Greenport New York homes for sale starting at Fifty Thousand Dollars

$3,696,999 - Greenport, NY

250 Osprey Nest Road Greenport, NY - You Have to See It in Person, This Home Feels Even More Incredible Than the Photos Show! People always say, “Wow, I knew it was going to be beautiful, but I didn’t expect it to feel like this!” There’s something about stepping inside that just clicks, the way the light moves through the space, the seamless indoor-outdoor flow, and the effortless luxury in every detail. If you think the photos are stunning, wait until you walk through the door. 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 the tranquil Islands End public golf course, the ever-popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. The neighborhood beach and park offer paddleboard and kayak stations along the marina, but if you’re a boater, you’re in for a treat—private community boat slips give you direct access to the water. From here, it’s just a few nautical miles to Orient Point for world-class fishing or a short ride around the jetty to Greenport Village Harbor, where you can dock for dinner, stroll the waterfront, or explore the vibrant local scene. A Smart Home That Works for You This isn’t just a home—it’s an experience. Designed for both comfort and convenience, the state-of-the-art smart home system gives you remote access to: X Lighting and ambiance control X Heating and air conditioning settings X Whole-home indoor and outdoor audio X TVs in the second-floor lounge, main living areas, and a private basement media room Whether you’re arriving for the weekend or living here full-time, everything is dialed in and ready before you even step inside. Space, Style & Effortless Comfort The expansive floor plan offers not one, but two luxurious owner’s suites—one on the main level for ease of access and another on the second floor, offering a private retreat with elevated views. Two additional guest suites with en-suite baths provide space for friends and family to stay in complete comfort. The sleek, modern design is all about indoor-outdoor living, with oversized sliders that open onto a stunning backyard oasis. Your Private Resort Awaits Step outside, and the magic continues. The elegant pool with a waterfall feature and LED evening lighting sets the stage for unforgettable summer nights. An optional outdoor kitchen, spacious dining area, and cozy fireplace lounge create the perfect setting for entertaining—or simply unwinding after a day on the water. Every inch of this home has been thoughtfully designed across three levels, blending top-tier craftsmanship, effortless functionality, and modern elegance. This is more than just a house—it’s a lifestyle. A rare opportunity to own a slice of resort-like paradise on the North Fork. You have to see it to believe it.

$2,250,000 - Greenport, NY

3200 Bay Shore Road Greenport, NY - Ideally located just minutes from the heart of historic Greenport, this beautifully crafted home offers the perfect blend of coastal elegance and modern comfort. Enjoy direct access to the serene shores of Pipes Cove Beach, where tranquil waters and scenic views invite daily relaxation. Entertain and impress your guests from the bricked patio, and heated saltwater pool. Professional, lush landscaped grounds and local produce from the farm around the road completes the Farm to Table setting! Experience the perfect blend of comfort and classic charm in this stunning 2-year-old farmhouse with expansive water views from multiple rooms. This beauty is located in the coveted Peconic Bay Estates. Meticulously designed and ready for immediate enjoyment, custom details, 4-bedroom, 3.5-bathroom home offers spacious, light-filled living crafted for both relaxation and sophistication. A bright and airy home office offers sweeping views of Greenport’s waterways truly an inspiring place to work or create. Whether you’re strolling the quaint streets of Greenport or enjoying the natural beauty right outside your door, this property offers a lifestyle rich in charm and convenience.

$2,100,000 - Greenport, NY

151 Bay Avenue Greenport, NY - 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., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

$1,995,000 - Greenport, NY

131 6Th Street Greenport, NY - Experience the best of North Fork coastal living in this beautifully appointed 3-bedroom, 2.5-bath waterfront condo with breathtaking views of Peconic Bay and Shelter Island. Enjoy your morning coffee as the sun rises or set sail from your dock just steps from your door. With spacious, light-filled interiors, two fireplaces and seamless indoor-outdoor flow, this home is designed for effortless living and entertaining by the sea. A rare offering in a coveted location-just a few minutes from all that Greenport has to offer; boating, shopping, dining, tasting rooms, art and more!

