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$1,425,000
4 Beds ⋅ 4 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. Set of .92 acres offering effortless indoor-outdoor living. The open concept kitchen offers both Silestone and Butcher block countertops with modern floating shelves and ample cabinetry. 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 creates the perfect spacer for relaxation and entertaining. The family room has a wood burning fireplace to cozy up to on those cold winter days. Two additional upper level bedrooms and full bath 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. The out-door lighting provides a tranquil atmosphere allowing for to entertaining into the evening,, all designed to provide a peaceful setting right in the comfort of your home. A rare opportunity to own your own slice of paradise, close to beaches, restaurants and wineries. Priced to sell House is being sold as is. .

1850 Highland Road, Cutchogue
$2,745,000
4 Beds ⋅ 4 Baths ⋅ 1029802 MLS
Situated on over two acres within an exclusive cul-de-sac, this newly constructed residence built by renowned builder Southampton Building Company Corp., is now on the market! The home is just moments from Breakwater Beach, the Long Island Sound and Mattituck Inlet, offering convenient access to beaches, boating and the best of North Fork living. The Developer features four bedrooms and four full bathrooms, including two luxurious primary suites, one conveniently located on the first floor and another on the second. The chef’s kitchen is appointed with top-tier appliances, including a 48-inch dual-fuel double-oven range, professional-grade vent hood and wine refrigerator, creating a space that is as functional as it is beautiful. A sprawling lower level with 10-foot ceilings, three egress windows and a private exterior entrance offers exceptional flexibility for recreation, wellness, or future customization. A fully customizable and expandable smart-home system, radiant-heated flooring throughout, custom-designed closets and premium finishes throughout reflect an exceptional level of quality and craftsmanship. Builders 5000 sq.ft. expansive patios extend the living spaces outdoors, creating an inviting setting for entertaining and relaxation. The private backyard is highlighted by a spectacular 20-by-60-ft heated saltwater pool with an automatic cover, along with a dedicated sport court designed for pickleball and basketball. Combining exceptional design, uncompromising quality, and an irreplaceable location, this is a rare opportunity to own a true legacy property in one of Mattituck’s most desirable enclaves. Home includes three levels of furnishings, full arborvitae privacy screening and an extensive new construction warranty package for the home and pool

2790 Stanley Road, Mattituck
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 1027823 MLS
Welcome home to this North Fork retreat! The perfect getaway for peace and relaxation. Tucked away on a charming lane, this beautifully maintained home and features a resort-style yard centered around an in-ground pool and patio, creating the ultimate setting for entertaining. Inside this renovated home, there is plenty of room for everyone and offers a seamless flow between indoor and outdoor living. Location is everything, and this property has it all. Take a short stroll to the beach for swimming, kayaking, paddle boarding. Boating and fishing enthusiasts will appreciate being just down the road from Strong’s Marina, offering easy access to the best boating on The Peconic Bay. Whether you’re searching for a full-time residence, weekend escape, or investment opportunity, this home has it all. Close to Love Lane, shopping, restaurants, wineries, transportation and all the best Mattituck has to offer.

475 Alois Lane, Mattituck
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 1027794 MLS
This impeccably maintained residence is perfectly positioned in the heart of Mattituck, just minutes from local beaches, Love Lane, New Suffolk, and downtown Cutchogue. Set on a beautifully landscaped acre, the property offers a large in-ground pool, mature gardens, and ample room to add additional amenities such as a tennis court or accessory structure. Inside, a bright, open-concept floor plan lends itself to both everyday living and entertaining, featuring a large chefs kitchen, dining room and living room. The oversized primary suite serves as a private retreat, complete with a spacious en-suite bath and generous walk-in closets. Two additional guest bedrooms and a large home office provide flexibility for visitors, or remote work. A large laundry room, basement and detached garage provide for additional utility. Sit on your back patio overlooking the pool to take in spectacular East End sunsets. Thoughtfully maintained and ideally located, this is a home that pairs comfort, convenience, and future potential in one of the North Fork's most desirable communities.

