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    • Stunning Resort-Style Home with Modern Smart Features on the North Fork Discover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by tranquil Islands End public golf course, the popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. This neighborhood beach/park offers paddleboard and kayak stations along the marina, this home is perfect for embracing the North Fork’s outdoor lifestyle. As a state-of-the-art smart home, the apps provide remote access for lighting, heating, and air conditioning, music indoors and outdoors, and televisions strategically placed on the second floor, in the main living areas, and in a private TV room in the basement. The expansive floor plan offers not one, but two luxurious owner’s suites, one on the main level and another on the second floor, complemented by two additional bedrooms with private bathrooms. With a sleek, modern aesthetic, the home is thoughtfully designed for indoor-outdoor living. Outside, an elegant pool with a waterfall and evening lighting package becomes the centerpiece of the outdoor experience, complete with an option for an outdoor kitchen. Stunning dining area, and a lounge with a fireplace-perfect for entertaining or relaxing in style. This property brings the quality of its design and build to the forefront across all three levels, offering a flawless blend of comfort, functionality, and contemporary elegance. Indulge in this rare opportunity to own a slice of resort-like paradise on the North Fork., Additional information: Interior Features:Lr/Dr 74
      250 Osprey Nest Rd Greenport, NY 11944
      $3,799,999
      4 Bedrooms 5 Full Baths 2 Half Baths Sq. Ft. 5220.00:#
      Single Family For Sale ML# 3590145
      Stunning Resort-Style Home with Modern Smart Features on the North Fork Discover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by tranquil Islands End public golf course, the popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. This neighborhood beach/park offers paddleboard and kayak stations along the marina, this home is perfect for embracing the North Fork’s outdoor lifestyle. As a state-of-the-art smart home, the apps provide remote access for lighting, heating, and air conditioning, music indoors and outdoors, and televisions strategically placed on the second floor, in the main living areas, and in a private TV room in the basement. The expansive floor plan offers not one, but two luxurious owner’s suites, one on the main level and another on the second floor, complemented by two additional bedrooms with private bathrooms. With a sleek, modern aesthetic, the home is thoughtfully designed for indoor-outdoor living. Outside, an elegant pool with a waterfall and evening lighting package becomes the centerpiece of the outdoor experience, complete with an option for an outdoor kitchen. Stunning dining area, and a lounge with a fireplace-perfect for entertaining or relaxing in style. This property brings the quality of its design and build to the forefront across all three levels, offering a flawless blend of comfort, functionality, and contemporary elegance. Indulge in this rare opportunity to own a slice of resort-like paradise on the North Fork., Additional information: Interior Features:Lr/Dr
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: 631-765-3800, 631-404-2507, or  Email: Gerald Cibulski
    • Discover this stunning 2-year-old farmhouse in Greenport, where luxury meets timeless charm. With exquisite custom details throughout, this 4 BR, 3.5 BA home is crafted for relaxation and elegance. Savor expansive water views from multiple rooms and enjoy the professionally landscaped grounds. Unwind by your private saltwater pool surrounded by lush greenery. A bright, spacious home office offers sweeping views of Greenport’s waterways. Easy access to Pipes Cove Beach and fresh farm produce just around the corner enhances this pristine Peconic Bay Estates setting. Truly a North Fork gem!, Additional information: Appearance: Mint, Separate Hotwater Heater: Y 101
      3200 Bay Shore Rd Greenport, NY 11944
      $2,275,000
      5 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2600.00:#
      Single Family For Sale ML# 3591501
      Discover this stunning 2-year-old farmhouse in Greenport, where luxury meets timeless charm. With exquisite custom details throughout, this 4 BR, 3.5 BA home is crafted for relaxation and elegance. Savor expansive water views from multiple rooms and enjoy the professionally landscaped grounds. Unwind by your private saltwater pool surrounded by lush greenery. A bright, spacious home office offers sweeping views of Greenport’s waterways. Easy access to Pipes Cove Beach and fresh farm produce just around the corner enhances this pristine Peconic Bay Estates setting. Truly a North Fork gem!, Additional information: Appearance: Mint, Separate Hotwater Heater: Y
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: 631-765-3800, 631-384-5551, or  Email: Sheila Izzo
