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217 Windward Court N, Port Jefferson
$499,990
2 Beds ⋅ 3 Baths ⋅ 1056103 MLS
Highly desirable Clipper model tucked away in a quiet corner of The Highlands featuring street-level entry, attached one-car garage, private driveway and nearby guest parking. Impeccably maintained with an open floor plan featuring a bright kitchen with breakfast bar open to the dining area and spacious living room with sliders to a beautiful paver patio and landscaped grounds—perfect for relaxing or entertaining. The second level offers two generously sized bedrooms, including a spacious primary suite with vaulted ceiling, his & hers double closets and en-suite bath, plus an additional bedroom, hall bath and convenient second-floor laundry. Enjoy low-maintenance living with community clubhouse, fitness center, saltwater pool, tennis, basketball and playground. Common charges include water, basic cable/WiFi, snow and garbage removal. Residents also enjoy Port Jefferson Village amenities including resident beaches, parks, free village parking and eligibility for discounted Port Jefferson Country Club membership. Just minutes to the Village, marina, shops, restaurants, train station and Mather Hospital. A wonderful opportunity to enjoy the best of The Highlands and the Port Jefferson lifestyle!

217 Windward Court N, Port Jefferson

16 Bridle Path Lane, Port Jefferson
$769,000
3 Beds ⋅ 2 Baths ⋅ 1054498 MLS
A Rare Find - Three Village School District Ranch in Port Jefferson, just 1 mile to the Village and Ferry. Welcome to 16 Bridle Path, a charming 3-bedroom, 2-bath, light-filled contemporary ranch built in 1982, set on a beautiful, level, private .52 acre in one of Port Jefferson’s most desirable neighborhoods. This home offers easy one-floor living. The expanded eat-in kitchen features granite countertops, high-end stainless appliances, and custom cabinetry. There are soaring vaulted ceilings in the living room and dining room, a marble fireplace, custom masonry driveway, 2-car garage, in-ground sprinklers, whole-house Generac Generator, Rheem Central Air Conditioning System (8 years), Anderson windows, 300-amp electrical service, and an electric car charging station The partially finished basement with an extra bath offers the perfect bonus space for a playroom, media area, home gym, or storage. Step outside to a large deck and wide, level yard ideal for gardening, entertaining under the covered gazebo, or simply enjoying peaceful outdoor living. The property feels open, usable, and inviting.

16 Bridle Path Lane, Port Jefferson

51 Norwood Avenue, Port Jefferson
$559,999
3 Beds ⋅ 2 Baths ⋅ 1046814 MLS
Welcome to 51 Norwood Ave, a charming home in the desirable Port Jefferson Station area. This well-maintained residence offers approximately 1,260 square feet of living space with a comfortable layout designed for everyday living and entertaining. All interior renovations were completed in approx 2020, featuring stainless-steel appliances, granite countertop, hardwood floors, LED overhead lighting, siding, roof, and renovated bathrooms. Enjoy a spacious backyard with beautiful patio with pavers, a private driveway which is great for parking large vehicles, and a detached one-car garage providing additional storage/parking. The home is located on a corner property so there backyard which is fully fenced wraps all the way around the house. The corner lot makes it ideal for parking any large trailers or RV. Plenty of space for pets! Plus, you are conveniently located near all the local shopping, dining, parks, and major roadways, this home offers a great combination of convenience and location. Super low taxes at 8.9K without any discounts!!!

51 Norwood Avenue, Port Jefferson

177 Cambridge Drive, Port Jefferson
$319,000
2 Beds ⋅ 2 Baths ⋅ 1052501 MLS
Enjoy comfort, convenience, and carefree living at 177 Cambridge Dr! This well-maintained Model offers 2 generously sized bedrooms, 1.5baths, a spacious living room, dedicated dining area, abundant closet space, and an in-unit washer and dryer. Carpeting was replaced with flooring approximately 9 years ago, the interior has been freshly painted, Bathroom had been recently updated and the private fenced patio creates the perfect spot to relax or entertain outdoors. Residents can enjoy an impressive selection of community amenities, including an in-ground swimming pool, clubhouse, fitness center, tennis, and pickleball courts, basketball court, playground, and beautifully maintained grounds. ideally situated within the Comsewogue school district with easy access to the LIRR, Hospitals, shopping, Dining, and major Roadway. It's A wonderful place to call Home!