1430 Marratooka Road, Mattituck
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 1025976 MLS
Newly renovated and masterfully designed, this exceptional home features three spacious ensuite bedrooms, plus an additional bedroom on the walk-out lower level. The open-concept floor plan with soaring ceilings, is highlighted by dramatic floor-to-ceiling windows and doors that frame breathtaking panoramic views of the surrounding landscape while filling the home with natural light. This is an exclusive opportunity to own a turn-key modern 3200 sq ft home on three levels with a brand new sparkling pool, and cascading landscapes and stone walkways and patios. The interior flows seamlessly onto the expansive hilltop deck, creating the perfect setting for comfortable outdoor living and effortless entertaining. Whether enjoying quiet mornings overlooking the scenery or hosting guests against a stunning natural backdrop, this home offers an exceptional blend of luxury, comfort, and style. This amazing home is conveniently located to Breakwater Beach with deeded Creek access. Enjoy the wonderful Northfork lifestyle. *Some photos are virtually staged. --

1380 Jackson Landing, Mattituck
$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
$998,000
5 Beds ⋅ 4 Baths ⋅ 1012027 MLS
Welcome to 1520 Meday Avenue, a rare mid-century modern ranch built in 1977 and ideally located in the heart of Mattituck on Long Island’s coveted North Fork. Offering 5 bedrooms and 4 full bathrooms, this expansive residence combines classic architectural character with exceptional scale, privacy, and resort-style outdoor living. Designed around a striking central courtyard, the home is oriented to maximize natural light and views from nearly every room, creating a seamless connection between indoor and outdoor spaces. At the heart of the property lies a private in-ground pool, beautifully positioned within the courtyard and surrounded by a putting green—transforming the entire center of the home into a one-of-a-kind private retreat. Inside, the home features a spacious living room with fireplace, an open-concept kitchen, and a large dining room that together create an easy, flowing layout ideal for entertaining and everyday living. All bedrooms are generously sized, offering comfort, flexibility, and privacy for family and guests alike. While the home is well maintained and structurally sound, it presents an excellent opportunity for thoughtful updating—allowing a new owner to enhance and personalize a truly special architectural canvas while immediately enjoying its exceptional layout and setting. Located just minutes from Mattituck’s vineyards, farm stands, beaches, marinas, boutique shopping, and acclaimed restaurants, this property captures the very best of North Fork living. Whether envisioned as a year-round residence or a seasonal retreat, 1520 Meday Avenue offers a rare combination of space, design, and lifestyle in one of the region’s most desirable communities. A distinctive courtyard ranch with resort-style amenities, this is an opportunity to create something truly extraordinary.

1520 Meday Avenue, Mattituck
$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
$6,450,000
6 Beds ⋅ 8 Baths ⋅ 1021701 MLS
Introducing 1775 Point Pleasant, a newly constructed waterfront estate set on 1.8 acres with over 280 feet of pristine creek-frontage along iconic Mattituck Inlet. Thoughtfully designed and expertly crafted, this exceptional shingle sided Post-Modern style residence seamlessly blends timeless architecture with modern luxury. Spanning more than 7,000 square feet, the home showcases wide-plank hardwood flooring throughout, dual primary suites on both the first and second levels, a fully finished lower-level with private fitness studio, sauna, climate controlled wine storage, an unmatched custom lighting package, pre-wired recessed speaker system and expansive living spaces on all three levels designed for both everyday comfort and effortless entertaining. At the heart of the home is a chef's kitchen appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, multiple beverage stations and refined finishes throughout. Outdoors, resort-inspired amenities await, including a heated 22'x44' gunite pool surrounded by an expansive travertine terrace, fully equipped outdoor kitchen, a covered lounge with ceiling mounted heaters for those cooler nights and anchored by a third wood-burning fireplace, creating an ideal setting for waterfront entertaining. Finally, enjoy a manicured path of travertine stepping pads that lead to an oversized floating dock, equipped with water and electric, that can easily house a large boat with deep draft, perfectly capping off this incredible custom build opportunity. Offering an extraordinary combination of scale, privacy, craftsmanship, and lifestyle, 1775 Point Pleasant represents a rare opportunity to own a truly exceptional waterfront retreat on the North Fork.

