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$1,060,000

Welcome to 3 Chuck Court, an exceptional 3,700 sq. ft. residence nestled in the heart of the Village of Port Jefferson, offering exclusive village amenities and a true lifestyle experience. This beautifully appointed home features 4 spacious bedrooms, each with its own private en-suite bath, plus a versatile 5th room ideal for a den, guest suite, or additional bedroom. A dramatic interior showcases coffered ceilings, rich stained hardwood floors, French doors, and a warm gas fireplace. The kitchen is designed for everyday living complete with 42” cabinetry, granite countertops, gas cooking, and stainless steel appliances Upstairs, enjoy a loft-style office space and a tremendous primary suite offering comfort and privacy. Additional highlights include walk-in closets, a mudroom with washer and dryer, attic storage with scuttle attic access, and smart home features such as Nest thermostats, smart bulbs, and security cameras. The home is also equipped with two-zone central air (including one new compressor) and two-zone gas heat with a 2016 boiler and separate hot water heater. The finished basement offers a gym and workshop, providing flexible bonus space. Step outside to your own private retreat featuring a stunning in-ground pool, pergola, lush landscaping, and in-ground sprinklers. As a Village of Port Jefferson resident, enjoy access to two exclusive resident-only east and west beaches along with preferential membership opportunities and reduced rates at the local country club. Commuters will appreciate residential preferred parking at the train station, as well as reserved parking spaces throughout the village. Pirates Cove offers six resident designated docking spaces available for use when open. All of this in a prime Village location, just moments from Port Jefferson’s vibrant harbor, dining, shopping, and waterfront attractions.

5 Beds ⋅ 4 Baths ⋅ 978424 MLS

Welcome to 3 Chuck Court, an exceptional 3,700 sq. ft. residence nestled in the heart of the Village of Port Jefferson, offering exclusive village amenities and a true lifestyle experience. This beautifully appointed home features 4 spacious bedrooms, each with its own private en-suite bath, plus a versatile 5th room ideal for a den, guest suite, or additional bedroom. A dramatic interior showcases coffered ceilings, rich stained hardwood floors, French doors, and a warm gas fireplace. The kitchen is designed for everyday living complete with 42” cabinetry, granite countertops, gas cooking, and stainless steel appliances Upstairs, enjoy a loft-style office space and a tremendous primary suite offering comfort and privacy. Additional highlights include walk-in closets, a mudroom with washer and dryer, attic storage with scuttle attic access, and smart home features such as Nest thermostats, smart bulbs, and security cameras. The home is also equipped with two-zone central air (including one new compressor) and two-zone gas heat with a 2016 boiler and separate hot water heater. The finished basement offers a gym and workshop, providing flexible bonus space. Step outside to your own private retreat featuring a stunning in-ground pool, pergola, lush landscaping, and in-ground sprinklers. As a Village of Port Jefferson resident, enjoy access to two exclusive resident-only east and west beaches along with preferential membership opportunities and reduced rates at the local country club. Commuters will appreciate residential preferred parking at the train station, as well as reserved parking spaces throughout the village. Pirates Cove offers six resident designated docking spaces available for use when open. All of this in a prime Village location, just moments from Port Jefferson’s vibrant harbor, dining, shopping, and waterfront attractions.

3 Chuck Court, Port Jefferson

$925,000

Don’t miss this rare opportunity to own a distinguished piece of Port Jefferson history. Originally built in 1890 for renowned sea captain Llewellyn Tuthill, this exceptional residence has been thoughtfully maintained and tastefully updated while honoring the craftsmanship and architectural character of its era. Set back and elevated above the roadway, the home commands attention with its stately presence and inviting wraparound porch. Inside, timeless period details abound, including soaring 10-foot ceilings, original custom woodwork, wide-plank flooring, antique push-button switches, decorative hardware, and beautifully restored cast-iron radiators. Stunning original pocket doors gracefully separate the living room from the entrance hallway, adding both architectural elegance and functional design rarely found today. Modern improvements blend seamlessly with the historic charm and include radiant heated flooring in the bathroom, a finished attic offering flexible bonus space, a newer roof, rebuilt chimneys, and a refinished fireplace. Ideally situated in the Historic Village of Port Jefferson, just moments from the harbor, village shops, dining, and amenities, and located within the highly regarded Port Jefferson School District—this is a truly special offering where history, character, and lifestyle come together.

