Shelter Island Heights Homes for Sale

Shelter Island Heights Homes for Sale

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Shelter Island Heights and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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Newest Shelter Island Heights Homes for Sale

2 Bayview Avenue, Shelter Island Heights
$3,895,000
4 Beds ⋅ 7 Baths ⋅ 1059229 MLS
Welcome to 2 Bayview Ave, a stunning modern home nestled in the serene, walkable streets of Shelter Island Heights, NY. This corner lot property boasts an expansive acre of bucolic land, offering a tranquil escape. The exterior of the home features large front and back porches with ample overhangs for three season comfort. Mahogany decking, porcelain tiles, integrated speakers and overhead fans enhance the enjoyment of picturesque surroundings. The raised backyard is a very private sanctuary of its own with a 16 x 40 gunite pool, a cozy cabana and lush greenery, creating an oasis for relaxation or entertaining. Step inside to a spacious open floor plan accentuated by 10-foot ceilings and a stunning 15ft x 20ft custom window wall that bathes the home in natural southern light. Wide-plank light oak flooring and a cohesive palette of contrasting trim elements evoke a Nordic design language throughout. The custom kitchen is a chef's dream, complete with an oversized quartz island, copious storage, a Thermador appliance suite, and a convenient walk-in pantry. The home is designed for comfortable everyday living and effortless entertaining. Down a windowed hall and separated from the entertaining areas of the home, the primary suite on the main level is a haven of comfort, featuring a large walk-in closet and a luxurious bathroom with double sinks on a floating vanity, a private toilet room and multi-fixture wet room. The main level also houses a convenient laundry room, a powder room, extra closets and a versatile bonus space with its own rear-patio entrance and an attached full bathroom. Upstairs, a cozy, windowed loft space overlooks the main living area. A bright hall joins three additional en-suite bedrooms, including a junior primary suite. Each bath boasts fine fixtures and marble work. The finished lower level provides valuable additional space for recreation, a home gym, media room or overflowing living with a full bathroom and walk-out level access to a private covered patio offers endless potential for customization. The property also includes a 3-car garage – a true rarity in Shelter Island Heights – elegantly situated below the sightlines of the home’s main living areas, thus preserving views of the beautifully landscaped surroundings. A secondary driveway that serves the garage features custom board-formed retaining walls, exquisite plantings and warm landscape lighting that add to the property's striking visual impression. 2 Bayview Ave. is more than just a home; it's a lifestyle. It's a place where modern luxury meets the tranquility of nature.

2 Bayview Avenue, Shelter Island Heights

11 Prospect Avenue, Shelter Island Heights
$2,200,000
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.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.