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$639,990
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 a spacious walk-in closet and private 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
$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
$299,999
2 Beds ⋅ 1 Baths ⋅ 1044415 MLS
Why rent when you can own? Welcome to this light and bright 2nd-floor end-unit featuring 2 bedrooms and 1 full bathroom. Enjoy spacious rooms, a gas stove, in-unit washer and dryer, and central air conditioning just 3 years old. Step outside to your private fenced-in patio, perfect for relaxing or entertaining. Enjoy a fantastic community lifestyle with an array of amenities, including a clubhouse, in-ground pool, tennis court, fitness center, basketball court, and a separate children’s in-ground pool. A wonderful opportunity for comfortable living with plenty of recreation right at your doorstep!

84 Glen Hollow Drive, Port Jefferson
$375,000
2 Beds ⋅ 1 Baths ⋅ 1044360 MLS
Desirable end unit, Sagamore Hills Condominium Complex, 2 bedroom, (The primary bedroom is large and has ample storage) ,The second bedroom was originally a dining room, can be put back very easily, 1 full updated bathroom, large living room, Eat in kitchen, New floor molding, carpet, and raised panel doors. Newer windows, central air unit, gas heating system and gas water heater. Washer and dryer in unit. Amenities include, a clubhouse, tennis, basketball, pool, gym, and playground. Pet friendly. Private patio for your enjoyment. Close to shopping, Stonybrook hospital and University. True taxes are 3,633.75

145 Cambridge Drive, Port Jefferson
$799,000
3 Beds ⋅ 3 Baths ⋅ 1038494 MLS
Enjoy Panoramic Views Of Mt. Sinai Harbor, Cedar Beach & The Long Island Sound! Wake Up To Magnificent Sunrises Surrounded By Mature Woodlands From This 3 Bedroom, 2.5 Bath Monte Carlo Unit In The Sought-After Riviera Community, Boasting Spectacular Water Views From Nearly Every Room. Brimming With Potential And Ready For Your Personal Vision, This Home Offers An Incredible Opportunity To Update, Reimagine & Create Your Dream Space, Including The Possibility Of Opening The Floor Plan To Further Maximize The Breathtaking Views. The Second Level Features An Expansive Primary Suite With Walk-In Closet, Additional Double Closet & En Suite Bath. Two Generously Sized Additional Bedrooms Each Offer Walls Of Closets & Share A Full Hall Bath. Recent Improvements Include A New Heat Pump, Central Air Conditioning, Water Heater, 200-Amp Electric Service & Whole-House Generac Generator. Additional Features Include A One-Car Garage & Abundant Storage. Step Outside To A Large, Private Backyard With Patio & Stone Entertaining Areas, Offering A Tranquil Setting To Relax, Entertain & Take In The Incredible Water Views. This Is A Rare Opportunity To Create A Truly Special Home While Enjoying The Beauty Of Nature & The Ease Of Maintenance-Free Living. One Of The North Shore's Best-Kept Secrets, The Private Riviera Community Features Just 95 Units Set On 50 Wooded Acres & Offers A Saltwater Pool, Deeded Beach Rights, Maintenance-Free Living, Low Taxes, Port Jefferson Village Amenities, Discounted Golf & Tennis Membership & More. Just Minutes To Port Jefferson Village, Ferry, Hospitals, Dining, Shopping & Entertainment. Bring Your Vision & Make This Exceptional Property Your Dream Home! Don't Miss This Rare Opportunity To Make It Your Own! Town Of Brookhaven Taxes: $6,664.41. Port Jefferson Village Taxes: $864.48.

51 Rockledge Path, Port Jefferson
$1,300,000
3 Beds ⋅ 4 Baths ⋅ 1037285 MLS
Here is your opportunity to make an exquisite townhome with a water view of your own. Village Vista's is a 55 and better community located in the heart of Port Jefferson Village. Enter the home on the main level and look across the open floor plan and see the beauty of the Long Island Sound and the pastoral, peaceful views behind your home. This home boasts three comfortable levels with your own personal elevator, whole-house generator, a roll-up awning over the rear trex deck off the living room, Anderson windows and sliding doors throughout, and two fireplaces. To complete the splendor, the primary bedroom with an ensuite is located on the 1st floor. On the upper level, there are two additional bedrooms; one bedroom offers a sliding door to a trex deck. Also upstairs, there is a Jack & Jill bathroom and a comfortable loft with an eye-catching water view. This home also offers a coffered ceiling, paver driveway, and a two-car attached garage. The gourmet bright white kitchen has a large marble island, stainless steel appliances, and marble flooring. The lower level of this home is finished with a family room, full bathroom, laundry room, and a storage room. This home is an absolute gem and will not last.