$1,695,000 - Greenport, NY

2515 Sound Drive Greenport, NY - 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

$1,650,000 - Greenport, NY

308 Wiggins Street Greenport, NY - Incredible investment opportunity to own #1 grossing LEGAL short term Airbnb in Greenport Village. Legally permitted - $220k annually. FULLY TURNKEY from furnishings, bedding / linens, towels, to all kitchen ware, even the artwork Maintenance team including house cleaner, pool care and landscaper are at your disposal. 2 minute walk into town - best location in Greenport, across from LIRR train and Hampton Jitney. Must honor all current Airbnb and VRBO bookings. MAIN HOUSE GROUND LEVEL: Living room with wood burning fireplace, pull out queen sofa, additional 2 person sofa. Captains chair, TV. Full kitchen with stainless steel appliances and chef inspired cookware 4 bar stools Full bathroom with walk-in shower Dining table for 6 Washing machine / dryer 2 air-conditioning units UPSTAIRS: 3 bedrooms - King, Queen and Full bed - all with dressers TV's and window air-conditioning units Full bathroom - double vanity, tub / shower combo BASEMENT APARTMENT / MEDIA ROOM with internal stairway plus external private access. Queen bed pull-out queen sofa Media center with 65 inch flatscreen TV office / work station -mango wood mando wood large coffee table with extended hight dining table dining nook with storage seating kitchen with full dishwasher, 3 x mini fridges, chest freezer, over-oven microwave/convection oven combo Full bathroom - double vanity, deep jacuzzi tub / shower combo Additional full size washer/dryer Dresser and built in closet OUTDOORS heated pool with brand new (April 2022) vinyl liner inflatable jacuzzi 3 brand new wicker loungers with side tables lower patio furniture with gas fireplace Upper deck: dining table for 6 with LED light umbrella additional 2 seats with side table large stainless steel gas grill 2 car driveway 14 ft long storage shed with everything you need to keep the yard looking great Gorgeous landscaping with knock out roses, lavender, hydrangea, peonies, private yard 16 ft tall hedges and more.

$1,495,000 - Greenport, NY

550 Madison Avenue Greenport, NY - Nestled in a quiet corner of Greenport Village, this rare new construction home offers both a peaceful setting and easy access to everything the Village has to offer. Inside, the main floor features open-concept living with large windows and high ceilings, spacious kitchen, separate living and dining areas, and powder room. Upstairs are three bedrooms and two full baths, including a generous primary en-suite bathroom. Outside, you’ll discover your own private oasis: a large yard, a heated saltwater plunge pool, and a level of privacy that’s nearly impossible to find in this location. Ready to add your finishing touches and move in just in time to make the most of Summer 2025!

$1,475,000 - Greenport, NY

130 Tasker Lane Greenport, NY - 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

$1,295,000 - Greenport, NY

795 Westwood Lane Greenport, NY - Elegant & Turnkey in Eastern Shores. This Mid-century Ranch has been Lovingly Renovated (in 2024) and features an Open Plan, Gourmet Kitchen Vaulted Ceilings and Gas Fireplace. Primary Bedroom has Ensuite; 2 Generous Bedrooms w/Bath. Double Sliders in Living Room to Private, Landscaped Backyard w/ Outdoor Kitchen, Heated Pool & Expansive Patio. Deeded Sandy, Sound Beach.

$1,249,000 - Greenport, NY

529 2Nd Street Greenport, NY - This Beautifully Updated 3 Bedroom/1.5 Bath Blends 19th-century Charm with Modern Comfort. The Picturesque Facade Welcomes You Into a Residence that Exudes Timeless Elegance, Thoughtfully Renovated to Preserve its Historical Character While Offering Contemporary Amenities. The Tranquil Yard is a True Oasis, featuring Mature Trees and a Array of Vibrant Plantings. From Rhododendrons and Dogwoods to Blossoming Crabapples and Coral Bark Maples, the Garden and Deck Provide the Perfect Setting for Both Lively Outdoor Gatherings and Peaceful Moments of Reflection. There’s Also Space to Add a Pool, Further Enhancing the Outdoor Living Experience. A Good-Sized Barn (Approx 25' x 15') Offers Additional Opportunity. Ideally Located, This Property is Just Moments Away from The Greenport Library, Great Shops and Acclaimed Restaurants of Greenport Village, Providing Easy Access to Everything You Need While Maintaining a Private and Serene Atmosphere.

Greenport, New York listings for sale

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