Port Jefferson Homes with Pool

Welcome to the charming village of Port Jefferson, nestled in the picturesque Suffolk County of New York. This vibrant community is not only known for its stunning waterfront views and rich history but also boasts an exceptional school district that prioritizes academic excellence and holistic development. The Port Jefferson School District is renowned for its commitment to providing a well-rounded education, offering a variety of programs that cater to diverse learning styles. With dedicated teachers and a supportive environment, students thrive here, making it a sought-after area for families looking to settle down.

In addition to its educational offerings, Port Jefferson is a haven for those who appreciate the finer things in life, including homes with luxurious amenities. Imagine coming home to a beautiful property complete with your very own swimming pool—perfect for relaxing on warm summer days or hosting unforgettable gatherings with friends and family. The real estate market in Port Jefferson features a range of stunning homes, many of which include pools that enhance the outdoor living experience.

Living in Port Jefferson means enjoying a tight-knit community atmosphere while being surrounded by scenic beauty and top-notch schools. Whether you’re looking for a quaint cottage or a sprawling estate, you’ll find a variety of options that cater to your lifestyle and preferences. Embrace the opportunity to live in a place where education and leisure harmoniously coexist—welcome to your new home in Port Jefferson!

Newest Port Jefferson Homes with Pool

$699,999

3 Beds ⋅ 3 Baths ⋅ 1024284 MLS

Charming Cape in the Heart of Port Jefferson Village Filled with timeless charm and character, this beautifully maintained Cape offers the perfect blend of classic style and comfortable living. The spacious eat in kitchen offers abundant cabinetry and storage, along with a charming Dutch door providing easy access to the outside. Formal dining room opens to the den with gas fireplace and living room with a wood burning fireplace, all made for a warm and cozy home. The first floor includes a dedicated laundry space, powder room and a spacious primary bedroom suite with a large private bath, oversized tub, and separate shower. Upstairs offers two additional bedrooms and a full bath, providing plenty of space for family and guests. The charming enclosed porch is highlighted by a custom built brick indoor grill with propane hookup and a professionally vented hood, Separate heat zone offering a one of a kind setting for gatherings in every season. Step outside to your own private backyard retreat with a beautiful in ground pool, outdoor shower, and a Spacious Pool House complete with a spiral staircase leading to a versatile loft, perfect for a home office, studio, recreation room, or guest space. Additional features include a full basement with an outside entrance, two separate driveways providing ample parking, and exceptional outdoor living spaces. Ideally located in the sought after Village of Port Jefferson, this home is just minutes from the waterfront, restaurants, boutique shopping, parks, beaches, marinas, and year round community events. Convenient to Stony Brook University Hospital, Mather Hospital, the Long Island Rail Road, major roadways, and all the amenities that make Port Jefferson Village one of Long Island's most desirable places to call home. A rare opportunity to own a home filled with warmth, character, and endless possibilities in an exceptional location.

199 N Country Road, Port Jefferson

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 1018245 MLS

Welcome to 406 Brook Road, a gorgeous, turn-key colonial nestled in the heart of Port Jefferson village. Perfectly positioned to capture stunning winter water views, this meticulously maintained residence offers the ideal blend of timeless elegance and modern comfort. Step inside to discover an inviting entryway, leading to your open concept living space with gleaming hardwood floors, coffered ceilings, and thoughtfully designed spaces perfect for both everyday living, and entertaining. The gourmet kitchen is the heart of the home, and features leathered Taj Mahal countertops, Blue Star and Wolf appliances, and a lovely open layout allowing you to entertain your guests while you host. As you step upstairs, you’ll find generously sized bedrooms, including a luxurious owners suite designed as a private retreat, with a large en-suite bath, and walk-in closet. The large windows in the home, frame picturesque seasonal water views while filling the home with abundant natural light. The real show-stopper is the resort backyard, with a large in ground pool, outdoor kitchen, putting green, pergola, and much more. You don’t want to miss this show-stopper, just minutes away from all that exciting Port Jefferson Village has to offer.

406 Brook Road, Port Jefferson

$849,000

3 Beds ⋅ 4 Baths ⋅ 1015514 MLS

Come see this Move in Ready Colonial and call it your home! Freshly painted, Newly renovated bathrooms on the 2nd and 1st floor. Hardwood floors, abundant natural lighting throughout, Electric Appliances, Washer and Dryer room in basement. Big fenced in back yard with plenty of room for Entertainment! In ground swimming pool, deck, pavers around the pool in the back yard make it easy and fun to have a family BBQ or party! Wonderful area in the Village of Port Jeff! Minutes to St. Charles Hospital and Mather Hospital, Beautiful north shore beaches, Port Jeff Ferry, Restaurants and Entertainment!!! Don't Miss your Chance! Won't Last!

