Shelter Island Heights Real Estate

Nestled in the heart of Suffolk County, New York, Shelter Island Heights is a picturesque gem that offers a unique blend of tranquility and charm. This quaint hamlet, perched on the eastern end of Long Island, is renowned for its stunning waterfront views, lush landscapes, and a tight-knit community that welcomes newcomers with open arms.

One of the standout features of Shelter Island Heights is its serene atmosphere, making it an ideal retreat for those seeking a peaceful escape from the hustle and bustle of city life. The area boasts beautiful beaches, scenic parks, and a network of walking and biking trails that allow residents to immerse themselves in nature. The iconic Shelter Island Heights Historic District showcases stunning Victorian architecture, adding to the area’s charm and historical significance.

The vibrant local culture is highlighted by a selection of charming boutiques, artisanal shops, and delightful eateries that cater to a variety of tastes. Residents and visitors alike enjoy seasonal events, art galleries, and farmer’s markets that foster a sense of community and connection.

For those who appreciate outdoor activities, Shelter Island Heights offers boating, kayaking, and fishing opportunities, as well as access to some of the most beautiful parks and nature reserves in the region. With its rich history, picturesque landscapes, and a strong sense of community, Shelter Island Heights is more than just a location; it’s a lifestyle choice that embodies the essence of coastal living in New York. Whether you’re looking for a permanent residence or a seasonal getaway, this enchanting hamlet promises a life filled with peace, beauty, and endless possibilities.

Newest Listings in Shelter Island Heights

$2,995,000

3 Beds ⋅ 3 Baths ⋅ 1047801 MLS

Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for enjoying the island setting. The home features three bedrooms, 2.5 baths, a chef’s kitchen, formal dining room, living room, parlor, office, full basement, and detached one-car garage—providing flexible space for everyday living, entertaining, work, or guests. Landscaped outdoor areas create a peaceful backdrop for dining, gardening, recreation, or quiet relaxation. Conveniently located near Bridge Street, local shops, restaurants, Shelter Island Yacht Club, and other Heights destinations, the home also includes access to Heights Association parks and the Beach Club, with nearby clay tennis courts. A rare opportunity to enjoy historic character, modern comfort, water views, and the sought-after Shelter Island Heights lifestyle.

13 Spring Garden Avenue, Shelter Island Heights

$1,999,999

6 Beds ⋅ 6 Baths ⋅ 1045616 MLS

Welcome to 4 Bayview Avenue, a remarkable residence nestled in the historic heart of Shelter Island Heights. This expansive property, designed with the art of entertaining in mind, offers a generous six bedrooms and five and a half bathrooms, providing an abundance of space for comfortable living. Upon entering, you'll be welcomed by an array of inviting sitting areas spread throughout the main house, each offering a unique setting for relaxation or socializing. The fully finished lower level, complete with direct access to the pool and backyard, adds a layer of versatility to the living space. This home is equipped with a variety of desirable features such as central air, a cozy fireplace, and a dedicated office space, ensuring your every comfort and convenience is met. The private guest quarters serve as a separate haven for visitors, enhancing the overall accommodation. The outdoor space is a haven of peace and privacy, with beautifully landscaped grounds and mature trees. The newly installed expansive mahogany decks, adorning both the main house and guest house, offer the perfect backdrop for outdoor gatherings and soaking in the surrounding natural beauty. The property also invites you to partake in community amenities such as a beach club and tennis, allowing you to fully embrace the joys of coastal living. A two-car garage with radiant heat flooring adds to the property's convenience, while the heated gunite pool and outdoor shower offer additional luxuries. With a vast area of approximately 6,098 square feet, this home is designed to cater to a variety of lifestyle needs. This exceptional property in Shelter Island Heights is waiting for you to make it your own. Don't miss this opportunity. Schedule a private viewing.

4 Bayview Avenue, Shelter Island Heights

$2,595,000

4 Beds ⋅ 3 Baths ⋅ 1022345 MLS

Shelter Island Heights Icon Gracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor its original character while seamlessly incorporating today's modern comforts. Rich in architectural charm and classic detail, the home offers an elegant blend of historic beauty and refined living. A gracious, oversized covered porch welcomes you upon arrival, providing the perfect setting to relax and enjoy the property's elevated position and picturesque water views. Inside, a warm and inviting foyer opens to beautifully proportioned living spaces, where natural light, period details, and a sense of understated sophistication create an atmosphere of effortless elegance. Toward the rear of the home, a formal dining room and well-appointed kitchen serve as the heart of the residence. Expansive windows and French doors bathe the interiors in natural light while creating a seamless connection to the surrounding landscape and outdoor living spaces. The second level is highlighted by a spacious primary suite featuring a generously sized bath, accompanied by two well-appointed guest bedrooms designed for comfort and privacy. The third floor offers a versatile retreat, ideal as a media room, den, home office, or additional gathering space for family and guests. Outside, the beautifully landscaped grounds provide a private sanctuary framed by mature trees and established plantings, creating a tranquil setting for relaxation and entertaining alike. Ideally situated just moments from the coveted Shelter Island Heights Beach Club, tennis courts, golf, marinas, shops, and beloved local restaurants, this exceptional offering presents a rare opportunity to own a meticulously restored home in one of Shelter Island's most desirable and historic neighborhoods.

11 Prospect Avenue, Shelter Island Heights

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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.