Beautifully updated & fully renovated in 2020, Arts & Crafts style home in the heart of Orient Village, one block from Orient Harbor, walking distance to post office, country store & all village amenities. Open concept dining/living room with large wood burning fireplace. Updated gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher, & wine cooler. Enclosed front porch sunroom. Second floor master bedroom with large balcony overlooking the garden with ensuite bath – 2 sinks, free-standing tub & walk-in shower. Two additional bedrooms and full bath with tub and front-loading washer/dryer. Fenced yard, outdoor shower, backyard deck & lower patio for outdoor dining & entertaining. Professionally landscaped with mature trees and flower beds. Detached 1-car garage.

There are homes that look beautiful in photos, and then there are homes that make you understand the scale, privacy, and presence only after you pull through the gates. This is one of those homes. The location makes it even better. You are about 10 minutes to Ponquogue Beach on Dune Road, about 17 minutes to Cooper’s Beach in Southampton, and still close enough to get to Cowfish for brunch on the water. It gives you privacy, scale, and a true Hamptons lifestyle without feeling like the whole world is watching from the hedges.

As you arrive at the end of the cul-de-sac, the setting immediately feels private and established. The double entrance gates are framed by lush landscaping on both sides, and the keypad entry makes it easy for guests to arrive without any fuss. The curving driveway sets the tone beautifully, with mature plantings along the adjoining properties creating year-round privacy. It feels completely discreet, with just the right framed views of the gardens to complement the stately brick exterior and copper details of the home.

Inside, what stood out to me right away was the size of the rooms. The photos are beautiful, but the home feels even larger in person. The entry foyer is impressive, and the formal receiving room has a rich wood inlay detail and a fireplace that anchors the space perfectly. It feels elegant.

The family room is exactly where everyone will naturally gather. This room has a large sectional, built-in bookcases, and a custom TV cabinet that brings in the warmth of real woodwork we aren't seeing anymore. It feels comfortable, substantial, and made for us.

The kitchen and dining areas are just as generous. You could easily host 10 to 12 people without trying too hard. The views out to the bluestone patio make the space feel connected to the outdoors, and the built-in Sub-Zero side-by-side refrigerator and freezer are ready for our weekend dinners, holidays, and time by the pool. The island and breakfast bar keep everyone in the kitchen, but with enough space so no one is in your way while you are actually trying to cook.

Just off the kitchen and garage is a beautifully finished home office with custom woodwork and textured wall panels. Across the hall is a guest or nanny bedroom with a full bathroom, giving us a practical layout for extended stays, staff, or anyone who needs a private first-floor space.

Upstairs, the scale continues. There is a second office with wood bookcases, natural lighting from the exterior access to a Juliet balcony overlooking the front entry. Each bedroom has its own en-suite full bath, which makes the choices easier. The primary suite is especially impressive, with mine and your closets and enough room for an Alaskan king bed, yes, the 9-foot by 9-foot kind. That tells you everything you need to know about the size of the room.

The backyard is where the property really becomes something special. It is completely private, with a bluestone dining patio, a fenced lounge deck by the pool, and a waterfall feature that gives the whole space that quiet resort feeling. There is also the option to purchase the separate rear lot, which the current owners have used to preserve the curated garden aesthetic.

That second lot opens up a very interesting possibility. It could remain as part of the private oasis, or it could offer the opportunity to create a connected compound with a separate home and its own entrance from Fordham Road. Translation: everyone can be close, but not necessarily under the same roof all weekend. We meet at the pool. That is the civilized plan.

Set on 1.16 acres of beautifully landscaped and private grounds, this charming North Fork property offers space, versatility, and serene farm vistas. The main home features 4 bedrooms, 1.5 baths, an eat in kitchen, living room, and sitting area filled with natural light. A remarkable 6 car garage currently houses a Michael Phelps lap pool with hot tub and sauna, creating a unique year round wellness retreat and offering endless possibilities for a contractor, artist, car enthusiast, or home gym. A separate guest house barn with wood burning stove provides additional comfort and flexibility. Solar panels with EV charging keep electric costs extremely low, approximately $17 per month. Central air, oil heat, and public water add convenience. Cutchogues’ Causeway Beach ,Mature landscaping, exceptional privacy, and room for a pool or tennis or pickleball court complete this special offering.