4 Beds ⋅ 2 Baths ⋅ 949994 MLS

Don’t miss this rare opportunity to own a distinguished piece of Port Jefferson history. Originally built in 1890 for renowned sea captain Llewellyn Tuthill, this exceptional residence has been thoughtfully maintained and tastefully updated while honoring the craftsmanship and architectural character of its era. Set back and elevated above the roadway, the home commands attention with its stately presence and inviting wraparound porch. Inside, timeless period details abound, including soaring 10-foot ceilings, original custom woodwork, wide-plank flooring, antique push-button switches, decorative hardware, and beautifully restored cast-iron radiators. Stunning original pocket doors gracefully separate the living room from the entrance hallway, adding both architectural elegance and functional design rarely found today. Modern improvements blend seamlessly with the historic charm and include radiant heated flooring in the bathroom, a finished attic offering flexible bonus space, a newer roof, rebuilt chimneys, and a refinished fireplace. Ideally situated in the Historic Village of Port Jefferson, just moments from the harbor, village shops, dining, and amenities, and located within the highly regarded Port Jefferson School District—this is a truly special offering where history, character, and lifestyle come together.

204 Myrtle Avenue, Port Jefferson

$825,000

Incredible opportunity to own a magnificent Colonial in the highly sought-after Harbor Hills section of Port Jefferson Village, perfectly positioned at the back of a quiet cul-de-sac with sweeping green space to the right creating a setting that feels private, peaceful, and expansive; this rare .58-acre usable property is set back with a long blacktop driveway, two-car attached garage, full at-grade basement with recessed lighting, and an incredible multi-level paver patio built for next-level entertaining; step inside to an open floor plan filled with natural light, recessed lighting in the kitchen, gleaming hardwood floors, a formal living room, and a breathtaking den/great room centered around a cultured stone wood-burning fireplace, while the first floor also offers a powder room and a mudroom with custom-built cubbies and lockers that blend function with style, and front loading washer and dryer with additional cabinet space, the chef’s kitchen with tile backsplash and undercabinet lighting flows beautifully into the formal dining room with chandelier and hardwood floors and features tile flooring, white cabinetry, granite countertops, stainless steel appliances, a long center island with range top, pendant lighting and seating area, double ovens, and sliders leading directly to the custom patio; upstairs you’ll find an enormous primary suite wing with hardwood floors, vaulted ceilings, walk-in closet with closet system, and a full bath with walk-in stand-up shower, along with additional spacious bedrooms and a spotlight Jack-and-Jill hallway bath with glass tub and stand-up shower; complete with 200-amp electric and located in the Port Jefferson School District with deeded beach rights, this is the kind of home that checks every box—privacy, property size, layout, and location—all wrapped into one exceptional offering in Port Jefferson Village.

4 Beds ⋅ 3 Baths ⋅ 965400 MLS

Incredible opportunity to own a magnificent Colonial in the highly sought-after Harbor Hills section of Port Jefferson Village, perfectly positioned at the back of a quiet cul-de-sac with sweeping green space to the right creating a setting that feels private, peaceful, and expansive; this rare .58-acre usable property is set back with a long blacktop driveway, two-car attached garage, full at-grade basement with recessed lighting, and an incredible multi-level paver patio built for next-level entertaining; step inside to an open floor plan filled with natural light, recessed lighting in the kitchen, gleaming hardwood floors, a formal living room, and a breathtaking den/great room centered around a cultured stone wood-burning fireplace, while the first floor also offers a powder room and a mudroom with custom-built cubbies and lockers that blend function with style, and front loading washer and dryer with additional cabinet space, the chef’s kitchen with tile backsplash and undercabinet lighting flows beautifully into the formal dining room with chandelier and hardwood floors and features tile flooring, white cabinetry, granite countertops, stainless steel appliances, a long center island with range top, pendant lighting and seating area, double ovens, and sliders leading directly to the custom patio; upstairs you’ll find an enormous primary suite wing with hardwood floors, vaulted ceilings, walk-in closet with closet system, and a full bath with walk-in stand-up shower, along with additional spacious bedrooms and a spotlight Jack-and-Jill hallway bath with glass tub and stand-up shower; complete with 200-amp electric and located in the Port Jefferson School District with deeded beach rights, this is the kind of home that checks every box—privacy, property size, layout, and location—all wrapped into one exceptional offering in Port Jefferson Village.

