Development rights intact. Agricultural potential and/or subdivision and other options. This property includes an 1800s farmhouse, a 2600 sf barn with horse stalls, water and electric, outbuildings, and 4.5 acres of vines planted in Merlot, Sauvignon Blanc and Riesling varitals. The manageable land size is suitable for an eco-friendly, entry level enterprise or additional acreage for an established owner looking to increase crop production. Suitable for but not limited to grape production. Opportunity abounds in this 17.5 acre, development rights intact property in Cutchogue, the sunniest place in New York State. REALLY! Central, accessible North Fork location. Bring your concept to life here.

35950 Main Road, Cutchogue
$2,300,000
5 Beds ⋅ 5 Baths ⋅ 994272 MLS
Clad in cedar and built with meticulous attention to craftsmanship, this brand-new custom home sits proudly on a generous 0.59 acres, just moments from downtown Cutchogue. Timeless in design, the heart of the home is a striking open-concept kitchen with beautiful cabinetry, an oversized island, and seamless flow into a light-filled dining area overlooking the expansive backyard. The living room, anchored by a fireplace, features custom millwork and opens to a covered bluestone porch, creating an easy connection between indoor and outdoor living. First-floor highlights include a large primary suite with an ensuite bath and large closet, an additional ensuite guest bedroom and a laundry room. Upstairs, a spacious second primary ensuite and two additional ensuite guest bedrooms sit across from a very large recreation room, perfect for movies, gym or office. A two-car garage with heated floors adds both function and flexibility, while the full-height basement with egress offers future expansion potential. Located in the heart of the North Fork, just minutes from golf, farm stands, wineries, restaurants, schools, and many of the region’s most sought-after amenities.

26745 Main Road, Cutchogue
$2,600,000
3 Beds ⋅ 2 Baths ⋅ 994280 MLS
Cutchogue Farmstead. Ideal North Fork location. This property includes the home, a 2600 sf barn with horse stalls, water and electric, outbuildings, and 4.5 acres of vines planted in Merlot, Sauvignon Blanc and Riesling varietals. This 1800's restored farmhouse is set on 17.5 acres of level, fertile land. Development rights are intact offering not only agricultural potential but also subdivision and other options. The farmstead's manageable land size is suitable for an eco-friendly, entry level enterprise and also offers additional acreage to an established owner looking to increase crop production. The 3BR, 2 BA farmhouse has a lovely, covered porch with a Western exposure, great for afternoon get-togethers. A patio with a pergola overlooks the planted vines. Opportunity abounds in this 17.5-acre, development rights intact property in Cutchogue, the sunniest place in New York State. REALLY! Central, accessible North Fork location. Bring your concept to life here.

35950 Main Road, Cutchogue
$2,500,000
993359 MLS
Set along the iconic agricultural stretch of the Main Road in the heart of Cutchogue, this expansive 37+ acre Agricultural Conservation (AC) property offers a rare and compelling blend of beauty, scale, and opportunity. The land unfolds in a striking patchwork of cultivated rows and open fields-an inspiring canvas for anyone looking to grow, expand, or create something truly special. Approximately 20 acres are currently under vine, presenting immediate income-producing potential, with much of the existing fruit ready to be sold. The remaining 17 acres of open agricultural land invite your vision-whether that’s additional plantings, specialty crops, equestrian use, cattle, or a boutique farm operation. Varietals include Pinot Noir (1 acre); Cabernet Franc (3 acres); Malbec 3 acres); Petit Verdot (2.2 acres); Merlot (3 acres); Chardonnay (2.5 acres); Riesling (1.4 acres); Gerwurtztraminer (2.6 acres). The property benefits from exceptional frontage, offering both visibility and accessibility. Supporting the agricultural infrastructure is a substantial 2,700 sq. ft. cedar barn with electric, ideal for storage, operations, or future adaptation. Three wells service the property, including one electric well for the barn and two diesel wells strategically located in the fields, ensuring functionality and efficiency across the acreage. Whether you are an established farmer, an investor, or someone ready to turn a dream of land stewardship into reality, this property offers a unique opportunity to step into a productive, picturesque setting with room to grow.

37025 Main Road, Cutchogue
$5,999,000
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
$2,995,000
4 Beds ⋅ 5 Baths ⋅ 984475 MLS
CHIC, SLEEK, AND COMPLETELY UNIQUE - This industrial chic modern hits every box. Open concept living, radiant heated concrete floors throughout. A floating fireplace and walls of glass bringing the outdoors straight into the everyday. The living space spills out to the private heated Gunite saltwater pool, expansive patio and outdoor shower - creating an indoor-outdoor flow that feels polished, relaxed, and spa-like. A covered patio provides space for al-fresco dining. With 4 bedrooms, 4.5 baths, a dedicated laundry room, and parking for 5 cars between the garage and carport, this property delivers an elevated design, completely unique to the North Fork on every level. Stroll to restaurants, farm stands, and into town. Easy in and out to NYC and surrounded by beaches and renowned vineyards!

2050 Depot Lane, Cutchogue
$3,200,000
6 Beds ⋅ 7 Baths ⋅ 979297 MLS
Your North Fork Escape | Modern Coastal Living in Nassau Point 1355 Little Peconic Bay Road is a newly constructed 4,600 + 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
$682,000
3 Beds ⋅ 1 Baths ⋅ 972514 MLS
Opportunity Awaits In The Heart of Cutchogue! This 3-bedroom, 1-Bath Home Sits On A Beautiful 0.66-Acre Flat Property, Offering Endless Potential For Renovation, Expansion, Or Customization. This Home Has Solid Structure And Great Bones, Making It The Perfect Canvas For Buyers Looking To Create Their Dream North Fork Sanctuary. The Large, Level Yard Provides Plenty Of Space For Gardens, Outdoor Entertaining, Or Creating Your Own Private North Fork Retreat. With Its Desirable Location Near Farms, Wineries, And Beaches, This Property Is Perfect For Buyers Looking To Invest In The North Fork Lifestyle. Offered As An "As Is" Sale. Newer Windows/Roof/Siding (2021), 100-Amp Electric Service, Poured Concrete Cement Basement. Buyer Pays Peconic Tax. Motivated Seller Willing To Hear All Offers!

16400 County Road 48, 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
$5,925,000
4 Beds ⋅ 5 Baths ⋅ 972084 MLS
Cutchogue Showstopper. Perched atop a 55-foot bluff overlooking the Long Island Sound, this extraordinary Barnes Coy designed waterfront home offers rare architectural pedigree and an unrepeatable setting. Designed by Barnes Coy Architects, the award-winning firm known for some of the East End’s most distinctive modern residences, this 4,200 SF jewel box estate is set within a private neighborhood with its own park and private stairs to the beach. Filled with natural light and premium finishes, the home features polished limestone floors with radiant heat, two primary ensuite bedrooms with ample closet space, smart home technology controlling lights, blinds, temperature, and front gate; solar panels for energy efficiency, and a full-house generator. The lower level with full bath offers flexible space for a media room, gym, office, or guest overflow. An attached two-car garage is also included. Outside, a heated saltwater gunite pool, hot tub, 1000 sf rooftop deck, firepit, and back lawn create an exceptional waterfront setting for entertaining or quiet enjoyment. Enjoy breathtaking sunsets from the rooftop deck or pool, practice yoga with wide water views, or watch seals gather on the rocks below. An outdoor shower with interior and exterior access adds ease after the beach or pool, and there is room to create an outdoor dining and kitchen area. A truly architecturally significant North Fork offering with exceptional water views, spectacular sunsets, privacy, and a setting that simply cannot be recreated.

445 Glen Court, 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

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