Shelter Island Homes with Farmhouse Style

Welcome to Shelter Island, New York—a serene gem nestled between the North and South Forks of Long Island. This picturesque community, part of Suffolk County, is renowned for its stunning natural beauty, tranquil beaches, and vibrant local culture. With a population of just over 2,000 residents, Shelter Island offers a unique blend of small-town charm and rich history, making it an ideal haven for those seeking a peaceful retreat from the hustle and bustle of city life.

One of the most enchanting aspects of Shelter Island is its diverse architectural landscape, particularly the charming farmhouse-style homes that dot the island. These residences exude warmth and character, often featuring classic elements such as wide porches, gabled roofs, and expansive gardens. Imagine sipping your morning coffee on a sun-drenched porch, surrounded by lush greenery and the soothing sounds of nature. Farmhouse-style homes here are not just places to live; they embody a lifestyle of simplicity and connection to the land.

Beyond the homes, Shelter Island boasts a plethora of outdoor activities, from sailing and kayaking to hiking along scenic trails. The island’s commitment to preserving its natural beauty is evident in its parks and nature reserves, inviting residents to explore and enjoy the great outdoors.

Whether you’re looking for a year-round residence or a seasonal escape, Shelter Island offers a unique opportunity to embrace a tranquil lifestyle in a stunning farmhouse-style home. Experience the magic of island living, where every day feels like a vacation. Come discover your dream home on Shelter Island!

Newest Shelter Island Homes with Farmhouse Style

$3,625,000

5 Beds ⋅ 5 Baths ⋅ 1012419 MLS

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

43 Gardiners Bay Drive, Shelter Island

$4,800,000

5 Beds ⋅ 4 Baths ⋅ 1007669 MLS

Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island shingled beach house sits on a level acre along one of the Island's most coveted stretches of waterfront -190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy. The expansive side lawn is often mistaken for a separate lot and offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow. A chance to own a piece of Shelter Island's story.

90 Peconic Avenue, Shelter Island

$2,950,000

5 Beds ⋅ 5 Baths ⋅ 977439 MLS

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

12 Terry Dr., Shelter Island

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.