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$1,295,000
4 Beds ⋅ 3 Baths ⋅ 1032540 MLS
Perfectly positioned within the prestigious Incorporated village of Port Jefferson,56 Old Homestead Road presents an exceptional opportunity to own a private luxury home in one of Long Island's most coveted waterfront communities.Nestled on .93 acres of exquisitely manicured grounds, this 3000-square-foot multi-level contemporary ranch features 4 bedrooms, 3 full baths and an extraordinary blend of sophisticated living and resort-inspired amenities. Double entry doors into an impressive open-concept living space with string vaulted ceilings that create remarkable natural light throughout the living room, dining room and kitchen.The elegant living and dining rooms are anchored by a shared fireplace and seamlessly connect to a rooftop entertaining deck. The master suite opens directly to the rear balcony overlooking the resort style grounds. Luxurious primary suite features two oversized walk in closets, elegant trey ceiling and custom built-in cabinetry. The spa inspired bath features whirlpool jacuzzi, steam shower and rainfall shower head with custom finishes throughout. The lower level continues the home's exceptional design philosophy with an expansive recreation and entertainment area ideal for hosting family and guests. Media and Billiard room , Bar laundry.Three bedrooms with two full baths with direct access to deck and pool area. 1-1/2 garage featuring custom cabinetry featuring stainless steel countertops ,a mechanical room full size refrigerator and freezer plus dual wine refrigerators perfect for entertaining. The rear deck overlooks a koi pond transitioning to a spectacular pool area curated with tropical landscaping featuring a Heated unground swimming pool, Integrated spa , Cascading Waterfall ,Outdoor Kitchen,Custom bar, Outdoor Fireplace wifi throughout the property and integrated surround sound and media system . Beautiful custom shed finished off this rare village home ! A rare village home offering an exceptional combination of privacy , architectural character , resort-quality amenities, and one Port Jefferson Village's most desirable locations , 56 Old Homestead represents far more than a residence - its a private lifestyle destination. Every detail has been thoughtfully curated to deliver year-round luxury living and unforgettable entertaining in one of Long Island's most distinguished waterfront communities .

56 Old Homestead Road, Port Jefferson
$1,200,000
5 Beds ⋅ 4 Baths ⋅ 1032233 MLS
Golf players, Tennis lovers, Boaters & Beach goers! This sprawling 5 bedroom, 3.5 bath ranch that backs up to the lush, green Port Jefferson golf course is not just a house, it's a Lifestyle! A sunfilled open floor plan with vaulted ceilings & skylights leads to the family room with Fireplace and kitchen with breakfast bar. The sunken Living Room brings drama to the party, and the 2 Primary Suites, both with en suite baths, do not disappoint. A 3 Season Sunroom and 2 car garage complete the picture. Visit the Port Jefferson Village restaurants & boutiques for entertainment after a day at the Residents Only Beach and the Country Club, both just a stone's throw from your house! Close to the Marina, Stony Brook University, Hospitals, LIRR, and so much more. Professional photos coming soon.

30 Fairway Drive, Port Jefferson
$1,499,999
4 Beds ⋅ 3 Baths ⋅ 1026739 MLS
This 1920's Tudor is in the Private Community of Belle Terre, and Recently Updated. Large Panoramic Windows Throughout Overlook Nature & Water Views of Port Jefferson Harbor. The House Welcomes Warm Rays of Light through the Oversized Panoramic Windows throughout the Home and is Located on a Quiet Cul-De-Sac. This Home Boasts 3 1/2 Stories. 4 Beds. 2.5 Baths, and a Separate 3 car Garage. Brand New Roof w/transferrable warranty, Brand New Custom Windows, New Ductless Split Units throughout the Home for Heating and Cooling. Custom-Built Marble Fireplace. The Sliders Lead to the Large Deck Which Face the Beautiful Picturesque Harbor. Bedrooms and Livingroom Overlook the Beautiful Harbor and the Serene Nature of the Wooded Backyard. The Primary Offers Large Closets, & Sliders that Lead to the Rebuilt Upper Decks. A Newly Finished Ground Level Basement Boast a Bedroom/Office, Extra Living/Entertainment Room, Utilities, Laundry, Storage, and an Outside Entrance. Brand New Cesspool. This Home was Remodeled with True Thought, Detail, and Care. Easy Access to Harbor Right from the Home! Belle Terre Residents Amenities Offer: Direct Access to the Beach, Private Playground. Parks. Tennis Courts, and Community Center. PJ Yacht Club, Local to the Port Jefferson Village which offers Theatre, Restaurants, Nightlife, Art, and More., Connecticut Bridgeport Ferry only Minutes Away. 20 min Drive to Wineries, & Out East! This Home Speaks to You and is Truly One of a Kind.

