luxury real estate for sale Shelter Island Heights, United States

Nestled among the shores of Pipes Cove, this exquisite bayfront home offers the ultimate beach lifestyle, combining relaxation and panoramic views around Conkling Point over to Shelter Island. Every Wednesday evening, chill out on the waterside patio and watch the Shelter Island sailboat races. Have front row seats to the annual 4th of July Shelter Island fireworks display. If you're an early riser, here you'll be captivated by breathtaking sunrises. Launch kayaks, paddle boards, or even a small sailboat from your own beachfront, and explore the waters at your leisure. The home exudes warmth & character, inviting you to unwind and revel in the simple pleasures of life on the Bay. The open floor plan with living, dining, & kitchen are thoughtfully designed to maximize water views and natural light. The primary suite is on the first level with 2 additional bedrooms & a full bathroom. Upstairs has a loft and unfinished space ready to be built out. All of this, only a 3 minute drive to the coveted Greenport Village.

Don't miss out on this Light-filled 3-bedroom, 2-bath custom built modular home, built in 2020. It offers a superior living experience with its solar-powered, Energy Star, and LEED compliant features. Located across the street from Peconic Bay, it boasts peek-a-boo views of the bay with nearby access points to a kayak launch, and tranquil Pipes Cove. This ranch layout includes an upstairs room that can serve as additional living space or an office, providing privacy from the rest of the house with a walk out veranda. Thoughtful gardens outside the living room blur the lines between indoors and outdoors, enhancing the overall ambiance. Residents can relax on the veranda or in the living room while enjoying the scenic views. Additionally, the property features a two-car garage, suitable for parking or storing water sports equipment, and a full, spacious basement that offers ample storage and potential for additional living space. Take advantage of the nearby attractions of the North Fork, including Shelter Island, beaches, farms, vineyards, and restaurants, all while enjoying the tranquility of a small-town atmosphere. Whether you're looking for a peaceful retreat or an active lifestyle surrounded by nature, this home offers the best of both worlds.

Turn-key mixed use offering in the heart of Greenport Village. This space was completely overhauled in 2017 w/ all new HVAC, plumbing and electric. The property is located in the commercial retail district of the village and offers an array of uses, which include and not limited to accessory apartment, gallery, eating and drinking establishment, studio, event space, dry retail, professional office, etc.. The space is currently set up and CO'd as a restaurant and features a large bar, two bathrooms and an area that would be perfect for an open kitchen on the main floor. The second level is a lounge w/ additional half bathroom offering additional seating and views of Greenport shipyard and Greenport Harbor. The lower level consists a prep area, walk-in fridge, ample space for storage and a majority of the mechanicals. This is an investor opportunity or a great space for an end user operator in an ideal location 1 block from the center of the Village

Classic contemporary style New Construction in the heart of Greenport Village. This 2900+ sqft offering features 4 wide white oak hardwood floors throughout w/ inviting Great Room, eat-in Kitchen and Junior Suite bedroom on Main Level. The second floor features an cozy additional den/media room with two generously sized guest bedrooms sharing a full bathroom, laundry, ample storage, a primary ensuite bedroom with walk-in closet and large walk-in shower. In addition to the 1st and 2nd floors is a partially finished basement that is rough plumbed for an additional full bathroom and the possibility of converting into a legal apartment with separate outdoor access already in place or as lower level gym or media room. For those looking for tremendous value and as central Greenport Village location, this is an absolute must see. ADDITIONAL PHOTOS TO FOLLOW

Lovely Ranch in Hay Beach is sited on 1.06 Acres, with an eat-in-kitchen, a formal dining room, a den/family room, 3 bedrooms, one of which is a Master Bedroom suite with a walk-in closet, and 2 additional guest bedrooms with hall bath. This spacious home also features Cathedral/Vaulted/High Ceiling, Hardwood Floors, a Home Office, Pantry, Powder Room, Sky Light, and Storage.

