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$899,000
3 Beds ⋅ 4 Baths ⋅ 1011588 MLS
From the moment you pass through the gates and wind along the beautifully manicured streets, you know you've arrived somewhere special. A stunning slate and stone walkway welcomes you home, setting the tone for the elegance that awaits inside. Step through the front door and you're immediately greeted by soaring ceilings, streams of natural sunlight pouring through oversized transom- topped windows, and an open, airy floor plan designed for modern living. Every detail feels intentional, from the warm wood flooring underfoot to the soft glow of energy-efficient LED lighting installed during the home's complete 2021 renovation. The heart of the home is undoubtedly the chef-inspired kitchen, where family and friends naturally gather around the oversized center island. Gleaming white quartz countertops, a tumbled marble backsplash, custom glass-front cabinetry, and open shelving create a space that's as beautiful as it is functional. Whether hosting holiday dinners or enjoying a quiet morning coffee, this kitchen is built to be the backdrop of life's best moments. Just beyond, the expansive living room invites you to relax beside the cozy gas fireplace or open the sliders and step onto your private deck, the perfect place to unwind after a long day. The main-level primary suite offers a peaceful retreat, complete with a spa- like ensuite bath and generous closet space. Upstairs, two spacious bedrooms and a full bathroom provide comfort and privacy for family members or guests. Downstairs, the full basement offers endless possibilities—create a home office, fitness studio, recreation room, or guest suite. Combined with the attached two-car heated garage with epoxy flooring, this home delivers convenience without compromise, as well as being Generator ready. More than just a townhome, this is a lifestyle—one of comfort, elegance, security, and effortless living within a prestigious gated community. All that's missing is your next chapter.

21 Vantage Court, 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
$674,803
3 Beds ⋅ 3 Baths ⋅ 1001257 MLS
Discover exceptional value in the heart of Port Jefferson Village with this beautifully maintained 3-bedroom, 2.5-bath townhouse in the desirable Town & Country community. Offering nearly 1,900 square feet of living space, this move-in-ready home combines comfort, convenience, and coastal charm. The main level features a bright, open-concept layout with high ceilings, a cozy gas fireplace, and sliding glass doors that lead to a private deck with awning - perfect for relaxing or entertaining. Enjoy year-round comfort with central air, natural gas heating, and the added convenience of a private attached garage. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms designed for both functionality and comfort. Nestled within the meticulously maintained Town & Country community, residents enjoy beautifully landscaped grounds along with exclusive access to Port Jefferson Village amenities. Ideally located just minutes from charming shops, restaurants, waterfront parks, and the ferry, this home offers an unbeatable combination of space, location, and lifestyle.

36 Sea Court Lane, Port Jefferson
$899,000
3 Beds ⋅ 2 Baths ⋅ 1009847 MLS
Welcome to this custom-built brick ranch nestled on a beautiful 1.31-acre level lot in the highly desirable Belle Terre community of Port Jefferson and in the Highly desirable Port Jefferson School District. This home offers the perfect blend of quality construction, comfort, and potential. This well-maintained home is ready for its next chapter. The interior features an abundance of natural light streaming through beautiful Andersen windows, creating a warm and inviting atmosphere throughout. The kitchen was tastefully updated in 2016 & both bathrooms have been recently renovated, providing modern conveniences while maintaining the home's timeless appeal. Additional updates include a gas burner, CAC & HW heater, all replaced in 2016 & meticulously maintained. Other features include a new stove (2025), 200-amp electric service w/a back up generator hookup & CVAC. Residents of Belle Terre enjoy access to village amenities, private beaches, parks & the unique charm of Port Jefferson Village with waterfront dining, shopping, entertainment & ferry access. This property is being sold as-is and presents an excellent opportunity for buyers to add their own personal touches and build equity. The current pricing reflects improvements & updates that a new owner may wish to undertake. Seller wishes to disclose that an electrical fire occurred in the attic prior to their purchase of the home in 2014. During their ownership, they have experienced no issues related to this event. Additionally, during periods of heavy rain, water intrusion has been observed near a front basement window. Buyers are encouraged to conduct their own inspections and due diligence regarding all aspects of the property. The water intrusion may be related to grading around the window area, and buyers should discuss this with their home inspector.

42 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
$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
$425,000
1005293 MLS
One Acre of Land Ready to Build Your Port Jefferson Dream Home!! On a Private Cul de Sac. Famed Port Jefferson Schools, Private Beaches, Country Club and Beautiful Historic Walking Village!