35 Theresa Lane, Port Jefferson
$499,900
2 Beds ⋅ 3 Baths ⋅ 1034002 MLS
Highly desirable townhouse-style Clipper model featuring street-level entry and an attached garage for added convenience. This impeccably maintained home offers a spacious living room with sliding glass doors leading to a stunning paver patio surrounded by a privacy fence, creating the perfect outdoor retreat. The beautifully landscaped backyard provides an ideal setting for relaxing or entertaining. Both generously sized bedrooms feature en-suite full baths, including a primary suite with a vaulted ceiling and pull-down attic stairs for additional storage. A conveniently located second-floor laundry area adds to the home's functionality. Recent updates include a new hot water heater, garage door, refrigerator, dishwasher, and microwave, providing added value and peace of mind. Enjoy resort-style amenities including a pool, tennis courts, basketball court, and fitness center, along with all the benefits of Port Jefferson Village living, including private beach access, free village parking, and discounted Country Club membership. Ideally located just moments from Port Jefferson Village's marina, shops, restaurants, and entertainment, with the train station and Mather Hospital close by.

193 Windward Drive, Port Jefferson
$699,800
3 Beds ⋅ 2 Baths ⋅ 1032464 MLS
Welcome to 35 Timberline Circle, a beautifully updated, move-in ready three-bedroom, two-bath residence in the highly sought-after Riviera community of Port Jefferson. Offering the ease and convenience of one-level living, this exceptional home features a lovely open floor plan designed for both comfortable everyday living and elegant entertaining. The sun-drenched living space is highlighted by a cozy fireplace, expansive windows, and sliding glass doors that frame peaceful, scenic views while seamlessly blending indoor and outdoor living. Featuring a beautiful patio and inground sprinklers. Thoughtfully updated throughout with timeless finishes, this residence offers effortless style and comfort in one of the Riviera's most desirable locations, just moments from the community pool while maintaining a peaceful, private setting. Enjoy the best of Long Island living just moments from the waterfront charm of Port Jefferson Village, with its boutique shopping, renowned restaurants, marinas, beaches, parks, the Port Jefferson Ferry, the Long Island Rail Road, and Stony Brook University and Hospital. A rare opportunity to own one of the Riviera's most sought-after models in an exceptional location where luxury, convenience, and lifestyle come together beautifully

35 Timberline Circle, Port Jefferson
$670,000
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
$435,000
2 Beds ⋅ 2 Baths ⋅ 1028058 MLS
Welcome to this beautifully appointed second-floor end-unit condominium in the sought-after Highlands at Port Jefferson. This bright and inviting home offers the privacy and abundant natural light that only an end unit can provide. Beautiful custom moldings add timeless elegance throughout the living spaces, creating a warm and sophisticated atmosphere. The spacious primary suite features a private balcony overlooking the peaceful pond and sparkling community pool—the perfect setting to enjoy your morning coffee or relax at the end of the day. Ideally located just minutes from the charming Village of Port Jefferson, you’ll enjoy easy access to waterfront dining, boutique shopping, the ferry, marinas, parks, and year-round community events. Residents of The Highlands also enjoy exceptional amenities, including a clubhouse, fitness center, tennis courts, and a beautifully maintained pool. Whether you’re looking for a year-round residence or a low-maintenance retreat, this exceptional condominium offers comfort, convenience, and an unbeatable location. Property has a new electrical panel installed as well as a new railing for the deck overlooking the pond. Property being sold in as his condition.

88 Leeward Court, Port Jefferson
$309,000
2 Beds ⋅ 1 Baths ⋅ 1026789 MLS
Welcome to the sought after Stony Hollow Gated Community! This recently updated first floor two bedroom unit features brand new stainless steel appliances, captivating granite countertops, stylish vinyl flooring and two efficient wall AC units. The bathroom is completely renovated with brand new blinds throughout. Each bedroom offers spacious closets, complemented by additional storage in the hallway. The kitchen boasts sliding glass doors with built in blinds that opens to your expansive and private fenced patio with a large storage bin. Maintenance charges cover taxes, heat, gas for the stove, water, and an Optimum Silver cable package, alongside grounds upkeep, pool access and snow removal. Enjoy the community amenities, including an in ground pool, playground, picnic area, and BBQ facilities for your outdoor leisure. The complex is conveniently located near Stony Brook University, Stony Brook, Mather, and St. Charles Hospitals, with easy access to major roads, restaurants and shopping. Experience all that Stony Brook and Port Jefferson Villages have to offer. This unit is ready for you to make it your own!