Contemporary Barn Style Home Nestled on 1.47 Acres is a 1.5 Story Contemporary Barn Style home with cedar siding. Upon entering this property, the meandering driveway leads to beautiful flowering gardens, mature trees and a spacious yard. There are wide plank pine floors throughout, the home has an open living plan and detailed hand-hewn timbers. The front of the home opens onto a wonderful southwest facing deck and provides passive solar energy to this property. The second floor is unfinished with 14-foot ceilings and BOH approval for a 4-bedroom home. This property is close to Crescent Beach, restaurants and shops.

Convenient to all at 28 Smith Street. The address was originally owned by the Smith family, and it's newly built, well considered, expanded and very charming with three bedrooms 2 full baths and room for a pool on a centrally located corner lot.

101 Sterling Street, Greenport, NY 11944

Situated on a shy acre, is a beautiful traditional, Hampton's style shingle home. With over 5000 sq. ft. of living space on mostly one level, this home has it all. The grand foyer welcomes you with vaulted ceilings and opens into the living room with wood burning fireplace. The chef's kitchen offers luxury appliances, large island, granite counters, wet bar and breakfast area. Most rooms lead to the rear courtyard, with patio, wood burning fireplace and heated Gunite pool. The primary bedroom en-suite and the separate guest wing with den and fireplace creates an estate like feeling. Enjoy this amazing home and add an additional builders acre that is adjacent to this home. This property is centrally located and minutes to beaches, shops, dining, school and ferries to both the Hamptons and the North Fork.

Lovely 3 bedroom 2.5 bath home in the Hay Beach area of Shelter Island. The kitchen has high-end appliances and granite countertops opening to the living room with a fireplace and dining area, also a den area for watching TV and playing games. Enjoy the inground pool and Bullfrog custom hot tub, and dining patio. The home is sited on .96 partially wooded acres and has a 2-car garage with a circular driveway.

880 Kerwin Boulevard, Greenport, NY 11944

620 Kerwin Boulevard, Greenport, NY 11944

Introducing 165 Angler Rd, a beautifully custom-designed,new construction home that fulfills every buyer's wish list. Positioned just steps from a pristine Bay beach and in close proximity to Greenport Village's vibrant waterfront district, this residence boasts a sophisticated spa-like heated in-ground pool with a stone patio surround and is incredibly well appointed, seamlessly blending traditional details with chic modern elements. With three floors of finished space including a fully finished basement hosting a home office, media room, and full bathroom, this home offers versatile living options. The main level features 9ft ceilings with a light-filled open Great Room, a first-floor bedroom and bathroom, while the third level features two guest bedrooms sharing a full bathroom and a generously sized primary bedroom with a private full bathroom and an oversized walk-in closet. The superb craftsmanship of this home is evident in the custom millwork, built-in shelving, rift and quartered hardwood floors, and upscale finishes. Equipped with dual-fiber-optic cable lines and Cat6 ethernet in all bedrooms and living spaces, this home provides an ideal work from home environment and remote monitoring capabilities for added convenience. The chef's kitchen is designed for culinary enthusiasts, featuring GE Cafe appliances, wall-to-wall stone counters, wine fridge, floating shelves, built-in wine storage, and a large center island, perfect for year-round entertaining. This exceptional Greenport residence offers the perfect blend of sophisticated finishes, modern amenities, and a prime location. Not to mention, you will enjoy world class vineyards, local breweries, hiking trails and many additional beach options between the Great Peconic Bay and LI Sound.