11 Buena Vista Road, Port Jefferson
$1,000,000
4 Beds ⋅ 4 Baths ⋅ 1022843 MLS
MAJOR PRICE IMPROVEMENT! Welcome to this beautifully secluded residence in the prestigious Incorporated Village of Belle Terre, where privacy, comfort, and timeless North Shore living come together. Nestled on a serene, tree-lined property, this spacious four-bedroom home offers a rare opportunity to enjoy one of Long Island’s most sought-after waterfront communities. Designed for both everyday living and entertaining, the home features four generously sized bedrooms, two full bathrooms, two half bathrooms, and a charming wood-burning fireplace that creates a warm and inviting focal point. Sun-filled living spaces, an easy-flowing floor plan, and peaceful surroundings provide the perfect setting for relaxing or hosting family and friends. Belle Terre residents enjoy exclusive village amenities, including private beaches, waterfront parks, tennis courts, and a picturesque shoreline overlooking Port Jefferson Harbor. Just minutes away, the vibrant Village of Port Jefferson offers exceptional waterfront dining, boutique shopping, cafés, marinas, Harborfront Park, live entertainment, seasonal festivals, and the Bridgeport & Port Jefferson Ferry, providing convenient access to Connecticut. Ideally located near Stony Brook University, Stony Brook University Hospital, golf courses, yacht clubs, parks, nature preserves, and Long Island’s beautiful North Shore beaches, this home offers the perfect balance of peaceful seclusion and everyday convenience. Experience the charm, privacy, and exceptional lifestyle that make Belle Terre one of Long Island’s most desirable waterfront communities. This is a rare opportunity to make this special property your own.

21 Druid Hill Road, Port Jefferson
$1,375,000
4 Beds ⋅ 3 Baths ⋅ 1018546 MLS
Welcome to the ultimate country club lifestyle! This beautiful home is perfectly positioned across the street from the beautiful resident-only, West Beach! The backyard features a 20x40 salt water inground pool with all day sun exposure by the 11th hole of the prestigious Port Jefferson Country Club Golf Course! Hayward pool pump 2024, Jandy pool salt water system 2025, Jandy pool filter 2026, new pool Dolphin vacuum 2026. Everyday feels like a vacation! The home offers Brazilian Walnut wood floors on 1st floor, oak wood floors on 2nd floor and cedar floors in primary closets. Beautiful chefs kitchen with 48" Wolf Dual Fuel stove/oven (gas burners and griddle; electric oven), Wolf microwave, Bosch DW, GE Cafe refrigerator with hot water dispenser. Waterstone faucet w/lifetime warranty. American walnut center island 8.5" long! Natural stone inset above stove and island lighting: Honey Onyx Top of line Kingswood cabinetry (35 cabinets, 17 drawers!) 1st floor and 2nd floor laundry both equipped with Electrolux washer/dryer Primary bedroom bathroom: marble, Le Bain air massage tub (new control panel 2025) Full bathroom on 1st floor - Marble Central vacuum on all 3 levels Gas fireplace in den ADT alarm system 2024 Hard-wired speakers in LR: Polk, and backyard: Bose IPE Brazilian Walnut hardwood decking Rare opportunity to own a slice of paradise in one of the most coveted locations around, where the beach, golf, and resort-style living are all right outside your door! Conveniently located near 3 hospitals, university, LIRR, Ferry! Award winning Port Jefferson School District!