177 Cambridge Drive, Port Jefferson

15 Cliff Road, Port Jefferson
$899,999
3 Beds ⋅ 3 Baths ⋅ 1050046 MLS
Tucked away at the end of a long driveway and perched on a private acre at the top of Belle Terre, this beautifully appointed rambling ranch offers privacy, serenity, and effortless one-level living just moments from the heart of Port Jefferson Village. With 3 bedrooms, 2.5 baths, and a spacious open floor plan, this home is designed to be enjoyed, shared, and filled with memories. The front porch welcomes you into an elegant entry foyer, where wood floors lead to a gracious formal living room anchored by a stunning stone-faced fireplace. Walls of windows fill the space with natural light, while the open formal dining room sets the stage for intimate dinners, holidays, and evenings with family and friends. Oversized sliders extend the entertaining outdoors to a private deck overlooking the mature, manicured property. The updated eat-in kitchen with large dining area features stone countertops, stainless steel appliances, gas cooking, and a door to a covered side porch. The primary suite offers an up-to-date en-suite bath, while 2 additional generously sized bedrooms, a full hall bath, powder room, and separate first-floor laundry complete the main level. A full, partially finished basement with fireplace provides endless possibilities and abundant storage, while a 2-car garage and extended driveway offer plenty of parking. Then there is life beyond the driveway. Port Jefferson Village offers a vibrant waterfront lifestyle with its harbor, restaurants, shops, live music, festivals, and year-round events, along with resident amenities including private beach access, tennis, pickleball, playgrounds, and more. The Long Island Ferry provides easy access to New England, while the LIRR connects you to NYC and beyond. Whether upsizing, downsizing, or simply dreaming of the ease of one-level living, here you can have space, privacy, and convenience without compromise. A home to gather in, an acre to retreat to, and a Village to become part of your next memories are waiting to be made. Total Taxes: $16,805 (Incl. Village Taxes $1933/Brookhaven $14,872)

15 Cliff Road, Port Jefferson

306 Liberty Avenue, Port Jefferson
$669,999
3 Beds ⋅ 4 Baths ⋅ 1050382 MLS
Set above the heart of Port Jefferson Village, this thoughtfully updated home is ready for its next chapter and a new owner to fill it with memories. Its gracious living areas provide a warm, welcoming backdrop for everything from quiet mornings at home to lively gatherings with friends. With 3 bedrooms and 3.5 bathrooms, the versatile floor plan offers room for a private home office with a separate entrance and parking, guest space, or a peaceful retreat. A full basement opens the door to even more possibilities, while a private backyard and patio with mature landscaping create space to entertain, unwind, and enjoy the seasons. Here, the Port Jefferson Village lifestyle becomes part of your everyday story. Begin the morning with coffee downtown, spend the afternoon walking along the harbor or relaxing at the beach, and end the day with dinner, live music, or a waterfront sunset. Charming boutiques, restaurants, marina, parks, transportation, and year-round community events are all just moments away, yet home feels comfortably tucked away from it all. More than simply a house, this is a place to settle in, make it your own, and create the moments that become lasting memories. Your next chapter in Port Jefferson Village begins here. The property has 2 tax bills - Total Brookhaven Taxes: $10,605 (lots .002 & .003), PJ Village Taxes: $678.21)

