Mattituck-Cutchogue Homes with Pool

Welcome to the Mattituck-Cutchogue school district, a gem nestled in the heart of Suffolk County, New York. Known for its commitment to educational excellence, this district serves a vibrant community that values both academic achievement and personal growth. With a strong emphasis on holistic education, Mattituck-Cutchogue offers a diverse range of programs designed to cater to the unique needs of its students, from innovative STEM initiatives to arts and athletics. Parents can rest easy knowing that their children are learning in a supportive environment that fosters creativity, critical thinking, and character development.

Beyond the classroom, the picturesque North Fork of Long Island provides an idyllic backdrop for family life. The area is celebrated for its breathtaking landscapes, charming vineyards, and stunning waterfronts, making it a perfect place to call home. For those seeking the ultimate in relaxation and leisure, many homes in this region feature inviting pools, transforming your backyard into a private oasis. Whether you're hosting summer barbecues or enjoying a quiet evening under the stars, a home with a pool adds an extra layer of enjoyment to the idyllic lifestyle offered by Mattituck-Cutchogue.

With its excellent schools, community spirit, and beautiful homes with pools, the Mattituck-Cutchogue area is not just a place to live—it's a place to thrive. Explore the opportunities that await you in this enchanting part of Suffolk County, where education and lifestyle harmoniously blend to create a vibrant community perfect for families and individuals alike.

Newest Mattituck-Cutchogue Homes with Pool

$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

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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.