14 Fairway Drive, 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
$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
$2,100,000
4 Beds ⋅ 3 Baths ⋅ 1007135 MLS
Perched in the prestigious Belle Terre, this exceptional residence captures sweeping, unobstructed views of Port Jefferson Harbor and delivers a rare blend of refined luxury, privacy, and coastal elegance. Set on over two acres, this sprawling ranch has been thoughtfully reimagined to offer a seamless balance of modern sophistication and timeless design. From the moment you arrive, the home’s expansive setting and commanding water views create a lasting impression. Inside, soaring vaulted ceilings and walls of glass invite natural light. This is a full open-concept living environment. The dramatic double-sided fireplace anchors both the living and dining spaces, creating an ideal backdrop for both everyday living and elevated entertaining. The designer kitchen is nothing short of spectacular, appointed with premium appliances including a statement La Cornue range, exquisite Calacatta quartz surfaces, and an oversized island designed for gathering. A well-equipped butler’s pantry with prep sink and wine refrigeration enhances functionality while maintaining a polished aesthetic. The primary suite serves as a private retreat, offering tranquil water views, a custom inspired bathroom, and convenient access to laundry. Additional bedrooms are generously sized and thoughtfully positioned, while a sun-drenched bonus space provides flexibility for a home office, fitness studio, or serene lounge. The lower level extends the home’s living space with exceptional versatility, featuring a guest suite or office, summer kitchen, and an impressive theater room designed for a true cinematic experience. Sliding doors open to multiple outdoor living areas including an expansive Trex deck and hot tub, are perfectly oriented to take full advantage of the stunning waterfront backdrop. A newly constructed detached two-car garage with private EV charging station, along with modern systems including gas heat, central air, and whole-house generator, ensure both comfort and convenience. Located in Port Jefferson and offering access to the exclusive amenities of Belle Terre, this remarkable property presents a rare opportunity to own a turn-key harbor view retreat where every detail has been carefully considered and every view is unforgettable.

45 Bell Circle, 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
$2,399,000
5 Beds ⋅ 5 Baths ⋅ 1007146 MLS
Incorporated Vill. of Belle Terre , New Construction on flat 1 acre , 5 bedrooms 4.5 baths, 5000 sqft , winter water views, Grand 2 Story Entry, 9' ft First floor 8' 2nd floor with 10'6" tray ceilings, 9' basement w/ outside entrance, Cedar Impressions shingles,Limited Lifetime year Architectural Shingle & Standing Seam Roof, All Electrical Appliances, 6-7" Oak Flooring Throughout, UpGraded Moulding Package,Upgraded Electrical Package, 3zone Bosch Heat Pump HVAC W75 gal storage tank, system (qualified for tax abatement). White or Gray Shaker Kitchen Cabinets with Quartz Countertops, Double sided, Electrical Fireplace with Decorative Surround, Wraparound Covered Porch,Oversized 2 Car Garage, IGS, Sod Package with Green Screening, Asphalt Driveway w/ Stone walkway. NAIA Septic, Appliance Credit, Energy Star Home & Windows, ,2 Laundry Rooms, Maids Quarters,Oversized Closets, Electric Car Charger or One other extra choice from Contractor list. walk to PJ Village, Private Beach, **Time to customize**

18 Bell Circle, Port Jefferson
$1,185,000
5 Beds ⋅ 3 Baths ⋅ 1003873 MLS
Spacious & Gracious Colonial—set on 1.15 acres of beautifully maintained property, this classic residence offers the perfect blend of timeless design and modern comfort. With 5 spacious bedrooms and 3 full baths, this home is designed for both relaxed living and effortless entertaining. Thoughtfully renovated kitchen and bathrooms, gleaming oak floors, and recessed lighting create a warm, refined atmosphere throughout. The home has been lovingly cared for by its present owners who have accomplished many capital improvements offering a move-in-ready lifestyle leaving you more time to Enjoy! Step outside and discover your own private retreat: a serene backyard complete with lovely rear deck overlooking an in-ground pool and expansive green lawn—perfect for summer gatherings, quiet mornings, and a haven to return to at the end of the day where you can unwind and relax. Living in Belle Terre means embracing a lifestyle that feels worlds away—yet remains close to everything. • Peace & Privacy: A designated bird sanctuary, offering unmatched tranquility and natural beauty • Private Community Beaches & Parks: Enjoy exclusive access to scenic shoreline and green spaces • Amenities: Playgrounds, a community center, and a welcoming neighborhood atmosphere • Nearby Golf & Country Club in close proximity • Close to Port Jefferson Village: Boutique shopping, top-rated dining, and vibrant harbor front park From the moment you step inside 12 Deer Path in Belle Terre, you’ll understand what makes this offering truly special. You’re not just buying a home—you’re arriving at the lifestyle you’ve been waiting for.