105 Laurel Lane, Port Jefferson
$779,000
4 Beds ⋅ 3 Baths ⋅ 1005104 MLS
Updated and impeccably maintained 4BR/2.5Bth Colonial offering the perfect blend of comfort, quality and location. Enjoy a low-maintenance private backyard ideal for relaxing or entertaining without too much upkeep. Nestled near playgrounds, parks, elementary school, and fields! Wood burning fireplace and hardwood flooring. Media room has projector, screen, speakers or can be the DR. Primary w/ensuite bthrm. System 2000 Energy Kinetics oil burner! Port Jefferson School District! Note: Tax grievance in progress for 2026/2027.

600 Scraggy Hill Road, 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
$569,999
2 Beds ⋅ 3 Baths ⋅ 1004101 MLS
Welcome to easy living in the highly sought after Fox Meadow community. This beautifully maintained 2 bedrooms, 2.5 bath condo offers the perfect blend of comfort, style, and thoughtful upgrades throughout. Inside you will enjoy a spacious eat-in-kitchen featuring granite countertops, natural gas cooking, stainless steel appliances, a new microwave, and a new Bosch dishwasher, ideal for both everyday living and entertaining. Enjoy the added luxury of reverse osmosis and whole home water filtration system installed by Long Island Clean Water Service, providing crisp, clean drinking water throughout the home. The inviting living space is highlighted by a cozy wood-burning fireplace, creating the perfect atmosphere for relaxing evenings. Additional features include central air conditioning, forced hot air heat, and a 2023 hot water heater for peace of mind. Upstairs, convenience meets functionality with a washer and dryer located near the bedrooms, no need to carry laundry up and down stairs! The primary suite in this model is larger than other models offers a peaceful retreat with its own en-suite bathroom and 2 spacious walk-in closets. The second level also offers a versatile loft area, ideal for a home office, playroom, guest space or possible third bedroom. Pull down attic stairs provide easy access to additional storage space, while the attached 1 car garage adds even more convenience. Additional updates include stunning 2023 Pella doors and windows with built-in screens, bringing in abundant natural light while enhancing energy efficiency and convenience. Enjoy relaxing outdoors on your new private patio, the perfect setting for morning coffee or evening gatherings. Fox Meadow is a pet friendly community loaded with amenities including a clubhouse, salt water pool, playground, basketball courts, and tennis/pickleball courts, offering a true resort style lifestyle conveniently close to shopping, dining, transportation, and hospital. Move right in and enjoy all this exceptional home and community have to offer!

1405 Sara Circle, Port Jefferson
$750,000
3 Beds ⋅ 2 Baths ⋅ 995289 MLS
Welcome to 101 Red Oak Court, a beautifully updated 3-bedroom, 2-full-bath home tucked away on a quiet cul-de-sac in the desirable Harbor Hills Estates section of Port Jefferson Village. Set among mature trees, flowering landscape, stone walls, and a charming cedar-shake exterior, this home offers warmth, privacy, and the sought-after North Shore lifestyle. Inside, a welcoming foyer opens to light-filled living and dining spaces with hardwood floors, crown molding, soft neutral tones, and inviting natural views from nearly every window. The floor plan offers a comfortable living room, dedicated dining area, spacious open granite kitchen, breakfast nook, and three well-proportioned bedrooms, including a primary bedroom with convenient access to two full baths nearby. The kitchen and breakfast nook create an easy everyday flow, enhanced by a fireplace, skylight, and serene wooded backdrop. Outdoor living is a true highlight, with an expansive rear deck designed for entertaining, dining, relaxing, and enjoying the lush natural surroundings. A private driveway and attached garage add convenience. Located minutes from Port Jefferson Harbor, the Port Jefferson Ferry, train station, marinas, restaurants, and boutique shopping. Enjoy exclusive Port Jefferson Village amenities, including private village beaches, access to Port Jefferson Country Club with golf, tennis, dining, and water views, plus Village Constable services. Conveniently located near Mather Hospital, St. Charles Hospital, and Stony Brook University Hospital. A rare opportunity to enjoy comfort, charm, and the very best of Port Jefferson Village living.

