Shelter Island Homes with Cottage Style

Welcome to Shelter Island, a hidden gem nestled in the heart of Suffolk County, New York. This enchanting island, flanked by the shimmering waters of the Peconic Bay and the Atlantic Ocean, offers a serene escape from the hustle and bustle of everyday life. With its charming small-town atmosphere, lush landscapes, and captivating waterfront views, Shelter Island is a haven for nature lovers and those seeking a peaceful retreat.

As you explore this picturesque community, you'll discover a delightful array of homes, particularly those showcasing the timeless charm of cottage-style architecture. These quaint residences often feature cozy interiors, inviting porches, and beautifully landscaped gardens that exude warmth and character. Imagine sipping your morning coffee on a sun-drenched deck or hosting summer barbecues in your backyard, surrounded by the intoxicating scent of blooming flowers and the gentle rustle of leaves.

Cottage-style homes in Shelter Island embody a unique blend of rustic charm and modern comfort, making them perfect for both year-round living and seasonal getaways. Many properties are just a stone's throw away from pristine beaches, scenic parks, and vibrant local shops, ensuring that every day is an opportunity for adventure and relaxation.

Whether you're drawn to the island's rich history, its breathtaking natural beauty, or the close-knit community spirit, Shelter Island promises a lifestyle that's both enchanting and fulfilling. Come and discover your dream cottage-style home in this idyllic setting, where every moment feels like a vacation. Your perfect piece of paradise awaits!

Newest Shelter Island Homes with Cottage Style

$1,200,000

3 Beds ⋅ 2 Baths ⋅ 1013318 MLS

Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home.

16 Bowditch Road, Shelter Island

$2,700,000

6 Beds ⋅ 3 Baths ⋅ 1005789 MLS

A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages features two bedrooms and one bath, with strong summer rental histories and an undeniable sense of place rooted in the island’s coastal charm. Rich in character and provenance, each residence tells its own story. The Hill Cottage, dating to the 1890s, is a one-of-a-kind former boathouse thoughtfully relocated from a grand Nostrand Avenue estate, with original architectural details preserved throughout. The Red Cottage, originally built in the 1920s as a fisherman’s retreat, has been expanded to include enclosed patios at both the front and rear. The Main House, constructed in the 1940s, has been carefully renovated to enhance modern comfort while maintaining the craftsmanship and warmth of its era. Completing the offering, the adjacent lot at Rock Point Road presents a rare blank canvas, ready for a primary residence and pool, surrounded by three established rental cottages. Whether envisioned as a private multi-generational retreat, a boutique rental compound, or a long-term development investment, this is a truly exceptional opportunity to own a piece of Shelter Island’s history with both immediate income and enduring upside in one of Long Island’s most sought-after enclaves.

2 Prospect Avenue, 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.