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$3,250,000
3 Beds ⋅ 2 Baths ⋅ 1038472 MLS
There are houses with water views, and then there are houses where the water is the whole point. Located in a waterfront beach community with tennis and pickleball, 380 The Strand delivers the rare North Fork combination of waterfront, an elegant renovation, community amenities, and a setting that feels quietly removed from the world-while still being exactly where you want to be. Picture perfect with the kind of wide-open sunset views that make dinner plans feel beside the point. Lovingly reimagined and offered turnkey, it has the ease of a summer house with the finish and comfort to make it very hard to leave in September. The interiors are fresh, warm, and thoughtfully done-nothing fussy, nothing to "fix". Just arrive, unpack, and settle into the rhythm of the North Fork. A garage adds welcome practicality, while the property offers room for a pool should one feel inclined to make a very good thing even better.

380 The Strand, East Marion
$799,000
2 Beds ⋅ 2 Baths ⋅ 1036090 MLS
Enjoy Exceptional Water Views from this Second-Floor, 2-Bedroom, 2-Bath Condominium Featuring a Spacious Storage Loft and Private Deck Overlooking the Waterside Lawn and Bay. Cleaves Point Condominium Is Beautifully Situated on 13 Waterfront Acres at the End of Shipyard Lane in East Marion. Community Amenities Include a Private Bay Beach, Marina with Docking, Swimming Pool, Clubhouse with Gym, Tennis, Pickleball, Basketball, Community Garden, and More. Conveniently Located Near Island’s End Golf, Greenport Village, and All That the North Fork Has to Offer. Low Taxes Further Enhance This Outstanding Opportunity. Estate Sale. Sold “As Is”.

2820 Shipyard Lane Unit #1B2, East Marion
$1,499,000
3 Beds ⋅ 2 Baths ⋅ 1031857 MLS
Experience waterfront living at its finest, in this exceptional cottage located directly on the Bay. This turn-key, one of a kind property, offers gorgeous water views and open concept living. The dramatic vaulted ceilings with exposed beams, create a stunning focal point, adding warmth, texture, and character throughout the living space. Step outside to your own private beach; perfect for swimming, kayaking, paddle boarding, boating, entertaining, or simply relaxing with your feet in the sand. The panoramic views create an unmatched open-bay lifestyle. Wake up each morning to the soothing sounds of the bay and breathtaking sunrises over the water, just steps from your door. This 3 bed 1.5 bath is waiting for you. Located in peaceful East Marion, this home has close proximity to the Jitney, LIRR, amazing restaurants, and the best vineyards the North Fork has to offer. Simply arrive, unwind, and enjoy the waterfront lifestyle you've been dreaming of.

80 Rabbit Lane, East Marion
$795,000
1026672 MLS
Life's better on the sound! This sound-front lot boasts 50’ of waterfront and approved plans for a 3-bedroom, 2-bath home. Imagine mornings on the porch, afternoons on the water, and evenings with a front-row seat to the most spectacular sunsets around. Whether you're building your forever home, a weekend retreat, or an investment property, this lot is ready when you are and offers the best of North Fork living—just minutes from beautiful beaches, award-winning vineyards, marinas, renowned restaurants, farm stands, boutique shopping.

55915 County Road 48, Greenport
$1,899,999
1017889 MLS
Very near the eastern tip of Long Island’s renowned North Fork, this exceptional 1.37-acre beachfront property presents one of the few remaining opportunities to create a legacy waterfront estate in one of Orient’s most breathtaking coastal settings. Surrounded by panoramic views of Gardiners Bay, Long Island Sound, Plum Island, and the Connecticut shoreline, this remarkable homesite enjoys direct access to a sandy beach and the added distinction of neighboring protected Suffolk County parkland, preserving the natural beauty and open coastal landscape that define this extraordinary location. With approximately 125 feet of private beachfront, the property offers an ideal setting for relaxed coastal living and entertaining. The grounds provide ample space for hosting weekend guests, extended family, or friends escaping the city for beach days, outdoor dining, and slow, restorative mornings by the water. There is also the potential for a waterside pool (permits required), creating the opportunity to design a true resort-style coastal retreat. Wake to spectacular sunrises over Long Island Sound and embrace the quintessential North Fork lifestyle. Spend your days boating, kayaking, paddleboarding, fishing, swimming, beachcombing, or exploring the scenic trails and shoreline of nearby Orient Point County Park. Walk along the beach to take in views of the iconic Orient Point Lighthouse, affectionately known as the “Coffee Pot,” or take the nearby Cross Sound Ferry to New London for a day trip before returning home to the peace and privacy of your waterfront escape. Just minutes away, enjoy the charm of Orient Village, award-winning North Fork vineyards, local farm stands, marinas, and the iconic Duryea’s, where waterfront lunches and unforgettable sunset dinners are part of everyday life. For buyers seeking a more grounded way of living without sacrificing style, comfort, or design, this property offers a rare balance of sophistication, privacy, and direct beachfront access. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life. For city-area buyers ready to trade noise for salt air, open sky, and space to truly exhale, 1890 Lands End Road offers a rare North Fork escape that feels both elevated and effortlessly livable, where cinematic water views, natural beauty, and true coastal privacy come together in one extraordinary offering.