120 Alden Drive, Port Jefferson

$799,000

Located on a quiet cul-de-sac in the Harbor Hills Estates section of Port Jefferson Village, this beautifully updated 4 bedroom, 4 full bath home offers the ideal combination of space, comfort, and the highly sought-after Port Jefferson Village lifestyle on Long Island’s North Shore. The first level features three bedrooms, including one with its own ensuite bathroom, perfect for guests or extended living. The kitchen features soaring ceilings, skylights, and a wood-burning fireplace, creating a bright and inviting space that flows out to the multilevel deck, ideal for entertaining or relaxing at home. A finished basement with a wine cellar provides additional living and entertaining space. The second level is dedicated to the private primary suite, featuring a spacious bedroom, large closet, and a spa-inspired bathroom with double sinks, a soaking tub, and a walk-in shower with rain head. When the trees are in full bloom, the primary suite offers the unique feeling of living in your own private treehouse retreat. Located in the heart of Port Jefferson Village, this home is just minutes from Port Jefferson Harbor, the Port Jefferson Ferry, Port Jefferson train station, marinas, restaurants, and boutique shopping. Enjoy exclusive Port Jefferson Village amenities, including private village beaches, access to the Port Jefferson Country Club with golf, tennis, dining, and stunning water views, as well as dedicated Village Constable services, adding an extra level of privacy and peace of mind. Conveniently located near three major medical centers—Mather Hospital, St. Charles Hospital, and Stony Brook University Hospital—this is a prime opportunity to experience the very best of the North Shore Long Island lifestyle in Suffolk County.

4 Beds ⋅ 4 Baths ⋅ 968886 MLS

Located on a quiet cul-de-sac in the Harbor Hills Estates section of Port Jefferson Village, this beautifully updated 4 bedroom, 4 full bath home offers the ideal combination of space, comfort, and the highly sought-after Port Jefferson Village lifestyle on Long Island’s North Shore. The first level features three bedrooms, including one with its own ensuite bathroom, perfect for guests or extended living. The kitchen features soaring ceilings, skylights, and a wood-burning fireplace, creating a bright and inviting space that flows out to the multilevel deck, ideal for entertaining or relaxing at home. A finished basement with a wine cellar provides additional living and entertaining space. The second level is dedicated to the private primary suite, featuring a spacious bedroom, large closet, and a spa-inspired bathroom with double sinks, a soaking tub, and a walk-in shower with rain head. When the trees are in full bloom, the primary suite offers the unique feeling of living in your own private treehouse retreat. Located in the heart of Port Jefferson Village, this home is just minutes from Port Jefferson Harbor, the Port Jefferson Ferry, Port Jefferson train station, marinas, restaurants, and boutique shopping. Enjoy exclusive Port Jefferson Village amenities, including private village beaches, access to the Port Jefferson Country Club with golf, tennis, dining, and stunning water views, as well as dedicated Village Constable services, adding an extra level of privacy and peace of mind. Conveniently located near three major medical centers—Mather Hospital, St. Charles Hospital, and Stony Brook University Hospital—this is a prime opportunity to experience the very best of the North Shore Long Island lifestyle in Suffolk County.

108 Dogwood Road, Port Jefferson

$720,000

OPEN HOUSE CANCELLED SUNDAY DUE TO SEVER WEATHER! Discover your dream home nestled in a serene cul-de-sac within the highly coveted Village of Port Jefferson. This lovely large ranch offers the convenience of one-story living, featuring original details that create a warm and inviting atmosphere. With a thoughtful layout, you’ll find both primary and guest bedrooms conveniently located on the first floor, complemented by beautiful wood floors throughout.This property presents a blank canvas, inviting you to add your personal touches and make it truly your own. The oversized full basement includes a garage at the basement level, providing ample storage and versatility.Step outside to your private woodland lot, complete with an inviting in-ground pool, perfect for colling off on those hot summer days. Enjoy the vibrant lifestyle of Port Jefferson, just seconds away from charming village shopping, exciting restaurants, the ferry, and mass transportation options.Seize the opportunity to live in a bustling summer downtown, where picturesque scenery and a vibrant community await you. Don't miss out on this exceptional home!

3 Beds ⋅ 3 Baths ⋅ 959457 MLS

OPEN HOUSE CANCELLED SUNDAY DUE TO SEVER WEATHER! Discover your dream home nestled in a serene cul-de-sac within the highly coveted Village of Port Jefferson. This lovely large ranch offers the convenience of one-story living, featuring original details that create a warm and inviting atmosphere. With a thoughtful layout, you’ll find both primary and guest bedrooms conveniently located on the first floor, complemented by beautiful wood floors throughout.This property presents a blank canvas, inviting you to add your personal touches and make it truly your own. The oversized full basement includes a garage at the basement level, providing ample storage and versatility.Step outside to your private woodland lot, complete with an inviting in-ground pool, perfect for colling off on those hot summer days. Enjoy the vibrant lifestyle of Port Jefferson, just seconds away from charming village shopping, exciting restaurants, the ferry, and mass transportation options.Seize the opportunity to live in a bustling summer downtown, where picturesque scenery and a vibrant community await you. Don't miss out on this exceptional home!