Steeped in the history of Orient, this exceptional Craftsman-style residence occupies a remarkable setting along historic Main Road, once known as King’s Highway, directly across from the entrance to Orient Beach State Park. Originally purchased by a member of the pioneering Latham farming family, the home was thoughtfully expanded in the 1920s with the addition of its signature wide front porch and interior improvements. In 1938, the family donated the land across the street that would become the entrance to today’s Orient Beach State Park, forever connecting this property to one of the North Fork’s most treasured destinations.

Architecturally, the home showcases timeless Craftsman character with distinctive three part windows across the front facade, each crowned with elegant lozenge paned transoms. The welcoming front entrance, framed by classic sidelights, opens to interiors where original woodwork, period doors, and handcrafted details remain beautifully intact. Modern updates to the large country kitchen, bathrooms, natural gas heating, and central air provide today’s comforts while preserving the home’s historic integrity.

The property’s story extends beyond the main residence. A historic building from the famed Orient Point Inn, a resort established in 1672, was relocated to the backyard in the early twentieth century. Once serving as the inn’s men’s rooms and kitchen building, it now anchors the grounds as a fascinating reminder of Orient’s maritime heritage.

Life here is defined by both history and location. Relax on the expansive front porch where seasonal water views, cool coastal breezes, and the distant sound of ferry horns create an unmistakable North Fork atmosphere. The original wood-burning fireplace, gracious front and rear staircases, and oversized country kitchen invite gatherings both large and small.

Protected open space bordering one side of the property, paired with a classic neighboring farmhouse and historic barn on the other, preserves the peaceful character that has defined Orient for generations. Just moments away are Orient Beach State Park, Duryea’s Marina and Restaurant, the Cross Sound Ferry, and Orient Point County Park with its iconic lighthouse. Whether exploring by bicycle, spending the day on the beach, or simply enjoying the quiet rhythm of this waterfront community with some of the best fishing off of Plum Gut, every day feels connected to the rich history and natural beauty that make Orient one of Long Island’s most treasured destinations.

This is more than a historic home. It is an opportunity to become the next steward of a property that has helped shape the story of Orient for generations

Here’s what I love about 2120 Crown Land Lane in Cutchogue.

The first thing that stood out to me was the setting. Across the street, you have this beautiful stretch of woods that will not be built on, and it gives the front porch such a calm, private feeling. Sitting there in the evening, catching the sunset over that side of the neighborhood, you immediately understand why this house feels different.

The approach is also beautifully done. The driveway is finished with Belgian block edging, the walkways to the front and back of the home have landscape lighting, and the evergreens along the property create this polished, private view of the house and backyard. It feels manicured, but not stiff.

Then you get to the backyard, and honestly, this is where the house really shows off. The grilling pavilion is fantastic, but the fire pit area is one of the best conversation spaces I have seen. A radius-cut floating bluestone bench wraps around individual seating areas and a 4-foot fire pit, all set on a bluestone patio and anchored by a stunning magnolia tree. Just beyond that, there is a bocce ball court, the pool area, and another outdoor room that makes the whole backyard feel like a private resort.

What makes it even better is that all of these outdoor spaces have speakers and lighting, so whether it is a quiet night by the fire or a full summer gathering, the atmosphere is already built in.

Inside, the kitchen is exactly what you hope to find. Thermador appliances, a 4-burner gas cooktop with griddle, beverage drawers, wine storage, double ovens, microwave, and this incredible shade of blue on the island and cabinetry that gives the space personality without feeling trendy. It is custom, useful, and beautiful all at once.

The home also has speakers in the kitchen, den, and living room with fireplace, along with Lutron smart home lighting, which makes entertaining feel easy. The bathrooms are beautifully updated with tile selections that feel current, but timeless.

Add in access to amazing sandy beaches in the Cutchogue Park District, the library, school, diner, and easy access to the Hampton Jitney for NYC, and this home starts to make a lot of sense.

It has so many of the features people are looking for in new construction, but without the new construction price tag. That is why I love it.