1890 Lands End Road, Orient Point
$2,100,000
1019090 MLS
Build your North Fork Sanctuary on the Sound. This is your opportunity to bypass years of time in the application process. Trustees approval already in place allowing a magnificent 2 story Custom Built home with expansive decks and outdoor spaces and a waterside pool overlooking the Sound. A low bluff with just enough elevation and natural steps to the beach located in a cove allows protection and privacy. Just imagine yourself enjoying the quiet days taking in this spectacular view in the home you have always envisioned escaping to on the North Fork. Floor Plans and Site plan available. Contact Agent

75 Pettys Drive, Orient
$999,000
2 Beds ⋅ 1 Baths ⋅ 1017744 MLS
The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming right out your back door. Surrounded by the gorgeous Southold beaches, over 40 wineries, and local farms, the North Fork has it all. Make it a vacation or year-round home, this is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, Southold
$5,695,000
4 Beds ⋅ 5 Baths ⋅ 1012436 MLS
Introducing a stunning waterfront estate on the Long Island Sound, now available for the first time from its original owners. This coastal gem, located in the North Fork, is situated in one of the most sought-after and picturesque areas on the East End. Nestled on nearly 2 acres, this 4,500 sq. ft. residence offers exceptional views and over 200 feet of private waterfront. The spacious open floor plan includes a junior primary ensuite on the first floor, featuring a separate entrance, a wrap-around covered porch, and direct access to the backyard. The gourmet kitchen is designed to capture breathtaking coastal views, boasting custom cabinetry, high-end appliances, beautiful granite countertops, and a spacious island with seating. Al fresco dining is made easy through the breezeway, which leads to the inviting patio and outdoor decks. The living room and dining room, enhanced by a central fireplace, are filled with natural light and feature beautiful wood floors. Tucked behind the fireplace and accessed through sliding barn doors, the home office offers water views and separate access to the yard. Upstairs, the primary bedroom features a balcony and an ensuite bathroom, showcasing stunning views. Additional bedrooms with balconies, a full bathroom, and a bonus space ensure privacy and comfort for guests. An oversized lounge, also with a waterside balcony and fireplace, connects to the kitchen below via a private staircase, creating an ideal space for a quiet retreat. The spacious art studio, built as part of the expansion, has cork flooring and a wall of windows overlooking the outdoor entertaining space, which includes a fully equipped custom kitchen, dining area, stunning pool, and spa amenities. The yard's mature landscaping and expansive lawn create a welcoming atmosphere for gatherings, with curated spaces for relaxation, including Adirondack chairs nestled along the coastline to enjoy the breathtaking sunsets. Additional amenities include an attached garage, greenhouse, a full unfinished basement with side yard access, and a generator. This property is conveniently located near Greenport Village, wineries, farms, and the bucolic landscape that exemplifies the essence of the North Fork region.

