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$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
$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
$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
$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
$690,000
7 Beds ⋅ 4 Baths ⋅ 836072 MLS
Circa1890's rectory and original Barnum House now for sale! Possible 2 family home with proper permits. Needs TLC but some new mechanicals. Almost 4000 s/f of living space. 7/8 bedrooms, 4 fbths, 200 amp service, original white oak beams , coal chute in bsmt, spacious living areas, endless possibilities, walk to all in village. Perfect for those seeking a piece of history. Brookhaven Town Taxes approx $4k. Village taxes $3,699.15

127A Barnum Avenue, 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.