Nestled in the heart of the North Fork, this beautiful 4-bedroom, 2 1/2-bath Colonial offers the perfect blend of coastal charm and everyday convenience. Ideally situated near golf courses, pristine sandy beach, acclaimed restaurants, wineries, and the vibrant downtown area, this home provides an exceptional North Fork lifestyle.

Inside, you'll find spacious living areas filled with natural light, generously sized bedrooms, central ac upstairs, and a thoughtfully designed layout perfect for both entertaining and comfortable family living.

Step outside to your own private retreat featuring a large patio overlooking a beautifully landscaped backyard. The tranquil koi pond, elegant arbor, and lush gardens create a peaceful setting for outdoor dining, gatherings, or simply relaxing after a day at the beach or golf course.

Whether you're seeking a year-round residence or a seasonal getaway, this charming Colonial offers the best of North Fork living in a highly desirable location.

Wake up to the sound of gentle waves and breathtaking sunrises over Gardiner Bay in this charming four-bedroom, two bath coastal retreat. Nestled in the heart of Orient, this home blends classic North Fork charm with modern comforts. Step inside to find a bright, airy interior with open-concept living spaces, hardwood floors, and windows that capture stunning water views. The spacious kitchen offers ample counter space and flows seamlessly into the dining and living room areas, perfect for entertaining. Outside, enjoy a private porch overlooking the bay and a short stroll to a private sandy beach and Orient’s quaint village. Whether as a year-round residence, weekend escape or investment property, this gem offers the best of the North Fork.

Welcome to 550 Madison Avenue in Greenport, a thoughtfully designed New Construction farmhouse that feels comfortable from the moment you arrive. The covered front porch is more than an architectural detail. There is actually room for a chair and side table, creating the perfect spot for a quiet morning coffee.

Inside, wide 6-inch oak floors connect the bright, open living spaces. The powder room is conveniently located near the front entrance, but it is tucked far enough away from the open living room, dining area, and kitchen to give everyone a little privacy when the house is full.

The custom kitchen design brings together the features buyers keep asking for, including a paneled refrigerator, a full pantry closet, open shelving, generous cabinetry, and a kitchen sink positioned beneath a window overlooking the backyard. Even doing the dishes comes with a view of the established maple trees.

A full glass slider in the dining area fills the back of the home with natural light and creates an easy connection to the outdoor entertaining spaces and grill. The backyard views can also be enjoyed from the living room, making the surrounding landscape feel like part of the interior design.

Upstairs, the primary bedroom features a peaceful en-suite bathroom with distinctive tile flooring and calm, carefully selected finishes. Even the first-floor powder room has beautiful wallpaper, adding personality and making this New Construction home feel intentional rather than predictable.

The fully fenced backyard is surrounded by established maple trees, creating a quiet and private setting that feels like a hidden corner of Greenport. The newly installed stone patio includes an outdoor cushioned conversation area, a separate outdoor dining patio, and a dedicated fire pit for evenings under the trees. There is also room to explore the possibility of adding a pool without making the yard feel crowded.

The location brings the North Fork lifestyle within easy reach. The Greenport LIRR station and Hampton Jitney stop are approximately half a mile away for convenient transportation to New York City. Aldo’s Coffee is about a three-minute bike ride or a ten-minute walk, with Greenport Village shops, restaurants, waterfront destinations, and local beaches all close enough to enjoy without always getting back into the car.

New Construction, a custom kitchen, paneled appliances, wide oak floors, en-suite bathrooms, a fenced backyard, mature trees, outdoor entertaining spaces, and easy access to Greenport Village. This might be the one you have been waiting for. You really need to come see it. In the evening it sparks with fireflies to capture summer vibes in Greenport Village.