160 Sound Drive, Greenport
$4,250,000
4 Beds ⋅ 5 Baths ⋅ 1007919 MLS
Orient, North Fork - For buyers ready to trade city noise for salt air, open sky, and space to truly exhale, 1640 Grand View Drive in Orient offers the kind of North Fork escape that feels both elevated and completely livable. Set above the shoreline with sweeping, cinematic views over Long Island Sound, this Nantucket-inspired coastal estate combines privacy, scale, craftsmanship, and direct waterfront beauty in one rare offering. With approximately 130 feet of private beach and more than 5,000 square feet of upscale, finely crafted living space, the home is designed around what city life often lacks: light, quiet, room to gather, room to work, and a constant connection to nature. From nearly every living area, the setting frames wide-open views of water, sky, and shoreline, creating an everyday backdrop that feels more like a retreat than a residence. A spacious covered porch entry opens to a gracious foyer and sets the tone for the home’s relaxed coastal character. The dramatic living room, with soaring vaulted ceilings, clerestory windows, and expansive Long Island Sound views, is made for both slow weekends and effortless entertaining. It is the kind of room that can host a holiday dinner, a laid-back summer gathering, or a quiet night in with multiple fireplaces, a record playing, and the water just beyond the glass. The large dining room offers an elegant setting for dinners with friends and family, while the immaculate kitchen with breakfast area overlooks the lush landscape of this private coastal retreat. The open-plan family room, complete with a gas fireplace, flows naturally to the waterside terrace, blurring the line between indoors and out. Morning coffee, golden-hour cocktails, long summer lunches, and late-night conversations all find their place here, with the Sound as the view. The main level includes a thoughtfully designed owner’s suite with fireplace, sunroom/sitting room, and serene private spaces that make the most of the home’s waterfront orientation. A dedicated home office with private en suite bath adds the flexibility modern buyers want, whether used as a true work-from-home setup, creative studio, guest suite, or potentially a fifth bedroom. Upstairs, the home continues to offer room for everyone and everything: a large sitting room, billiard/family room, sewing or craft room, junior owner’s suite with full bath, and two additional bedrooms connected by a Jack-and-Jill bath. The layout is ideal for hosting weekend guests, extended family, or friends escaping the city or a hectic life for beach days, dinners outside, and slower mornings. Immaculate and exceptionally well-maintained, the estate includes a wine cellar, full-house generator, outdoor shower, and many quality details throughout. The grounds also offer room for a waterside pool (permits required), adding the possibility of creating a full resort-style experience at home. For buyers looking for a more grounded way to live without sacrificing style, comfort, or design, 1640 Grand View Drive offers a rare balance: sophisticated coastal architecture, true privacy, direct beach access, and the natural beauty of the North Fork. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life.

1640 Grandview Drive, Orient
$2,700,000
3 Beds ⋅ 3 Baths ⋅ 995366 MLS
A Rare Opportunity!!! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long Island. The home itself offers a sun-filled living room with a fireplace and dining area, both featuring floor to ceiling windows which show off the magnificent seascape. The home also hosts an eat-in-kitchen, 3 bedrooms, 3 baths, a large basement, an oversized 2 car garage, and a large deck to enjoy the breathtaking scenery. If being on the water is for you, you've arrived. Don't miss this one time opportunity.

100 Sound Drive, Greenport
$4,250,000
3 Beds ⋅ 2 Baths ⋅ 923793 MLS
Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside gunite pool and an open-concept interior with modern finishes, designed for effortless indoor-outdoor living and year-round enjoyment. Expansive windows fill the home with natural light while capturing stunning sunsets over the water. Included in the offering is an additional .80-acre unimproved soundfront parcel, providing exceptional flexibility—whether to create a multi-generational compound, expand the existing footprint, or develop a second residence for investment or resale. Ideally located in Greenport near beaches, shops, and acclaimed dining, this rare dual-parcel property delivers a compelling blend of coastal lifestyle, privacy, and long-term value.

56875 Route 48, Greenport
$2,650,000
3 Beds ⋅ 2 Baths ⋅ 975674 MLS
Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor living, ideal for both relaxed summer getaways and comfortable year-round living. Large windows flood the home with natural light while framing the stunning water views throughout. Ideally located in Greenport, just moments from pristine beaches, charming shops, and renowned restaurants, this meticulously maintained property delivers a seamless blend of privacy, convenience, and coastal elegance.

56765 Route 48, Greenport
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 915982 MLS
This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up! Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom adds convenience and flexibility. High ceilings and expansive windows frame the water views, filling the space with natural light. The custom chef’s kitchen features top-of-the-line appliances and flows easily into both formal and informal dining areas. The large living room includes a gas fireplace, game area, and a striking marine-lacquered wet bar complete with fridge/freezer adjacent to both pool and living areas. An additional den with water views offers a quiet retreat or extra space for guests. Outdoors, cedar fencing encloses a private backyard with a heated saltwater pool, areas for al fresco dining, and space to relax. Upstairs features two guest bedrooms sharing a well-appointed designer bath, tub shower combo. The primary suite has stunning water views, cathedral-ceiling, a separate sitting room/office, spacious dressing room, and a spa-like bath with soaking tub, large shower, and separate water closet with bidet. Stone steps lead through beach grass to a private dock—perfect for boating, kayaking, or paddle boarding. Located a few blocks outside Greenport village, yet tucked away from the crowds, and near one of the North Fork’s best bay beaches, this home offers the ideal balance of serenity and convenience. Also available furnished.

980 Manhanset Avenue, Greenport

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.