12 Deer Path, Port Jefferson
$1,145,000
4 Beds ⋅ 4 Baths ⋅ 982299 MLS
Opportunity to reside in a sought after Village with private Beaches, Golf Course, award Winning Schools plus a ferry to Ct. This custom built home has an open floor plan with Seasonal Waterviews of LI Sound from the Great room, formal DR, and Master Bedroom. A Beautifully designed residence offers the perfect blend of comfort and convenience. new decking, new kitchen about 3-4 years old with walk-in pantry, 3 year old roof , energy efficient cast iron wood burning stove just to mention a few of the improvements ..wonderful retreat home is a short distance from PJV private East Beach and waterfront area on Crystal Brook Hollow Rd where Village residents have accessible racks for small boating recreational enjoyment.

7 Waterview Drive, Port Jefferson
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 969672 MLS
Welcome to this stunning new construction home located in an exclusive six-home subdivision in the heart of Port Jefferson Village. Tucked within one of the North Shore’s most sought-after communities, this private setting offers the charm and character of a coastal village that feels like a vacation destination year-round. This beautifully designed residence features approximately 3,500 square feet of living space, plus an additional 1,840-square-foot basement offering endless possibilities for recreation, storage, or future customization. The home includes 4 spacious bedrooms and 3.5 bathrooms, thoughtfully designed with modern living and comfort in mind. Enjoy the perfect blend of privacy, luxury, and village living—just moments from Port Jefferson’s vibrant harbor, shops, restaurants, and waterfront lifestyle.

Lot 6 Pine Hill Court, Port Jefferson
$3,950,000
8 Beds ⋅ 5 Baths ⋅ 843812 MLS
Nestled along the pristine shores of Port Jefferson Harbor, “The Cottage” a 5,800 square foot English Country Estate set on 3.85 lush waterfront acres with 530 feet of private beachfront is now for sale. Built circa 1906 as the private residence of Ralph Peters, former President of the Long Island Rail Road, the Estate has been preserved and restored as a master class in timeless early American craftsmanship and modern luxury. Step inside and be transported; this is not merely a home, but a living gallery. A reverent celebration of form and function, where flawless millwork and stained glass accents evoke a period era of workmanship. Diamond-pane windows framed with hand-finished grilles wrap the facade and invite natural light showcasing curated interiors filled with original artwork and antique furnishings. The heart of the residence is an awe-inspiring open concept grand room, crowned by a two-story atrium and 360-degree mezzanine. A massive central fireplace anchors the open concept space while the wrap around enclosed porch offers sweeping first-floor vistas of the Harbor, providing an unforgettable sensory experience. A dedicated first-floor study and formal dining room, each with their own fireplace, create a balance of intimacy and grandeur. The primary suite is an oasis featuring a resort-style full marble bath with oversized soaking tub. The home’s upper level, which includes a formal office and has a dedicated stairwell, offers additional bedrooms and bath, bringing the total for the house to eight bedrooms and four and a half baths. The homes lower level includes a changing room with dual showers, water closet, washer/dryer and direct outdoor access perfect for beach days. Aproned in cobblestone, the long private driveway, auto court and full roundabout provide access to a multi-level and terraced property that includes large sun deck and pergola overlooking the beach. A detached two-car garage complements a property designed and engineered with infrastructure and sustainability in mind. Retaining walls, terraces, patios, walkways and planters are constructed with the finest natural stone, cobblestone, crushed stone, slate and timber. A park-like property adorned in natural, mature perennials and blooming shrubs. A singular North Shore landmark in luxury, where history and heritage meet horizon on the bluffs of Belle Terre.

10 Pine Path, Port Jefferson
$1,200,000
L3591972 MLS

113 W Broadway, Port Jefferson

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.