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
2515 Sound Drive, Greenport, NY, 11944
ML# :805303 Winter Getaway in Historic Greenport. Experience the charm of this renovated 1920’s Village Craftsman featuring the perfect combination of vintage charm with modern comforts and style. First floor includes cozy living room, dining room, full bath, newly renovated kitchen and sitting area. Three light filled bedrooms are located on the second floor with full bath. Close to the heart of downtown Greenport Village, with easy access to shops, restaurants, and waterfront activities. Available for an off season rental until May 15, 2025. Permit #G24-002
324 5th Avenue, Greenport, NY, 11944
ML# :806288 Charming 1920’s recently renovated bright and airy cottage features an office/den, an open concept living room/eat in kitchen with vaulted ceilings and a 2nd floor bedroom. The fully fenced backyard offers a lovely large deck for entertaining, lush mature landscaping and picturesque vineyard views. Iconic 67 Steps sound beach is just moments away at the end of the block. Close to everything you would need or desire living on the NF! Village Life at its best: Restaurants, Shopping, Vineyards, Transportation, Marinas and so much more!
34 Sound 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# :804495 Public RemarksNewly Renovated Waterfront Unit with Spectacular Views Of Bay, Beach, Shelter Island and Beyond. Spacious Owner’s Suite with Full Bath and Private access to Bayfront Deck. Second Bedroom and bath are both generously sized. Entire unit is Elegantly Styled. Waterfront Balcony On Beach. Open plan living, dining and kitchen with views from every window. Living room has wood burning fireplace with sliders leading to full width bayfront deck. Hardwood and ceramic tile flooring, all new stainless steel appliances. Complex has a Waterfront Pool, Tennis & Pickle Ball Courts, Marina and Over 200 Ft of sandy private Bay Beach. Ownership Includes a Boat Slip in Marina. In Heart Of Greenport Village. Close To Restaurants, Transportation, Ferry & Shops. Appearance:Mint
160 5th Unit 12, Greenport, NY, 11944
ML# :803911 Welcoming Greenport Village Storefront with Large Windows and Full Glass Entry Door Provide Great Visibility! Two Updated Rooms plus Updated 1/2 Bath. Front and Side Doors Entrances. Central Airconditioning.
137 Front Street, Greenport, NY, 11944
ML# :806898 2025 Rates: $55K for MDW-LD. Welcome to the 123 Sterling Boat Lofts. This unique offering located on Sterling Harbor locsted in the center of Greenport Village is the perfect Village retreat. Incredibly well appointed with wide open floor plan and water-views from every room, this unit will offer the convenience and with a touch of stylistic flare. In addition to thids 3rd floor corner unit w/ elevator accommodations, you will have access to an additional private first floor office unit equipped with lounge and home gym over looking the bay and harbor, along with a private boat slip that can accommodate a 30’+ boat. Do not let this incredible offering slip away!
123 Sterling Street Unit 12, Greenport, NY, 11944
ML# :3558855 GREENPORT OYSTER POINT WATERFRONT CONDO WITH BOAT SLIP Enjoy your vacation in this well- appointed Bayfront 2 bedroom, 2 bath condo with stunning views of Shelter Island and Greenport Harbor. Amenities include a heated waterfront pool, tennis & pickle ball court, 200 Ft of private sandy bay beach, and your own boat slip in the private marina. Located just a short distance to shops and restaurants in Historic Greenport Village, ferry to Shelter Island for fun day trips and the Hampton Jitney or the LIRR train offer easy access to and from NYC. Everything you need is right here. June 2025 $7000, Sept 2025 $6k , off season 2025 $4k monthly or year round $4500 per month. Greenport rental permit #24-072, Additional information: Appearance:Diamond, ExterioFeatures:Tennis
8 Oyster Point, Greenport, NY, 11944
ML# :805284 Lower Priced 2nd Floor Office Space with Good Natural Light. Larger Main Room, One Smaller Room, One Small Room with Sink, Large 1/2 Bath with Storage. Dedicated Parking Area.
74365 Main Rd, Greenport, NY, 11944
ML# :3587738 Views that never end! Welcome to your picturesque beachfront retreat along the Long Island Sound, where breathtaking water views and private beach access create a serene escape. Enjoy year-round sunsets that will take your breath away. This charming home features a fantastic layout with sun-soaked, high ceilings in the great room, seamlessly connecting the eat-in kitchen, living room, and dining area. The large elevated waterside deck offers easy access, perfect for entertaining or simply soaking in the beauty of your surroundings. The main level accommodates two spacious bedrooms and a full bathroom, while the second level is dedicated entirely to a luxurious primary bedroom complete with an ensuite bathroom and a private waterside balcony-ideal for enjoying quiet moments overlooking the water. Don’t miss this incredible opportunity to own your slice of heaven on the North Fork!
58425 Route 48, Greenport, NY, 11944