306 Liberty Avenue, Port Jefferson

203 Windward Court N, Port Jefferson
$625,000
3 Beds ⋅ 3 Baths ⋅ 1050644 MLS
Desirable 3-Bedroom Schooner Model in the sought-after Highlands community, ideally situated in the Village of Port Jefferson! Enjoy an incredible location within walking distance to the train station and just a quick stroll to Main Street’s popular restaurants, shopping, nightlife, and all that Port Jefferson Village has to offer. Move-in ready and beautifully updated throughout, this home features a recently renovated Eat-in Kitchen with gorgeous quartz countertops, crisp white shaker cabinetry, stylish subway tile backsplash, stainless steel appliances, and gas cooking. The desirable open floor plan is perfect for entertaining, featuring an oversized Living Room and Dining Area, along with additional counter seating ideal for casual dining and gatherings. The expansive Primary Suite offers an impressive private retreat, complete with two spacious walk-in closets and an en-suite bathroom. Additional updates and features include a new HVAC system with new condenser, all-new windows throughout, custom window treatments, two-panel interior doors, recessed lighting, convenient second-floor laundry, and a one-car garage. Tucked away in a quiet, dead-end location, the brick patio overlooks a peaceful, wooded setting, creating the perfect spot to relax and unwind. Enjoy resort-style community amenities including a swimming pool, tennis and basketball courts, clubhouse, and fitness center. A wonderful opportunity to enjoy low-maintenance living in one of Port Jefferson Village’s most convenient locations!

203 Windward Court N, Port Jefferson

250 N Country Road Unit #Single Family, Port Jefferson
$749,000
3 Beds ⋅ 2 Baths ⋅ 1050212 MLS
Welcome to 250 N Country Road, Port Jefferson, NY—a spacious ranch-style home situated on an impressive 20,000-square-foot lot. This inviting residence offers approximately 1,400 square feet of living space, featuring three bedrooms, two full bathrooms, seven rooms, and convenient single-level living. The home includes beautiful wood flooring, central air conditioning, Oil heating, a dedicated laundry room, and a full basement providing excellent storage and additional possibilities. A private driveway and attached two-car garage offer parking for up to five vehicles. Connected to public water and sewer, this property combines comfort, space, and convenience in a desirable Port Jefferson location. The expansive grounds provide outstanding potential for outdoor entertaining, gardening, recreation, or future improvements. Conveniently located near local shopping, dining, schools, transportation, medical facilities, and the attractions of Port Jefferson Village. A wonderful opportunity to own a well-positioned home with generous property and exceptional potential.

250 N Country Road Unit #Single Family, Port Jefferson

15 Hillcrest Avenue
$874,999
5 Beds ⋅ 4 Baths ⋅ 1048964 MLS
Welcome to 15 Hillcrest in Port Jefferson—a spacious Colonial offering a rare combination of multigenerational living and income-producing potential. The home features brand-new hardwood floors throughout, an open and inviting floor plan, a wood-burning fireplace, and a charming wraparound porch. Recent upgrades include a new gas heating system, new central air conditioning, and underground electrical service. Upstairs, you’ll find four generously sized bedrooms, a convenient laundry room, and an impressive primary suite featuring vaulted ceilings and a large walk-in closet. With flexible living space and a layout well suited for an additional income opportunity, this home offers versatility that is hard to find. Ideally located just minutes from Port Jefferson Village, the LIRR, shopping, dining, beaches, and all that the North Shore has to offer. A unique opportunity in a highly convenient Port Jefferson location!

15 Hillcrest Avenue

460 Old Town Road Unit #24-O, Port Jefferson
$199,999
2 Beds ⋅ 1 Baths ⋅ 1048650 MLS
Welcome to 460 Old Town Rd, Unit 24-0, located in the desirable Stony Hollow community-where comfort, convenience, and liftstyle come together! This beautifully updated 2-bedroom, 1 full bath second-floor co-op offers privacy with no neighbors above and the added benefit of being a corner unit, allowing for extra natural light and a more open feel. Renovated in 2021, the home features an updated kitchen, modern finishes, and all appliances replaced at the time-making it truly move-in ready. Inside, you'll find a spacious living room, a dedicated dining area, and a well-appointed kitchen designed for both everday living and entertaining. Stony Hollow offers an array of amenities for residents to enjoy, including on-site laundry facilities, an in-ground pool, basketball court, playground, and even a community vegtable garden-perfect for those who enjoy outdoor living and a sense of community. Conveniently located near shopping, dining, and major roadways, this is an excellent opportunity for comfortable and low-maintenance living. Don't miss your chance to own this bright, updated, and ideally located unit!!

