MLS Listings for Sale in Shelter Island, NY

MLS Listings for Sale in Shelter Island, NY

Greenport Colonial Close To Village. This inviting Greenport Colonial offers 4 bedrooms and 3 full baths, blending comfort with a prime location. Set on a spacious lot, the home features a welcoming front yard, a fenced backyard with newly refinished hardwood floors, and a new deck-ideal for summer gatherings. Conveniently located close to Greenport Village, you’ll enjoy easy access to shops, restaurants, public transportation, golf, beaches, vineyards, breweries, the North Ferry, and local schools. Whether as a year-round residence or a seasonal getaway, this property provides the perfect balance of lifestyle, location, and leisure in the heart of the North Fork.

MLS Listings for Sale in Shelter Island, NY

Wake up to breathtaking panoramic views of Peconic Bay from your own private waterfront retreat! With 160 feet of shoreline and a 6'x20' dock, this property is a dream for boaters, beach lovers, and anyone craving coastal serenity. Inside, there’s room for everyone with 5 bedrooms, 2 full baths, and a sunlit loft. The wraparound deck invites you to savor spectacular sunrises and sunsets, entertain guests, or simply unwind with the soothing sea breeze. Located in the beautiful Bayview section of Southold, you're just moments from Cedar Beach, and surrounded by the best of the North Fork—award-winning vineyards, charming farmstands, and top-rated restaurants. This property won&rsq

MLS Listings for Sale in Shelter Island, NY

Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Additional Bedrooms and Hall Bath on Second Floor. Finished Lower-Level Family Room offers TV/Sitting Area and Many Storage Closets. Fully Fenced Large Back Yard. Additional Separate Fencing around Inground Heated Saltwater Pool with Easy Automatic Solar Cover and a Pool House. Large Stone Patio for BBQing, Dining and Lounging and Lots

MLS Listings for Sale in Shelter Island, NY

Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen, and entertainment nook, it’s made for barefoot mornings and breezy afternoons with friends. Step outside to a spacious wraparound deck and 130 feet of pristine waterfront — perfect for soaking in the sun, launching a kayak, or simply taking in the view. Secluded yet steps to the pr

MLS Listings for Sale in Shelter Island, NY

Charming Village Colonial in the Heart of Greenport! Nestled on one of Greenport’s most sought-after streets, this beautifully maintained Colonial blends historic charm with modern comfort. Featuring approximately 1,800 sq ft of living space, this home offers 5 bedrooms, 2 full baths, and inviting living areas filled with natural light. The updated kitchen boasts stainless-steel appliances, stone countertops, and custom cabinetry perfect for entertaining or everyday living. Enjoy a seamless flow from the dining area to the cozy living room, complete with original details and hardwood floors throughout. The home also includes a full basement, private driveway, and a detached garage for

MLS Listings for Sale in Shelter Island, NY

Waterfront! Experience the luxury of North Fork living in this bright and airy coastal condo. Located in the coveted Cleaves Point Development known for it's ideal location, picturesque views, and incredible amenities, this 2 bedroom 2.5 bath unit also includes a waterside deck, second floor balcony, full basement, attic and garage! The first floor features a seamless open floor plan including a dining area with glass sliders to the front balcony, kitchen with large center island and breakfast bar, sundrenched living area with sliders to the rear deck, and a convenient powder room. The second floor boasts two bedrooms, two full baths and a balcony with panoramic views off of the primary bed