1775 Point Pleasant Road, Mattituck
$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
$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
3 Beds ⋅ 2 Baths ⋅ 998812 MLS
Mattituck, North Fork: Where lifestyle, flexibility, and investment potential come together. Discover sunshine and serenity in this impeccably renovated retreat, ideally located in one of the North Fork's most sought-after settings. Completely renovated in 2024, this turnkey home offers not only exceptional comfort and style, but also a proven track record of strong summer rental income, making it an outstanding opportunity for personal use, income generation, or a seamless combination of both. Set on a spacious, level, and private one-acre property surrounded by tall evergreens, the home features a brand-new heated saltwater gunite pool (16x34) complete with an approximately 800 square foot thermal bluestone patio, creating a true resort-like experience right in your backyard. Inside, expansive open living spaces are filled with natural light, offering a bright and welcoming atmosphere throughout. The first-floor owner's suite is impressively sized and features a dedicated sitting area or office—perfect for remote work or a peaceful retreat. A beautifully appointed full bath featuring imported artisanal Spanish tile on the main level is thoughtfully positioned to serve both the suite and main living areas with ease, enhancing convenience for everyday living and entertaining alike. The open-concept kitchen with stainless steel appliances and dining area flow effortlessly to an outdoor deck overlooking the verdant property and swimming pool with terrace, while the spacious living room provides an inviting setting for relaxation in any season. Upstairs, two additional bedrooms and a full bath comfortably accommodate guests. Adding to the home's versatility is an oversized two-car garage, offering excellent potential for conversion into additional living space—ideal for a den, media room, or expanded entertaining area. A full unfinished basement with laundry and utilities provides abundant storage or future finishing possibilities, while a large unfinished bonus room above the garage presents yet another opportunity to customize and expand. Additional upgrades include a new dual-zone Bosch heat pump HVAC system w/ Ecobee thermostats, a whole-house water filtration system, Visual Comfort lighting, Shade Store window treatments, a new six-zone sprinkler system, and a new roof. Conveniently located near renowned North Fork vineyards, the charm of Love Lane, and both Long Island Sound and Peconic Bay beaches, this home delivers the ideal blend of location, lifestyle, and long-term value. Immaculate, adaptable, and income-producing—this is a rare chance to own a North Fork property that truly does it all.

820 Gabriella Court, Mattituck
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 986519 MLS
Masterfully built, blending timeless design with modern comforts and expert craftsmanship, creating an undeniable sense of harmony and place, on a lovely 1/2-acre level lot, just moments from Love Lane, Strong's Marina and Bailey Beach 3000 Grand Ave. is the perfect North Fork country house. Clad in classic cedar shingles and anchored by a welcoming front porch, this home immediately feels like the perfect North Fork retreat. Inside, uplifting natural light pours through expansive windows, illuminating an elegant foyer and dining room. The kitchen supports both everyday living and effortless entertaining, featuring Quartz countertops, stainless steel appliances, drawer microwave and a generous island. The first floor also includes a lovely private ensuite bedroom. On the second floor we find the primary suite, a serene sanctuary, featuring a spa inspired bath. Two additional guest bedrooms share this level. The exterior is designed for outdoor enjoyment featuring a heated saltwater pool with expansive paver patio. New construction with completion in Fall 2026

3000 Grand Avenue, Mattituck
$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
$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
$4,350,000
3 Beds ⋅ 2 Baths ⋅ 976938 MLS
MAGIC ON OREGON ROAD Romance, Elegance and Timeless beauty over 38 acres on bucolic Oregon Road, you couldn't ask for anything more! 36 acres of DRS land which includes 30 planted acres of grape vines, deer fencing and bird netting, irrigation in place for an additional 2-3 acres of planting and a potential wine tasting area. The updated vintage farmhouse rests on 2 acres of DRI land and features 3 bedrooms, 2 bathrooms, sun drenched open floor plan, eat-in-kitchen, dining area, sitting area with reading nook, living room with a fireplace. Step outside and enjoy lush landscape surrounding the pool, outdoor shower and vineyard views! Surrounded by award winning North Fork wineries, restaurants, farm stands, boating & great shopping.

2600 Oregon Road, Mattituck
$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
$3,750,000
3 Beds ⋅ 5 Baths ⋅ 963336 MLS
SOUND FRONT RETREAT - Designed in 1986 by architect Sanford Hanauer for his own residence and reimagined in 2011, this elegant homestead is modern luxury done the right way. Set high above the shoreline on 2.45 acres with 200 feet of direct beachfront, angled so the water is the constant-nearly every room, every day, every season. Floor-to-ceiling glass pulls in the light, while bluestone accents, wide ash plank floors, and three fireplaces keep it warm and grounded. The Eggersmann kitchen with a butler's pantry is as timeless as it is functional, ready for quiet mornings, long lunches, and the kind of dinners that start at golden hour and somehow become tradition. Outside, the 50-foot pool is set discreetly into the bluff-private, protected, yet open water views. Two additional bedrooms are positioned to work like a separate guest cottage-ideal for extended stays or flexible space for work. A loft, multiple decks, and sun-soaked patios make indoor-outdoor living feel natural-because here, the view is the backdrop to everything. The white-stained cedar exterior blends seamlessly with the landscape. From white Italian marble baths to that last ray of sunset on the patio as the sky turns soft over the Sound, this is a home designed to inspire and never lose power with a full house generator.