101 Red Oak Court, Port Jefferson
$899,999
3 Beds ⋅ 4 Baths ⋅ 999137 MLS
Beautifully updated 3/4 bedroom home located in the desirable Harbor Hills section of Port Jefferson. This home has a great layout with plenty of space for everyday living and entertaining, while still feeling warm and inviting the second you walk in. The main level features vaulted ceilings, skylights, and tons of natural light. The updated kitchen includes granite countertops, shaker cabinetry, and luxury vinyl flooring with plenty of cabinet and counter space. The dining area with a wood burning fireplace and wet bar gives the home a really unique feel and makes it perfect for hosting family and friends. There is a large living area with tray ceilings and plenty of room to entertain, along with updated lighting and custom built ins throughout the home. The primary suite features a spacious walk in closet along with a bathroom complete with double vanity, soaking tub, separate shower, and skylight. The lower level offers even more flexibility with a possible 4th bedroom, updated bathroom, bonus room that can be used as a gym, office, or playroom, additional storage, and access to the 2 car garage. Outside, the home features a private level backyard with plenty of usable space for entertaining, relaxing, or future outdoor possibilities. Some major updates include updated HVAC with Goodman central air, 200 amp and electric with generator hookup. Located on a quiet cul-de-sac just minutes from private beaches,marinas, ferry, LIRR, shopping, and everything Port Jefferson Village has to offer.

105 Nadia Court, Port Jefferson
$799,999
4 Beds ⋅ 2 Baths ⋅ 994909 MLS
Welcome to this beautifully maintained 4-bedroom, 2-bath hi-ranch tucked away on a quiet cul de sac in the Village of Port Jefferson. This home offers flexible living spaces for multigenerational living, and a layout perfect for entertaining both outside and inside! Updates include hardwood flooring, stainless appliances, solid core doors and trim throughout, 200 amp electric panel with generator hook up, central air, heated in-ground salt water pool with hot tub surrounded by Trex decking, Anderson windows, and gas heating/cooking! The yard is made for those who love to entertain in the summer! Enjoy easy access to the village harbor, shops, and dining—all within the sought-after Port Jefferson School District.

21 Laurita Gate, Port Jefferson
$699,000
4 Beds ⋅ 2 Baths ⋅ 998411 MLS
Charming ranch nestled on a quiet country-like street offering peace, privacy, and easy one-floor living. Well maintained with newly finished wood flooring throughout and freshly painted walls. Bright and inviting layout with spacious living areas, wood burning fireplace, offering a private bedroom with ensuite bathroom and separate entrance. Great opportunity to enjoy the lifestyle of Port Jefferson's private beaches, golf course, and renowned school district!

3 Settlers Path, Port Jefferson
$699,999
4 Beds ⋅ 3 Baths ⋅ 982631 MLS
LOCATION is key here! This colonial with in ground pool is located on a DOUBLE cul de sac in the highly sought-after community of Harbor Hills in Port Jefferson Village. NOTE: Expected tax reduction of $3,400 annually. Close proximity to Stony Brook University, Stony Brook Hospital and Research center, Northwell Mather hospital, Saint Charles Hospital, and the picturesque harbor-front village just a stone's throw away. This is the ideal opportunity to experience the best of Long Island living that Port Jefferson has to offer, including private beaches, parking privileges, and top-rated blue ribbon schools. The main level hosts one primary bed with a private full bathroom, while an additional primary suite is on the upper level with a shared Jack and Jill bathroom. Upstairs also has hardwood flooring under carpet! With an in-ground pool featuring loop lock cover, two cozy fireplaces, gleaming hardwood floors, newer windows, and the convenience of gas on the block for future conversion, this home has it all. The roof was redone approx 2018 and the heating system was also updated in recent years. The extended driveway provides ample parking, and the meticulously maintained grounds showcase front and back inground sprinklers and a deck with pergola blooming with wisteria in the spring and summer for outdoor enjoyment. The versatile layout has been thoughtfully expanded and can be utilized to suit your living needs, whether you desire an optional home office, den, or recreational space - (wall in living room was closed and can be reopened).

107 Red Oak Court, Port Jefferson
$699,000
3 Beds ⋅ 3 Baths ⋅ 997206 MLS
Stunning, sun-filled 3 bedroom end unit condo in the most private location and ideal proximity to detached garage. Offering an updated kitchen, flowing hardwood floors, ample storage, private deck and balcony. The primary suite has large closet and en-suite bath. The full finished basement, with high ceilings, offers generous sized room, lots of storage, a laundry room and egress window. (Optional front load washer/dryer location on the 2nd floor.) Complex perfectly situated to offer natural surroundings, with mature plantings, all within 3 blocks of the downtown area. All village amenities. Taxes shown include both the town and the village. Both are eligible for approximately 5% reduction each. Floorplan and virtual tours available.