    • Unsurpassed opportunity. Private family compound or pampering hospitality venue minutes from downtown Hudson!. Exquisite estate on 100 park-like acres with historic 6000SF manor house, 2100SF guest cottage and a cavernous 7, 000 SF Barn structure. History shows that the famed Hudson River artist Frederic Church participated in the siting and construction of this impressive house which is a located near his own renowned masterpiece, Olana. The manor is an elegant, three story, stick style home with Catskill Mountain views and sunsets right out of the paintings themselves . Lovingly restored, the house has 7-Bedrooms (all with ensuite baths), spacious wrap around porch, floor to ceiling double front doors, impressive foyer with sweeping mahogany staircase, soaring 15 foot ceilings, hardwood floors and a swoon-worthy dining room off the foyer with a carved working fireplace, floor to ceiling windows, the largest is a Western facing mammoth plate glass window offering a masterpiece Catskill Mountain view. The kitchen is large and features a preserved red brick fireplace with woodbox. The first floor has high ceiling parlor rooms for libraries, music or winter gathering by a fire. There is a primary bedroom on the first floor wing with spa-worthy ensuite bathroom. This recently added wing provides an ADA compliant entrance off of a deck with a ramp. The storybook Guest Cottage, constructed in 2002, is ideal for caretaker or additional house guests, features a large open floor plan with 2-bedrooms each one with an ensuite baths. The easily customizable Pole Barn building offers endless opportunities as an entertainment venue, restaurant, private sports arena, gymnasium, art gallery space, vintage car collection display, etc. The long, winding entrance drive uphill leads to captivating walking trails, protected woodlands, picturesque stone walls and sweeping views in all directions. A mere two hours from New York City and minutes from the creative and entrepreneurial excitement of Hudson, New York and the Amtrak station. If you’re in need of a private compound with room to grow that is steeped in the rich history of the Hudson Valley, this is a gem. It’s reputation as a boutique hotel and wedding hospitality venues make it a strong choice to further grow a branded experience . And, the 100-acre parcel provides the perfect canvas for added expansion and development near Hudson! 36
      Greenport, NY 12534
      $7,330,000
      7 Bedrooms 7 Full Baths 1 Half Bath Sq. Ft. 6000.00:#
      Single Family For Sale ML# H6312196
      Unsurpassed opportunity. Private family compound or pampering hospitality venue minutes from downtown Hudson!. Exquisite estate on 100 park-like acres with historic 6000SF manor house, 2100SF guest cottage and a cavernous 7, 000 SF Barn structure. History shows that the famed Hudson River artist Frederic Church participated in the siting and construction of this impressive house which is a located near his own renowned masterpiece, Olana. The manor is an elegant, three story, stick style home with Catskill Mountain views and sunsets right out of the paintings themselves . Lovingly restored, the house has 7-Bedrooms (all with ensuite baths), spacious wrap around porch, floor to ceiling double front doors, impressive foyer with sweeping mahogany staircase, soaring 15 foot ceilings, hardwood floors and a swoon-worthy dining room off the foyer with a carved working fireplace, floor to ceiling windows, the largest is a Western facing mammoth plate glass window offering a masterpiece Catskill Mountain view. The kitchen is large and features a preserved red brick fireplace with woodbox. The first floor has high ceiling parlor rooms for libraries, music or winter gathering by a fire. There is a primary bedroom on the first floor wing with spa-worthy ensuite bathroom. This recently added wing provides an ADA compliant entrance off of a deck with a ramp. The storybook Guest Cottage, constructed in 2002, is ideal for caretaker or additional house guests, features a large open floor plan with 2-bedrooms each one with an ensuite baths. The easily customizable Pole Barn building offers endless opportunities as an entertainment venue, restaurant, private sports arena, gymnasium, art gallery space, vintage car collection display, etc. The long, winding entrance drive uphill leads to captivating walking trails, protected woodlands, picturesque stone walls and sweeping views in all directions. A mere two hours from New York City and minutes from the creative and entrepreneurial excitement of Hudson, New York and the Amtrak station. If you’re in need of a private compound with room to grow that is steeped in the rich history of the Hudson Valley, this is a gem. It’s reputation as a boutique hotel and wedding hospitality venues make it a strong choice to further grow a branded experience . And, the 100-acre parcel provides the perfect canvas for added expansion and development near Hudson!
