Luxury homes for sale & real estate in Shelter Island, NY

Luxury Home for sale in Shelter Island, NY:

Presenting a rare waterfront property in Greenport, for the serious boater. This remarkable home features over 150 feet of waterfront on protected Stirling Harbor, offering the deep water dock space you've been waiting for. The luxury floating dock can easily accommodate oversized vessels, making it ideal for large yachts. Less than 3 years old, it has both 85 feet and 30 feet deep-water sides and is fully serviced with 200 amps of power and internet. Plenty of space for multiple boats, kayaks and friends to pull up waterside. Stirling Harbor offers big-boat access with an 8 foot maintained channel and calm water protection. Also perfect for quick runs to Gardiners Bay and Shelter Island. T

Luxury Home for sale in Shelter Island, NY:

Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering true farmstead character. A large, established two thirds of an acre vegetable garden and an active farm stand highlight the property’s agricultural potential, while the watering hole rises and falls with the rains. Whether you choose to reimagine, repurpose, or preserve this unique homestead

Luxury Home for sale in Shelter Island, NY:

I am proud to bring 605 Gus Drive in East Marion to the market. A custom-built, classic Hamptons style home, nestled on a shy acre at the end of a serene cul de sac. This enchanting property, completed in 2022, offers an exquisite blend of elegance, comfort, and luxury, wrapped in an abundance of natural light. Enter through the front door into a grand foyer boasting elegant 20-foot ceilings. The rest of the groundfloor features 10-foot ceilings, creating an airy, spacious atmosphere throughout the sprawling 3400sq ft of living space(excluding the basement). Oak hardwood floors add a touch of warmth and sophistication to each room and add to the sense of grandeur throughout. The home compri

Luxury Home 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

Luxury Home 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.

Luxury Home 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