515 High Street Unit #18, Port Jefferson
$945,000
3 Beds ⋅ 2 Baths ⋅ 995805 MLS
Step into true elegance with this stunning circa 1940 gem, beautifully nestled on meticulously manicured grounds that invite you to relax and unwind. Surrounded by specimen plantings and enchanting foutains, this property offers a perfect blend of classic charm and modern luxury. Enjoy entertaning on your custom porch and generous paver patio complete with built-in BBQ and kitchen. Picture yourself in the 7-person hot tub under the stars! The enclosed back porch seamlessly brings the outdoors in, creating a delightful breakfast area that connects to the kitchen, both adorned with porcelian radiant heated tile. The home boasts Southern Yellow Pine floors throughout, enhancing its warm, inviting atmosphere. The primary bedroom and guest bedroom are on the 1st floor, and a 3rd bedroom is upstairs with an adjoining office/work space. With 2 updated baths, both with radiant heated floors, every detail has been thoughtfully designed for comfort. Recent upgrades include a new roof, new front & back doors, and fresh paint inside and out! The home is equiped with a Peerless cast iron boiler, whole-house water filter, and whole house generator for ultimate peace of mind. Enjoy the efficieny of natural gas for your dryer, oven/stove, and outdoor BBQ. The electric and plumbing systems have been upgraded and there is a Nest thermostat. Taxes are low! Stone's throw from Pt. Jefferson Village and all it has to offer, including restaurants, waterfront, ferry, shopping, and more. Amenties for this homeowner include private Beach Rights, free Village parking and more!

104 California Avenue, Port Jefferson
$499,000
3 Beds ⋅ 2 Baths ⋅ 996429 MLS
POTENTIAL RENTAL INCOME is included with this home (2 electric meters and off-street parking), which is nestled on a dead-end block in the Village of Port Jefferson. It is in the Comsewogue school district and includes all Port Jeff Village amenities: a year-round village parking permit, recreation programs for all ages, discounted Club golf and tennis memberships at the PJ Country Club, private resident beaches with seasonal lifeguards, and LIRR private parking. This home's main living area is on the 2nd floor, and it includes a lovely guest suite on the 1st floor, with the potential for an apartment for Mom or that kid who just won't leave home!!! It would also be a wonderful, separate, and sunny home office. This home is just 1 mile to LIRR, 2 miles from Port Jeff Ferry, Harbor, and Village Center. And only 8 miles to Stony Brook University and Hospital.

23 Woodside Avenue, Port Jefferson
$779,000
4 Beds ⋅ 3 Baths ⋅ 929763 MLS
Welcome to 101 Longfellow Lane, A Unique and Charming 4-5 Bedroom, 3 Bath, Double A-Frame Home Set in The Tree Tops of Port Jefferson with a Winter Waterview of Port Jefferson Harbor. Nature and Serenity Abounds Looking Out of the Floor to Ceiling Windows In this Creatively Designed Home. The Living/Dining Room is Accented by a Wood & Coal Burning Stove. Enjoy the Sights and Sounds of Nature from the Two-Level Wrap-Around Deck. A Spiral Staircase Leads You To Third Floor Bedroom Loft with Walk-in Closet and Full Bath. This Inviting Loft is Above the Triangular Wall of Windows, Offering Breathtaking Views, Year Round. The Lower Ground Level Offers a Separate Entrance With Two Bedrooms, Full Bath and Space for Office/Study or Gym. The Grounds Are Very Low Maintenance, A Gardener's Delight, Complete with a Potting Shed. Live In Nature's Beauty Among the Treetops in This Unique and Charming Home! A Short Walk To The Heart Of The Village! Beach Rights !

101 Longfellow Lane, Port Jefferson
$699,998
4 Beds ⋅ 3 Baths ⋅ 991204 MLS
BACK ON THE MARKET!!! Circa 1855, the Captain Lewis Tooker Home sits prominently in Port Jefferson Village, offering historic charm with thoughtful modern updates. Designed by architect Geysea Sarkkany, this residence features a chef’s kitchen equipped with a 6-burner Viking stove, cabinetry, and a center island, oversized walk-in pantry. Just off the kitchen is a large formal dining room, two formal living rooms with gas fireplace, and a flexible layout offering 3–4 bedrooms, including an office or optional fourth bedroom. Third floor Scenic views of Port Jefferson Harbor. Recent improvements include heating system upgrades with a new radiator and rebalanced lines for improved efficiency, concrete repairs to the rear chimney, and the addition of a gas line for a fireplace insert. Exterior updates include a widened driveway with new blacktop/Belgian block border, white PVC fencing with gate, and additional wood picket fencing along the side and rear. The home has been newly sided, and the roof is approximately 15 years old. Additional features include central air conditioning, separate hot water heater, a detached two-car garage and back yard patio. 2 blocks from shopping and events in Port Jefferson Village, residents enjoy access to village beaches, country club amenities, live music, seasonal festivals. TAX GRIEVANCE FILED

108 High Street, Port Jefferson
$879,000
4 Beds ⋅ 3 Baths ⋅ 986664 MLS
Just in time for summer living! You will love the inviting kidney shaped, heated inground pool, 36x16- ideal for relaxing or entertaining this season! On .51 landscaped acre with a detached 2-car garage. Freshly painted and beautifully refreshed, the home offers sun-drenched, generously sized rooms, with a kitchen designed to be the central gathering place! One bedroom on first floor and one full bath. The home has natural gas in the house; for heated pool, cooking. Roof is under 5 years, furnace is under 8 years. Pool liner under 6 years. Wireless 12 zone sprinkler system - The Port Jefferson Country Club is just minutes away for golf, tennis and PJ resident-only private beach. Renowned Port Jefferson School District. An exceptional find!