      Presented By: Houlihan Lawrence, Inc  
      Call Today: 631.765.3800, or  Email:    
    • Step into this beautifully restored 1890s farmhouse, where timeless charm meets modern elegance. Curated by a professional design team, every inch of this home has been thoughtfully reimagined to blend its rich architectural heritage with a fresh, modern feel. Ideally located, the sun drenched home includes six bedrooms and 3 1/2 baths. Enter the first level, perfectly laid out with a fabulous chef’s kitchen with adjoining family room, a formal dining room, two fireplaces, and two dens. Hardwood floors and cathedral ceilings add to the charm. Access the private yard from the mud room off the kitchen to a spectacular backyard with a new, built-in outdoor kitchen, patio and fully fenced, refurbished, luxurious pool. The beautifully constructed pool house provides a stylish, functional space for guests or quiet retreat. Located in the heart of Greenport Village, just 300 feet from the sandy shores of the bay beach and adjacent to town and transportation, this home offers the perfect mix of convenience and tranquility. 30
      133 6th Street Greenport, NY 11944
      $3,450,000
      $2,999,000
      6 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3000.00:# Square Feet
      Single Family For Sale PRICE REDUCED ML# 810641
      Step into this beautifully restored 1890s farmhouse, where timeless charm meets modern elegance. Curated by a professional design team, every inch of this home has been thoughtfully reimagined to blend its rich architectural heritage with a fresh, modern feel. Ideally located, the sun drenched home includes six bedrooms and 3 1/2 baths. Enter the first level, perfectly laid out with a fabulous chef’s kitchen with adjoining family room, a formal dining room, two fireplaces, and two dens. Hardwood floors and cathedral ceilings add to the charm. Access the private yard from the mud room off the kitchen to a spectacular backyard with a new, built-in outdoor kitchen, patio and fully fenced, refurbished, luxurious pool. The beautifully constructed pool house provides a stylish, functional space for guests or quiet retreat. Located in the heart of Greenport Village, just 300 feet from the sandy shores of the bay beach and adjacent to town and transportation, this home offers the perfect mix of convenience and tranquility.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: 631.765.3800, or  Email:    
    • This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation. 21
      Greenport, NY 11944
      $2,100,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3500.00:#
      Single Family For Sale ML# 3579812
      This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: 631.765.3800, or  Email:    
    • Beautiful and rare new construction in the heart of historic Greenport. This stylish and spacious new build features four ensuite bedrooms, a semi-open floor plan, and stunning finishes. The first floor has a large chef’s kitchen with a breakfast nook, dining room, expansive great room, butler pantry, powder room, and walk-in kitchen pantry. A large vaulted primary suite is upstairs, with two additional ensuite bedrooms, laundry and an office landing. Over 3000 square feet of interior living space nestled on a quiet street, just two blocks from the village’s commercial center. 20
      424 2nd Street Greenport, NY 11944
      $1,850,000
      4 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Sale ML# 3577146
      Beautiful and rare new construction in the heart of historic Greenport. This stylish and spacious new build features four ensuite bedrooms, a semi-open floor plan, and stunning finishes. The first floor has a large chef’s kitchen with a breakfast nook, dining room, expansive great room, butler pantry, powder room, and walk-in kitchen pantry. A large vaulted primary suite is upstairs, with two additional ensuite bedrooms, laundry and an office landing. Over 3000 square feet of interior living space nestled on a quiet street, just two blocks from the village’s commercial center.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: 631.765.3800, or  Email:    
    • SELLER FINANCING AVAILABLE! Rare offering in high traffic location on the Main Rd in Greenport adjacent to Islands End Golf Course. This long standing restaurant establishment offers a turn-key opportunity with full kitchen, bar, 69 BOH approved seating, dining room, parking and equipment. Along with the commercial usage, this property also offers a 2 bedroom, 1 bathroom guest cottage. This location can see 40K+ cars pass by on a given summer day, so the road exposure is more than ideal. Whether you’re an end user looking to occupy the guest cottage while running the restaurant or an investor looking for ideal investment opportunities, this property will deliver. 28
      4545 Main Rd Greenport, NY 11944
      $1,795,000
      2 Bedrooms 1 Full Bath 2 Half Baths Sq. Ft. 2700.00:#
      Single Family For Sale ML# 3546866