4105 Soundview Avenue, Mattituck
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 932413 MLS
17525 County Rd. 48 (aka Middle Rd). Currently being used as a "tree farm", large farmhouse w/high ceilings, open living/dining area, craft room, den and office space. First floor full bath, full row of storage closets. Second floor offers large primary bedroom with high ceilings & 2 additional bedrooms, full bath. Inground pool, large patio area, huge accessory building with large overhead door, 2.06 acres (150 x 600) with partial irrigation zoned AC Agriculture Conservation (Residential). Endless possibilities with large outbuilding for the hobby enthusiast, country farmer or one looking for a serene lifestyle amongst the beautiful North Fork surroundings.

17525 County Road 48, Cutchogue
$4,995,000
6 Beds ⋅ 7 Baths ⋅ 894818 MLS
Brand new exquisite waterfront 6 bedroom, 7 bathroom home set on 1.33 acres along coveted Mattituck Inlet in the heart of the North Fork, this exceptional waterfront retreat spans approximately 5,920 square feet of refined living space, blending classic Hamptons-style cedar-shingle architecture with a sophisticated, contemporary interior. Designed for both elegance and everyday comfort, the home features an airy open-concept layout anchored by a dramatic great room with soaring ceilings, expansive Andersen 400 Series double-hung windows, and walls of glass framing panoramic water views. A Heat & Glo 36” propane fireplace with tranquil surround, LED lighting, fan blower, and multi-function remote adds warmth and ambiance. The chef’s kitchen is a true showpiece, appointed with full overlay cabinetry with glass-top cabinets extending to the ceiling, quartz countertops, and a premium appliance suite including a 48” Sub-Zero refrigerator, 48” Wolf gas range, 30” Wolf double wall oven, 24” Wolf microwave, and 24” Miele dishwasher—all stainless steel. The kitchen flows seamlessly into the dining area and outdoor entertaining spaces. The primary suite offers a spa-inspired retreat with radiant electric floor heating in the primary and junior primary baths, private terrace access, and serene water views. Wide-plank 7” plain-sawn white oak flooring runs throughout, enhancing the home’s warm yet modern aesthetic. Additional bedrooms are generously sized and thoughtfully designed for privacy and comfort. Outdoor living is exceptional, featuring a heated 20’ x 40’ gunite saltwater pool with jacuzzi, surrounded by imported Marmiro Stone (Afyon Cloud) patios, a mahogany primary deck, covered porch, and landscaped grounds serviced by a 10-zone Hunter irrigation system. The property includes metal and cedar fencing, a private dock, and direct waterfront access—ideal for boating and waterside living. Additional highlights include state-of-the-art, energy efficient, multi zone HVAC (every bedroom and common area has its own thermostat - the system has multiple fans for dedicated zones), central air, public water, septic system, a two-car garage, cedar shingle roof and siding with white double-dipped finish. Surrounded by vineyards, farm stands, and pristine North Fork beaches, this extraordinary waterfront estate delivers modern luxury, timeless craftsmanship, and the relaxed elegance of Long Island’s wine country—an unparalleled opportunity for refined coastal living.

2590 Cox Neck Road, Mattituck
$4,859,000
6 Beds ⋅ 9 Baths ⋅ 894800 MLS
Luxury New Construction at its finest! Located in coveted Nassau Point and situated on nearly two verdant acres, this stately 8,500+ sq. ft. home features three-levels of meticulously crafted living space. The impressive entry foyer immediately sets the tone for grandeur with front to back living room doors, tasteful herringbone oak floors, 10' ceilings, custom mill work and views beyond of the patio through a wall of glistering glass. The lavish designer kitchen showcases a 9' island, Sub-Zero & Wolf appliances, 2 Bosch dishwashers, 3 wine fridges, and a 7x14 cleverly hidden walk-in pantry. Adjacent to this open floor plan is the dining area and the great room with statement gas burning fireplace and floor to ceiling windows and doors accessing over 1,000 square feet of covered and uncovered stone patios. There are six ensuite bedrooms all with radiant heated bathrooms including 2 Primary suites. One is conveniently located in a separate wing on the first floor and the second is located upstairs - boasting a spa-like bathroom and a private 400 square ft. covered terrace. The sun-drenched lower level offers walk-out access to the rear property including an outdoor shower and 18x36 saltwater pool. There is also ample room for tennis courts. The lower level serves as a cabana area with a recreational room and beverage center, gym area, sauna and bonus rooms providing the ideal space for a home theater and wine cellar. Additional features include a whole house generator, a 30X60 stand up attic plus a 3 car garage. This is more than a home - it is a lifestyle. Enjoy multiple expansive sandy beaches just a stone's throw away and all the North Fork is so well known for - vineyards, world class dining, boating, farms and more.

3360 Wunneweta Road, Cutchogue

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