460 Old Town Road Unit #24-O, Port Jefferson

24 Old Homestead Road, Port Jefferson
$789,999
3 Beds ⋅ 2 Baths ⋅ 1046868 MLS
A Port Jefferson Lifestyle Awaits in Harbor Hills. Prime location here in this 3 bedroom, 2 bathroom Cape, ideally situated in the desirable Harbor Hills community within the Incorporated Village of Port Jefferson. Set on a beautiful .57 acre property, the home features hardwood floors, a warm wood burning fireplace in the spacious living room, dining room, open kitchen with granite countertops & slider doors to the expansive Trex deck, 2 bedrooms and one full bath on the main floor. The upstairs primary suite offers a lovely ensuite bath, while the unfinished walk in attic provides exciting possibilities for additional living space, whether you envision a private home office, den, studio, or creative retreat. Beautifully landscaped property with belgium block walkway. 2 Car Garage, Full unfinished basement, Gas Heat, 200 Amp electric, Gutter Guards, CAC, and In Ground Sprinkers. Location is truly one of this home's greatest assets. Enjoy access to *two private beaches just a mile away*, along with discounted golf membership and the many amenities offered by the Village of Port Jefferson. Spend your days by the water, on the golf course, exploring the village, or simply enjoying the peace and privacy of your own backyard. Located within the renowned Port Jefferson Blue Ribbon School District and conveniently close to the LIRR and Stony Brook University, this home offers an ideal balance of community, convenience, recreation, and coastal living. Village taxes included Come discover why Port Jefferson isn't simply a place to live. IT'S A LIFESTYLE FOR A LIFETIME!

24 Old Homestead Road, Port Jefferson

31 Sands Lane, Port Jefferson
$800,000
4 Beds ⋅ 4 Baths ⋅ 1039000 MLS
Spacious colonial located on a quiet, sought-after street in the Harbor Hills Community. Featuring large rooms with a traditional layout, hardwood floors, new appliances, and a cozy den, this home has so much to offer. Upstairs includes 3 guest bedrooms, a full bath, a cedar closet, and a walk-in linen closet. The primary bedroom boasts an en-suite bath and a dressing room with both a double closet and a walk-in closet. The walk-out basement offers a game room, storage room, and a full bath, perfect for poolside use. Additional features include generator connection, upgraded 200-amp electric service, gas burner, and a 2.5-car garage with opener. The pool was open last season and will be available again for buyer inspection. Enjoy all village amenities, including private beaches, free parking, access to sports courts, and resident rates at PJCC.

31 Sands Lane, Port Jefferson

28 Block Boulevard, Port Jefferson
$650,000
4 Beds ⋅ 2 Baths ⋅ 1041140 MLS
Welcome Home To This Beautiful 4 Bedroom 1.5 Bath updated Splanch. This Home Offers A Warm and Inviting Atmosphere With Tasteful Updates Throughout. The Recently Remodeled Kitchen Features Clean White Shaker Cabinetry, Quartz Countertops, And Stainless Steel Appliances.The Formal Dining room Provides An Ideal Setting For Hosting Guests. The Den Is A Wonderful Place To Relax And Gather Around The Fireplace. Upstairs You'll Find Four Spacious Bedrooms With Beautiful Hardwood Floors And Plenty Of room For Everyone. The Updated Full Bathroom Features a Charming Farmhouse Inspired Design With Shiplap walls, Subway Tile, And Hexagon Tiled Flooring. This Home Also Offers A partial Basement Providing Flexible Space And A One Car Garage.Step Outside And Enjoy The Private Backyard With Approximately .34 Acres Offering Plenty Of Room To Relax Or Entertain. This Wonderful Home Is Ready To Welcome its Next Owners.

