ML# :3577512 Enjoy a Quintessential North Fork Summer at this Chic Cape at Pipes Neck Cove. Located Just Outside Greenport Village on a Quite Road Off the Beaten Path. The Home Boasts Beautiful Waterviews of the Cove from Nearly Every Window. The Enchanting Bay Beach is just a Stone’s Throw from the Home and is Truly One of the Most Special Locations on the North Fork. The Vast and Nearly Private Beach Overlooks Greenport Village and has Expansive Views of Shelter Island. The Cove is the Perfect Spot to Fish, or Explore by Kayak, Canoe or Paddleboard. A Mooring is Also Available if Interested. The Home Itself has an Open Yet Cozy Layout for Living and Dining. The Interior has been Thoughtfully Decorated to Create a Warm and Welcoming Atmosphere. Great For Entertaining or Lounging and Just Taking in the View. The Spacious Bedrooms are 2 Up and 2 Down to Accommodate All with a Full Bath on each Floor. The Vibrant Village of Greenport is Moments Away Where You will Explore Quaint Shops, Great Dining or Possibly a Ride on the Carousel! Make this Your Home Away from Home this Summer Season. You are Guaranteed to Fall in Love. Rental Permit #0957, Additional information: Appearance:Great
1545 Pipes Neck Rd, Greenport, NY, 11944
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
250 Osprey Nest Rd, Greenport, NY, 11944
ML# :806898 **2025 Rates:** May 23 - June 30: $18, 000; July: $20, 000; August 1 - Labor Day: $22, 000; Memorial Day - Labor Day: $55, 000Welcome to the 123 Sterling Boat Lofts! This exceptional property, situated on Sterling Harbor in the heart of Greenport Village, represents the perfect East End retreat. Thoughtfully designed with a spacious open floor plan, this third-floor corner unit offers stunning water views from every room, blending convenience with stylish flair. In addition to the loft, you will enjoy access to a private first-floor office space, complete with a lounge and home gym overlooking the bay and harbor. An exclusive boat slip is also included, accommodating a boat up to 30 feet in length. Don’t miss out on this remarkable opportunity—make it yours today!
123 Sterling Avenue Unit 12, Greenport, NY, 11944
ML# :3564418 2025 Rates: MDW-LD 105K, June $15K, July $35K, Aug-LD $45K Luxurious living in Greenport’s private Rock Cove Estates. A stone’s thi away to the deed private beach on the Long Island Sound. Highly desirable area where you can enjoy summer walks, lazy da the beach or gorgeous sunsets. Create memories to last a lifetime in this beautifully decorated home. Close to Greenport Village, restaurants, shopping, wineries, and recreational activities. Property
65 Rock Cove Court, Greenport, NY, 11944
ML# :3565265 Welcome to this spectacular waterfront home overlooking the Long Island Sound. This spacious 5000 sqft retreat features an open floor plan with four large bedrooms, 4.5 baths, and a versatile bonus room. Revel in breathtaking sunsets from nearly every room or the expansive back deck and patio. Amenities include a home gym, outdoor shower, multiple fireplaces, and beach access. Just a mile from Greenport Village’s charming shops and restaurants, this property offers the perfect blend of luxury and convenience for your ideal coastal getaway.
1250 Sound Drive, Greenport, NY, 11944
ML# :813226 Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village’s most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 8 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan. Additional information: Appearance: New
123 Sterling Avenue Unit 8, Greenport, NY, 11944
ML# :808230 Welcome to 485 Sutton Place, Greenport – a newly renovated gem that effortlessly combines modern luxury with timeless charm. Every detail of this stunning home has been thoughtfully designed to create a harmonious blend of comfort, style, and sophistication. Step inside to discover two sunlit levels of living. The first floor features two generously sized bedrooms and a full bathroom with tub. A bonus room with laundry and a kitchenette opens directly to the backyard, offering seamless indoor-outdoor living. Ascend to the second floor, where soaring ceilings and an open-concept layout invite you in. The stylish living room, complete with a cozy wood-burning fireplace, flows into the eat-in kitchen with island and dining area. From here, step onto the balcony for alfresco dining while overlooking the backyard oasis. This level also includes a sleek full bathroom with a walk-in shower, a spacious bedroom, and an en-suite retreat with its own half bath. The private backyard sanctuary is perfect for entertaining and unwinding. Take a dip in the brand-new 18x36 heated saltwater pool with elegant bluestone coping, ideal for enjoying throughout the summer and fall. The adjacent patio provides a shaded retreat for dining, while the fire pit area sets the scene for cozy evenings under the stars, complete with s’mores and cherished memories. Nestled on Long Island’s coveted North Fork, this home offers unparalleled access to the best of Greenport. Stroll less than a mile to the vibrant Greenport Village or explore the nearby Kontokosta Winery, a picturesque waterfront estate overlooking the Long Island Sound. Beach days are made easy with access to both private and public beaches just minutes away. Whether you’re seeking a summer getaway or a serene off-season retreat, 485 Sutton Place delivers the ultimate North Fork lifestyle. *Available for January-April ($12K/month), June ($20K), July ($30K), August-LD ($35K), September ($15K), October-December ($12K/month)*
485 Sutton Place, Greenport, NY, 11944
ML# :813208 Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village’s most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 2 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan., Additional information: Appearance: New
123 Sterling Avenue Unit 2, Greenport, NY, 11944
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
130 Tasker Lane, Greenport, NY, 11944
ML# :3494007 Love the beach ? Build your dream home on this beautiful land. Greenport is a 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 community.
620 Kerwin Boulevard, Greenport, NY, 11944