115 Red Oak Court, Port Jefferson

$670,000

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.

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

$600,000

Step into luxury and lifestyle with this fully renovated Bracken-built townhouse, ideally located in the heart of Port Jefferson Village. No expense was spared in this meticulous remodel: showcasing 2x6 construction, elegant refinished hardwood floors throughout, and custom millwork including handcrafted stair rails and moldings. The brand-new kitchen features Frigidaire Gallery Series appliances, ceramic tile flooring, and sleek Silestone countertops. All bathrooms have been gutted and reimagined with Hans Grohe fixtures and new Velux skylights, offering spa-like serenity. Enjoy seamless indoor-outdoor living with new energy-efficient entry doors, Andersen screen doors, and TimberTech decking in both the front and rear — perfect for relaxing with courtyard views. Recent upgrades include two replaced heat pumps, new sliding glass doors, and enhanced insulation for year-round comfort. Brand new custom window shades though out. Village Perks & Lifestyle Live where others vacation — with exclusive resident access to beaches, tennis and pickleball courts, parks, live theater, waterfront festivals, farmers markets, art exhibits, and the vibrant Village Center. Enjoy renowned Port Jefferson schools, mooring and dock rights, kayak racks, and proximity to the PT train station (less than a mile), three major hospitals, and the ferry. This isn’t just a home — it’s a gateway to a new lifestyle. Explore all the village has to offer at :https://Portjeff.com/village-info

2 Beds ⋅ 3 Baths ⋅ 961706 MLS

Step into luxury and lifestyle with this fully renovated Bracken-built townhouse, ideally located in the heart of Port Jefferson Village. No expense was spared in this meticulous remodel: showcasing 2x6 construction, elegant refinished hardwood floors throughout, and custom millwork including handcrafted stair rails and moldings. The brand-new kitchen features Frigidaire Gallery Series appliances, ceramic tile flooring, and sleek Silestone countertops. All bathrooms have been gutted and reimagined with Hans Grohe fixtures and new Velux skylights, offering spa-like serenity. Enjoy seamless indoor-outdoor living with new energy-efficient entry doors, Andersen screen doors, and TimberTech decking in both the front and rear — perfect for relaxing with courtyard views. Recent upgrades include two replaced heat pumps, new sliding glass doors, and enhanced insulation for year-round comfort. Brand new custom window shades though out. Village Perks & Lifestyle Live where others vacation — with exclusive resident access to beaches, tennis and pickleball courts, parks, live theater, waterfront festivals, farmers markets, art exhibits, and the vibrant Village Center. Enjoy renowned Port Jefferson schools, mooring and dock rights, kayak racks, and proximity to the PT train station (less than a mile), three major hospitals, and the ferry. This isn’t just a home — it’s a gateway to a new lifestyle. Explore all the village has to offer at :https://Portjeff.com/village-info

515 High Street Unit #10, Port Jefferson

$589,500

Step into a delightful blend of classic charm and modern convenience with this beautifully updated Cape Cod home! Located just one block from vibrant Port Jefferson Village, you'll enjoy easy access to boutique shops, delicious restaurants, and the picturesque harbourfront. The New Kitchen has just been updated with maple cabinets, quartz countertops, and stainless steel appliances. A beautiful New Full Bath, all New Windows, updated electric panel and new flooring throughout complete the picture. A lovely yard and detached 2 car garage with new garage door make this one something Very Special! All Port Jefferson Amenities included, resident-only beach rights too! Very low Taxes.

2 Beds ⋅ 1 Baths ⋅ 934136 MLS

Step into a delightful blend of classic charm and modern convenience with this beautifully updated Cape Cod home! Located just one block from vibrant Port Jefferson Village, you'll enjoy easy access to boutique shops, delicious restaurants, and the picturesque harbourfront. The New Kitchen has just been updated with maple cabinets, quartz countertops, and stainless steel appliances. A beautiful New Full Bath, all New Windows, updated electric panel and new flooring throughout complete the picture. A lovely yard and detached 2 car garage with new garage door make this one something Very Special! All Port Jefferson Amenities included, resident-only beach rights too! Very low Taxes.

122 Liberty Avenue, Port Jefferson