67 Soundview Drive, Port Jefferson

$1,599,000

5 Beds ⋅ 4 Baths ⋅ 1014504 MLS

Experience the essence of a Hampton-Style Classic Contemporary offering spectacular water views and an extraordinary outdoor lifestyle. This exceptional property features a beautifully designed backyard with expansive bluestone patio, spa, inground gunite heated pool, perfect for entertaining or peaceful relaxation. Enjoy a true country club lifestyle just minutes from private resident-only beaches, kayaking, sailing, harbor-front park, charming cafes, live theater, LIRR, Ferry service and nearby hospitals and university. A rare opportunity to embrace resort-like amenities and the best of the North Shore's coastal lifestyle. All in the renowned Port Jefferson School District! Property Details: - History: Meticulously maintained by the original owners since 1985. - Exterior: Situated on .53 acres featuring four multi-level mahogany decks, landscape lighting, Andersen windows, and fire/burglar alarms. - Recent Upgrades: Roof is under 15 years old; includes a new boiler and a new central air conditioning system. - Pool & Spa: Equipped with separate hot water heaters, filtration systems, and propane heaters. Recent updates include new tiles, marble dusting, and new jets, with a backwash system into a dry well. - Backup Power: Generac 22K propane generator with transfer switch. Interior Features: - Main Level: Open floor plan with cathedral ceilings and five skylights. Includes an entrance foyer, formal dining room, and an expansive living room. The primary bedroom features cathedral ceilings, built-in closets, and a full marble en-suite bath with a massaging jet bathtub. The chef’s Pedini-designed kitchen includes an island and Sub-Zero, Miele, Bosch, and GE Monogram appliances. This level also includes a washer/dryer closet, two additional bedrooms with cathedral ceilings, and a second full bathroom. - Lower Level: Large family room with Brazilian cherry floors, an additional large bedroom with an en-suite bathroom, a fifth bedroom, a play area, recessed lighting, and ample storage. Exterior Features: - Gardens: Multi-level gardens - Views: LI Sound, Mount Sinai Harbor, and Cedar Beach - Patio: Bluestone patio

32 Contessa Court, Port Jefferson

$1,799,999

5 Beds ⋅ 5 Baths ⋅ 1012794 MLS

Set on 1.5 acres overlooking a pristine golf course, 83 Cliff Road in Port Jefferson delivers the ultimate private resort lifestyle. This exceptional 5-bedroom, 5-bath residence is surrounded by breathtaking grounds featuring a pool, sports court, and dedicated pickleball area-designed for both elevated entertaining and everyday escape. Whether you're hosting unforgettable gatherings or enjoying quiet moments with sweeping views, this property offers a rare blend of space, privacy, and recreation-all in one extraordinary setting. This isn't just a home-it's your own personal retreat. Don't miss the opportunity to experience this one-of-kind property.

83 Cliff Road, Port Jefferson

$3,199,000

5 Beds ⋅ 8 Baths ⋅ 1004985 MLS

Experience unparalleled luxury and architectural grandeur in this extraordinary 15,092-square-foot estate where exceptional craftsmanship and resort-style amenities converge. Privately set behind a gated entrance with a circular driveway, this magnificent residence situated on 1.8 acres offers 5 bedrooms, 8 bathrooms, a 4-car garage, and an impressive array of indoor and outdoor living spaces designed for both lavish entertaining and comfortable everyday living. A dramatic entry foyer makes a lasting impression with a sweeping bridal staircase, a striking double-sided fireplace, and a spectacular illuminated stained-glass ceiling. Throughout the home, exquisite wainscoting, coffered ceilings, custom cornice moldings, and seven fireplaces showcase the meticulous attention to detail and superior quality of construction. The expansive main level features 13 beautifully appointed rooms, including elegant formal living and dining rooms, a richly appointed library, a spacious den, and two generously sized bedrooms. Every bedroom in the home enjoys the privacy and convenience of its own en-suite bath. The gourmet chef's kitchen is outfitted with premium Bosch, Wolf, and Sub-Zero appliances, offering the perfect setting for culinary excellence and entertaining. The luxurious primary suite serves as a private sanctuary, featuring a gracious sitting area, an expansive dressing room, and a spa-inspired en-suite bath complete with a soaking tub, oversized walk-in shower, dual vanities, and private balcony. A unique spiral staircase provides direct access from the suite to the indoor pool and sunroom, creating an unparalleled retreat experience. One of the home's most remarkable features is the enclosed sunroom, which houses a heated indoor in-ground pool and serves as a year-round resort oasis. This spectacular space also includes a fireplace, full bath, and built-in BBQ area, seamlessly blending relaxation and entertainment. An elevator services all four levels of the residence, providing effortless access throughout. The fully finished lower level offers an exceptional collection of amenities, including a media room, full kitchen, climate-controlled wine room, office, den, billiards room, and extensive recreation and gathering spaces. The outdoor grounds are equally impressive, highlighted by a heated saltwater in-ground pool surrounded by an expansive paver patio. A beautifully designed cabana features an outdoor kitchen, BBQ, and fireplace, creating the ultimate setting for outdoor entertaining and relaxation. Completing this extraordinary estate is a stately slate roof, further emphasizing the home's enduring quality and elegance. A rare offering of remarkable scale and distinction, this one-of-a-kind estate delivers an unmatched lifestyle of luxury, privacy, and resort-inspired living.