28 Block Boulevard, Port Jefferson

11 Soundview Drive, Port Jefferson
$999,999
4 Beds ⋅ 4 Baths ⋅ 1038126 MLS
Situated on one of Port Jefferson’s most sought-after blocks, this home radiates pride of ownership. Spacious rooms with oversized windows fill the home with natural light while mature plantings maintain privacy. The formal areas flow seamlessly indoors and out, perfect for entertaining. The custom kitchen boasts high-end cabinetry, newer appliances, radiant heat floors, dual ovens, and warming drawer. The expansive primary suite features two walk-in closets and a sun filled bathroom with vaulted ceilings. Upstairs, you’ll find a junior suite with private bath and another bedroom, bath and laundry. Additional 4th bedroom can be had on the 1st floor or with the legal bedroom in the basement. The private backyard includes an enclosed deck, patio, open lawn and fenced-in pool. The vinyl-lined L-shaped pool has an oversized shallow end and a deep end, surrounded by lush gardens and flowers. This home is at a mid-block location on a wide tree-lined street, just a half block from the golf course and a short distance to some of the village’s favorite private beaches. All village amenities. Taxes shown include both the Village of Port Jefferson and the TOB without any deductions.

11 Soundview Drive, Port Jefferson

149 Windward Court S, Port Jefferson
$660,000
3 Beds ⋅ 3 Baths ⋅ 1030359 MLS
Welcome to the largest unit in the highly desirable Highlands community! This beautifully updated corner unit offers exceptional space, privacy, and an impressive list of upgrades throughout. The bright and inviting interior features gleaming hardwood floors on the first level, a stunning renovated kitchen, and a spacious primary suite complete with a dedicated vanity area and an elegant frameless glass shower door. Thoughtful storage abounds with three linen closets, while new Andersen windows with a transferable warranty provide energy efficiency and peace of mind. Custom blinds are included with the home. Additional recent improvements include a new roof, a 2022 hot water heater and boiler, a new storm door, outdoor electrical outlets in both the front and rear of the home, and a beautiful Nicolock patio—perfect for relaxing or entertaining. Residents of The Highlands enjoy an outstanding resort-style lifestyle with exclusive amenities, including a private beach, clubhouse with fitness center, saltwater in-ground pool, tennis courts, and Port Jefferson Country Club golfing privileges. Additional benefits include free parking in Port Jefferson Village, making it easy to enjoy the area's renowned waterfront, dining, shopping, entertainment, and community events. Ideally located near St. Charles Hospital and Mather Hospital, this exceptional home combines comfort, convenience, and an unbeatable location. Don't miss this rare opportunity to own the largest unit in one of Port Jefferson's most sought-after communities!

149 Windward Court S, Port Jefferson

223 Old Post Road, Port Jefferson
$699,999
3 Beds ⋅ 2 Baths ⋅ 999888 MLS
Set on a beautiful hilltop property surrounded by mature trees, this updated 3-bedroom, 2 full bath Ranch offers privacy, natural light, and an unbeatable Port Jefferson lifestyle. Situated on over half an acre, the home features an open floorplan with hardwood floors throughout and sun-filled living spaces designed for comfortable everyday living and entertaining. The newly finished basement offers additional flexible living space with electric heat and an outside entrance through the attached 2-car garage. A new heat pump heating system helps offset oil expenses while adding year-round efficiency and comfort. Perfectly located just minutes from the historic shipbuilding Village of Port Jefferson, enjoy easy access to charming shops, restaurants, the Village Center, Harbor, and LIRR. Residents also enjoy exclusive Port Jefferson Village amenities including discounted country club membership, children’s programs, ice skating rink, tennis and pickleball courts and programs, plus the beloved Rocket Ship Park.

223 Old Post Road, Port Jefferson

87 Soundview 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

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.