460 Old Town Road Unit #3G, Port Jefferson
$759,000
4 Beds ⋅ 4 Baths ⋅ 1024562 MLS
Welcome to this beautifully updated, move-in-ready townhouse offering the perfect blend of comfort, style, and sophistication. This multi level home features 4 spacious bedrooms and 3.5 beautifully appointed baths, this meticulously maintained home has been freshly painted and thoughtfully updated throughout. The inviting floor plan boasts a spectacular oversized great room with a wood-burning fireplace, creating the perfect gathering space for family and friends. A second wood-burning fireplace adds warmth and charm to the private primary suite, which also features a relaxing jetted tub—your own private retreat at the end of the day. Additional highlights include: 2 car garage, central air conditioning, gas heat, central vacuum, custom moldings, freshly refinished wood floors as seen, high-hat lighting throughout, public sewers, a newer roof, siding, and driveway, along with numerous recent updates. Enjoy a low-maintenance lifestyle in this beautifully maintained community, where the monthly HOA takes care of professional landscaping and snow removal, allowing you more time to enjoy everything the area has to offer. Ideally located just minutes from the charming Village of Port Jefferson, you'll have easy access to waterfront dining, boutique shopping, marinas, beaches, year-round community events, ferry service to Connecticut, and the renowned John T. Mather Hospital and St. Charles Hospital. Commuters will also appreciate convenient access to major roadways and the Port Jefferson LIRR station. Offering exceptional space, modern updates, and an outstanding location in one of Long Island's most sought-after North Shore communities, this is more than just a home—it's a lifestyle. Don't miss this rare opportunity to own a townhouse of this caliber. Homes this beautiful don't last long! *This is a townhouse, not a condo. Homeowners are responsible for their own exterior maintenance on the structure. Landscaping, snow removal, trash pick up and road maintenance are included in the HOA fee.

6 Princess Tree Court, Port Jefferson
$649,999
2 Beds ⋅ 3 Baths ⋅ 1019153 MLS
Welcome to this beautifully maintained 2-bedroom, 2.5-bath home in The Highlands, featuring a versatile bonus room, beautiful hardwood floors, picturesque pond views, and numerous recent updates. The updated kitchen offers granite countertops, stainless steel appliances, gas cooking, and a Bosch dishwasher. French doors in the living room open to picturesque views of the backyard pond, creating a peaceful outdoor setting. The spacious primary suite features French doors, abundant natural light, an ample-sized closet, and a beautifully updated en-suite bathroom. Major mechanical updates include central air conditioning, a furnace, and a washer, all approximately six months old, along with a newer hot water heater. The primary bathroom and first-floor half bath were tastefully renovated in 2023-2024, with the primary bathroom featuring custom glass shower doors installed in 2024. Additional highlights include forced hot air heating, a gas fireplace, carpeting replaced approximately 2.5 years ago, a repaved driveway completed last year, and an attached garage with an automatic door opener. Enjoy the benefits of a low HOA that includes WiFi, cable, snow removal, garbage removal, access to a saltwater pool, fitness center, tennis courts, and more. Ownership includes access to two private village beaches, including a designated dog beach and West Beach, along with eligibility for discounted membership at the Port Jefferson Country Club. Offering numerous recent improvements, quality finishes, and an extensive list of amenities, this home combines comfort, convenience, and thoughtful updates throughout.

56 Leeward Court, Port Jefferson
$649,000
3 Beds ⋅ 3 Baths ⋅ 1011414 MLS
Welcome to the market this beautifully renovated 3-bedroom, 2.5-bath end-unit condo in the desirable Highlands community. Completely updated top to bottom in 2021, this move-in-ready home offers modern finishes, thoughtful upgrades, and exceptional privacy. The stunning redesigned kitchen features custom cabinetry, Quartz countertops, and GE Profile appliances, creating the perfect space for both everyday living and entertaining. The renovation extends throughout the home with all-new bathrooms featuring updated fixtures and flooring, custom closet organizers, and a convenient second-floor laundry area located just steps from the bedrooms. Additional premium upgrades include new flooring throughout, security alarm system, central vacuum, surround sound audio system, epoxy-coated garage floor, and pull-down attic stairs providing valuable additional storage space. As an end unit, the home enjoys extra natural light and offers a private, secluded patio ideal for relaxing or outdoor dining. Parking is plentiful with a one-car garage, driveway, and nearby guest parking. Residents of The Highlands enjoy access to outstanding community amenities including a pool, clubhouse, gym, and tennis courts. Located just minutes from the Port Jefferson train station, this home offers convenience for commuters while benefiting from low taxes that include all the amenities of Port Jefferson Village, including free village parking, access to resident only beaches and discounted membership opportunities at the Port Jefferson Country Club. This exceptional home combines modern upgrades, low-maintenance living, and an unbeatable location—don't miss the opportunity to make it yours.

213 Windward Court N, Port Jefferson
$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

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.