THIS TURNKEY HAS IT ALL Uniquely perched above a magical 1.30+/- acres this 3,000 sf+/- newly renovated waterfront contemporary sits on the revered and sheltered Menantic Creek. 300 feet of water frontage with a private deep-water dock with the capacity for 4 boats that allows for easy access to West Neck Harbor and the Peconic Bay beyond, all within close proximity to the coveted Island Boatyard, rightfully secures this home as a boater's paradise. Extensive decks, a Japanese style rock-terrace, abundant lush gardens, a newly built gunite pool surrounded by white marble, a hot-tub, outdoor shower and sauna are all easily accessible from the home, designed for ultimate indoor-outdoor living. The interior has soaring ceilings and is flooded by natural light from the bank of waterfront windows and sliding glass doors. The kitchen features quartz countertops and stainless steel appliances and adjoins an all year glassed-in pavilion that overlooks the spectacular Menantic Creek vista. All bathrooms have been meticulously renovated, the primary with Carrara marble. There are two bedrooms on the first floor, including a large first floor primary suite with stunning water views and direct access to decking and all that the property affords. There is an additional first floor bedroom with an ensuite bathroom. The second floor consists of another primary suite offering phenomenal panoramic water views plus an additional bedroom and a private office overlooking the every changing landscape, an expansive lawn and the luxurious pool. The finished lower level has a full bath that adds an additional 800+/- square feet of living space. A two car garage and separate garden shed, and the possibility of expansion rounds out this offering . A stellar location near world class restaurants and shopping, a quick drive to the south ferry to North Haven/Sag Harbor, golf, tennis and so much more. 11 Dickerson Drive is the very best of year-round living on Shelter Island.

Waterfront home with floating dock and bulkhead with water views and bay breezes on protected Stirling Harbor with access to Peconic Bay. Featuring covered waterside front porch, great room with gas fireplace, formal dining room, spacious eat-in kitchen, half bath, and laundry on first floor. Master suite with sitting room/office and full bath, and 2 additional bedrooms and full bath on second floor. Attached 2-car garage.

1.48 acre, private, cleared flag lot close to Greenport Village.

Welcome to this stunning Ranch nestled in the serene and sought-after neighborhood of Silver Beach on an impressive .87 acre lot with beach rights. This meticulously maintained residence offers a perfect blend of modern comfort and timeless elegance. Upon entering, you're greeted by an inviting living room accentuated by gleaming hardwood floors. The spacious living area seamlessly connects to the chef-inspired kitchen, complete with sleek stainless steel appliances, granite countertops, and ample cabinetry - an ideal setting for culinary enthusiasts and entertaining guests. Just off the dining area is a sunken enclosed sun room, insulated for all seasons. This tranquil area provides ample natural light and generous space for another living space or dining area. Two of the exterior walls are made up with floor to ceiling windows. Allowing for one to be completely surrounded by nature. Another key highlight of this home is its captivating outdoor space. The private backyard is perfect for relaxation or gatherings, with a well-manicured garden and a charming lounge area - an ideal spot for al fresco dining or enjoying the picturesque views.

Rare offering in high traffic location on the Main Rd in Greenport adjacent to Islands End Golf Course. This long standing restaurant establishment offers a turn-key opportunity with full kitchen, bar, 70+ seat BOH approved seating, dining room, parking and equipment. Along with the commercial usage, this property also offers a 2 bedroom, 1 bathroom guest cottage. This location can see 40K+ cars pass by on a given summer day, so the road exposure is more than ideal. Whether you an end user looking to occupy the guest cottage while running the restaurant or an investor looking for ideal invenstment opportunities, this property will deliver.

Escape to tranquility in this beautiful contemporary home nestled on Shelter Island. Built in 1993, this 3-bedroom, 3.5-bathroom residence boasts 2,460 square feet of meticulously crafted living space, perfectly positioned to capture breathtaking water views from nearly every room. Upon entry, you're greeted by the inviting ambiance of the great room, featuring a majestic gas fireplace and expansive windows framing panoramic vistas of the tranquil pond. Sliders invite you to step outside onto the deck, where you can savor morning coffee or entertain guests against the backdrop of serene waters. Adjacent to the great room, a screened porch awaits, providing a peaceful retreat for relaxation in the cool breeze. Close Proximity to Wades Beach and less than a mile to South Ferry, just a short distance to the Hamptons.