98 Cliff Road, Port Jefferson

$1,388,000

5 Beds ⋅ 5 Baths ⋅ 1009076 MLS

Inc Village--Drive through "The Gates to Belle Terre" onto Cliff road to a dead-end street near the water and discover this custom home in a Beach and Country Club community. The 1.61 acre wooded lot offers privacy with oval driveway and brick walkway to front door. Custom built by "Clarendon", this 4,252 sq ft home features open spaces and lots of light for today's living and entertaining with its huge deck, in-ground pool, 5 bedrooms, 4.5 baths , plus oversize primary with renovated bath and additional room for visiting parents and /or guests on main floor. The Village of Belle Terre has been designated as a bird sanctuary, has a private beach for residents, a park with children's playground, a pickle ball court, a summer program for children, and residents are also welcome at the Port Jefferson Country Club for golf membership. Belle Terre is located adjacent to quaint Port Jefferson Village with restaurants, shops, Library, Ferry to Bridgeport, deep water mooring for boats and 2 major hospitals. Belle Terre truly is "a beautiful place to live!"

6 Cliffside Drive, Port Jefferson

$999,000

4 Beds ⋅ 3 Baths ⋅ 962515 MLS

PRICE REDUCED!!! SELLERS ARE MOTIVATED! Move-in ready, this Harbor Hills post modern home offers a blend of sophisticated updates and timeless charm. The home has been fully renovated to meet the expectations of modern living. Boasting 4 bedrooms and 3 full baths, the bright, open-concept main floor is filled with natural light throughout, across its contemporary design. The sleek, updated kitchen is a chef’s dream, featuring modern cabinetry, a dedicated wine storage area, and a stylish breakfast bar—perfect for both entertaining and everyday living. On the upper level, the expansive primary suite is a true retreat at over 600 square feet, complete with a double doors, vaulted ceiling, cozy sitting area, custom walk-in closets, and a spa-like ensuite bathroom. You will also find two additional bedrooms and an updated full bath on this level. The lower level offers exceptional flexibility, providing endless possibilities, whether you envision it as a home office, guest quarters, or an inviting family room, and it even includes a full bath and private outside entrance for added convenience. Downstairs, the basement level provides entertaining space with a media room, as well as a storage room with laundry. Set on over half an acre of exquisitely landscaped grounds, the property is a private oasis, complete with a semi in-ground heated pool—ready for this summer's enjoyment. What truly sets this home apart is its location and lifestyle access: Its prime location, within the desirable Port Jefferson School District is near the LIRR, and just a short walk to the beach, golf course, hospitals, and Port Jefferson Village, where you will find the local charm and character of the live theater, parks, shops and restaurants, the convenience of the ferry to New England and even enjoy the marina with waterfront dining and beautiful sunsets over the LI Sound. Residents of the Incorporated Village of Port Jefferson have access to the sought-after north shore lifestyle, with resident-only access to multiple beaches on the Long Island Sound. Port Jefferson is a boater's dream, with several private and public marinas just minutes from Harbor Hills, and easy access to Port Jefferson Harbor offering fishing and water sports. For those considering a move away from the pace of city living, this home offers the opportunity to embrace a more relaxed, coastal lifestyle—without compromising on convenience, connectivity, or quality of life. You'll want to embrace the lifestyle that this North Shore location offers! PLEASE NOTE: With a tax grievance already in progress, the next owner is well-positioned to realize potential annual savings of approximately $2,000–$3,000 for the 2027 tax year. Tax grievance letter attached.

87 Soundview Drive, Port Jefferson

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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.