      SELLER FINANCING AVAILABLE! Rare offering in high traffic location on the Main Rd in Greenport adjacent to Islands End Golf Course. This long standing restaurant establishment offers a turn-key opportunity with full kitchen, bar, 69 BOH approved seating, dining room, parking and equipment. Along with the commercial usage, this property also offers a 2 bedroom, 1 bathroom guest cottage. This location can see 40K+ cars pass by on a given summer day, so the road exposure is more than ideal. Whether you’re an end user looking to occupy the guest cottage while running the restaurant or an investor looking for ideal investment opportunities, this property will deliver.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: 631.765.3800, or  Email:    
    • This one-of-a-kind, mid-century modern was designed by renowned architect Claude Samton. Named Winged Weekend Flight, a wood hewn escape from city ways. When you enter, you will leave your worries behind. Incredible light and gorgeous landscape envelop this 3 bedroom, 1.5 bath sanctuary. Gunite pool with an automatic cover, Ipe decking and beach rights to a gorgeous sound front beach complement your experience. For cooler days, unwind by the fireplace after your evening beach stroll. Make this your refuge from everyday life!, Additional information: Appearance:Mint+, Interior Features:Lr/Dr 32
      2515 Sound Drive Greenport, NY 11944
      $1,695,000
      3 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 2290.00:#
      Single Family For Sale ML# 3579596
      This one-of-a-kind, mid-century modern was designed by renowned architect Claude Samton. Named Winged Weekend Flight, a wood hewn escape from city ways. When you enter, you will leave your worries behind. Incredible light and gorgeous landscape envelop this 3 bedroom, 1.5 bath sanctuary. Gunite pool with an automatic cover, Ipe decking and beach rights to a gorgeous sound front beach complement your experience. For cooler days, unwind by the fireplace after your evening beach stroll. Make this your refuge from everyday life!, Additional information: Appearance:Mint+, Interior Features:Lr/Dr
      Presented By: Corcoran  631-848-7730
      Call Today: 631.765.3800, or  Email:    
    • Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept kitchen seamlessly connects to the living room. Large bedrooms, convenient first-floor laundry and home office complete the interior. The breathtaking backyard steals the show, with a stunning inground pool perfect for hot summer days, lush landscaping ensures privacy, making the firepit area a perfect spot for unwinding and enjoying outdoor serenity. The private community beach offers peaceful moments by the water. This location is ideal for sunset strolls or weekend fun., Additional information: Appearance:very good 21
      130 Tasker Lane Greenport, NY 11944
      $1,475,000
      4 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3587176
      Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept kitchen seamlessly connects to the living room. Large bedrooms, convenient first-floor laundry and home office complete the interior. The breathtaking backyard steals the show, with a stunning inground pool perfect for hot summer days, lush landscaping ensures privacy, making the firepit area a perfect spot for unwinding and enjoying outdoor serenity. The private community beach offers peaceful moments by the water. This location is ideal for sunset strolls or weekend fun., Additional information: Appearance:very good
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: 631.765.3800, or  Email:    
    • This is your opportunity to watch your home be built from beginning to end. This 4 bedroom 3.5 bath has an en-suite bedroom/bath on the first floor and the second. Hardi-plank siding, Anderson windows, architectural roof shingles, hardwood floors throughout, quartz and or granite counters, and custom tile. Greenport is a quaint pedestrian friendly village filled with activities and opportunities like a deep-water marina, fishing excursions, Shelter Island Ferry, restaurants, shopping, movie theatre, Mitchell Park, carousel, galleries, golf course, and sound & bay beaches. Build your dream home in this beautiful beach community. Taxes represent land only. 16
      880 Kerwin Boulevard Greenport, NY 11944
      $1,450,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2604.00:# Square Feet
      Single Family For Sale ML# 3494242
      This is your opportunity to watch your home be built from beginning to end. This 4 bedroom 3.5 bath has an en-suite bedroom/bath on the first floor and the second. Hardi-plank siding, Anderson windows, architectural roof shingles, hardwood floors throughout, quartz and or granite counters, and custom tile. Greenport is a quaint pedestrian friendly village filled with activities and opportunities like a deep-water marina, fishing excursions, Shelter Island Ferry, restaurants, shopping, movie theatre, Mitchell Park, carousel, galleries, golf course, and sound & bay beaches. Build your dream home in this beautiful beach community. Taxes represent land only.
      Presented By: Daniel Gale Sothebys Intl Rlty  516-759-6822
      Call Today: 631.765.3800, or  Email:    
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