18 Pilgrim Drive, 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
$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
$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
$699,000
4 Beds ⋅ 3 Baths ⋅ 966593 MLS
GREAT OPPORTUNITY FOR YOU TO OWN AN INVESTMENT PROPERTY! Brand New Home- Less Than 5 Years Old! 4 Bedrooms/2.5 Baths; Low Taxes-Including Village Taxes; Open Kitchen w Granite Countertops & Stainless Steel Appliances; Lenox Equipment; Central Air; Private Driveway & 1 Car Garage; Natural Gas & Sewer; Stroll to Beautiful Historic Port Jefferson Village Private Beaches: Premier Country Club: Harborfront Park with Amazing Sunsets; Port Jefferson Village Center; Famed Port Jefferson Schools; Close to Trains, Buses, Ferry, Hospitals & StonyBrook University. A Must See! CLICK ON DOCUMENTS TO SEE SURVEY AND FLOOR PLAN

105 Liberty Avenue, Port Jefferson
$599,000
4 Beds ⋅ 3 Baths ⋅ 942446 MLS
This is a unique opportunity to purchase this spacious 9-room, 4-bedroom, 2.5-bath colonial home in Port Jefferson Village at an incredible price. The home features hardwood floors throughout, an in-ground pool with a loop loc cover, and a home office with a fireplace and an outside entrance, making it ideal for anyone who sees clients or works from home. This home is located just 1 mile from the Village Center. Village perks include exclusive resident access to beaches, tennis and pickleball courts, parks, and reduced membership fees at the Port Jefferson Country Club with an 18-hole golf course and clubhouse overlooking Mt. Sinai Harbor. The village is known for its waterfront festivals and concerts, restaurants and pubs, farmers markets, art exhibits, as well as mooring and dock rights, kayak racks, and proximity to the PJ train station (less than a mile), Stony Brook University and Hospital (6 miles), and the ferry to Connecticut. Explore all the village has to offer at: https://Portjeff.com/village-info. Taxes include the Village tax.

105 Rustic Road, Port Jefferson
$680,000
4 Beds ⋅ 4 Baths ⋅ 917170 MLS
Welcome to this spacious, well-designed bi-level home with 4 bedrooms and 3.5 bathrooms, complete with a basement, possible in home office, ample parking, and a private backyard — perfect for living or entertaining. Situated in Port Jefferson Village, you’ll enjoy the best of small-town coastal living while still being minutes from a vibrant downtown filled with boutiques, restaurants, and cultural spots along the harbor. The local public schools are highly rated, offering strong academics and a tight-knit community atmosphere and are in close proximity to this home. Residents benefit from easy access to waterfront parks, marinas, beaches, and a calendar full of community events and festivals — Pet owners, and anyone who values both a peaceful home base and an active village life. Parking for showings and open houses: there is a driveway that is accessible from Willis ave. Just before the corner of Liberty ave and Willis ave. Parking is available at the top of this driveway. Also street parking is available on Liberty ave just before and after the corner of Liberty ave and Fruita Street.

306 Liberty Avenue, Port Jefferson
$399,000
904412 MLS
Build the Home of Your Dreams in Port Jefferson Village! Rare opportunity to own a spacious .64-acre parcel in the heart of highly sought-after Port Jefferson Village. Nestled within Port Jefferson School District, this prime piece of residential land offers the perfect canvas for your custom dream home. Enjoy the convenience of being just moments from vibrant shops, charming restaurants, the Port Jefferson Ferry, and all the amenities this historic village has to offer. Don’t miss your chance to create a personal haven in one of Long Island’s desirable communities! Current Taxes are an estimate.

Dark Hollow Road, Port Jefferson
$899,000
4 Beds ⋅ 3 Baths ⋅ 842068 MLS
Beautiful colonial style home in Belle Terre community with close proximity to private North Shore LI Beach. Village of Belle Terre taxes are $2,500.00 annually, in addition to the Town of Brookhaven property taxes.

39 Cliff Road, Port Jefferson

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