Welcome to North Fork living at its finest! This beautifully maintained 3-bedroom 2 1/2-bath home offers the perfect blend of
coastal charm and comfort, ideally located just moments from the golf course and with private beach access. Surrounded by
stunning, professionally landscaped grounds, the property features an inviting deck and spacious patio-perfect for outdoor
entertaining or relaxing in a peaceful setting. Inside you will find a layout designed for both everyday living and weekend
getaways. Whether you're seeking a year-round residence or a serene retreat, this exceptional home captures the best of the
North Fork lifestyle

Discover timeless charm and classic North Fork living in this stately 1910 Grand Dame, gracefully sited in one of Cutchogue’s desirable locations. Featuring four bedrooms and three well-proportioned floors, this distinguished home showcases a gambrel roof and period details that reflect a bygone era.
Ideally situated just moments from the heart of Cutchogue village, you’ll enjoy easy access to local restaurants, shops, the library, and nearby beaches. Golf courses, vineyards, and award-winning wineries are all within minutes, offering the best of North Fork’s coastal lifestyle.
This property backs up to the historic The Old House - 1649 property, one of the original homes on the North Fork, providing both privacy and a sense of place steeped in local history. With generous living space, classic architectural lines, and a location that balances tranquility with convenience, this rare offering is perfect as a full-time residence or cherished weekend retreat.

Come make your mark on a true North Fork classic.

Walking into this place, I actually said “okay…this is exactly what I’ve been hunting for”.
First off, it’s not just a condo, it is a complete waterfront beach resort. They have recently refreshed tennis courts tucked into these tall pine trees, so even when you’re just standing there you feel vacation vibes. Then you turn the corner and there’s the pool scene: plenty of lounge chairs so you can do the sun or shade depending on the tan line status.
The gym is right next to the pool with updated equipment, and it looks out over the pool so I can actually stick to a flexible plan: quick workout, then laps, then back to the pool chair. Or I can skip all of that and go straight to the sandy beach and just wander the shoreline that even has a view toward the lighthouse out by Orient Beach State Park.
Now the best part: this is a second-floor unit, which means nobody is above and that changes the whole ceiling and layout. What I really like is the commanding water view from the kitchen, living room, and deck. The living room has double-height ceilings and a fireplace, so it feels open and airy, not boxed-in—and the water views are unreal as the weather changes. The main bedroom has its own water view and with the high ceiling and the updated bathroom has fresh open feeling.
The kitchen is dialed-in with views of the water—new stainless steel appliances, quartz counters and a breakfast bar that keeps everyone on the living room side.
The deck is set up brilliantly: there’s an extra counter with stools along the living room wall, so you’ve got this indoor-outdoor wine-and-cheese flow that feels effortless. And somehow the deck is built so you don’t really see the neighbors—no idea how but I’m a fan. When the others come out, there’s a second floor den with water views too (because the living room ceiling is so high, it creates this cool extra space).
Islands End Golf Course and the Hellenic are under a mile away, so that’s a two-minute drive. Greenport Village is only about 2.5 miles away for shops, food, and everything that I love to do on the North Fork.
And then it hit me, the Shelter Island ferries are right there. That opens up Shelter Island restaurants, quick trips toward Sag Harbor. If I have to run into the city, the train and Hampton Jitney are right by the ferry terminal too, so it’s genuinely easy to come and go.
This is one of those places that makes sense in every season, summer, fall, winter and the best part is when I lock the door, I am not stressing outdoor maintenance. I can just leave, head south, and actually relax. Then the new clubhouse is across the path by the gas grill patio where I can keep my own, tennis courts offer pickle ball also and the pool and decks have all new tables, chairs and umbrellas. The new gym is one of the best I have seen in the area. This is great space for summer gatherings with the new restrooms and kitchen space. They even have a huge flatscreen tv in the Clubhouse. The floating swim platform is close enough to the sandy beach and Adirondack chairs, I can see this getting lots of use. What an amazing location, feels like a vacation resort on the beach for sure. The boat docks are available so there is time to take the most of fishing by the Gut at Orient Point.

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

Welcome to this well-maintained 3-bedroom, 1-bathroom home located just a half mile from the beach.

Enjoy a sunny, fenced backyard featuring a beautiful bluestone patio—perfect for relaxing, entertaining, or summer barbecues.

This inviting residence has been a cherished family home for years. Additional highlights include a spacious attached two-car garage, single-level living, and low-maintenance ownership with economical operating costs.

Whether you’re looking for a year-round residence, a downsizing opportunity, or a beach-area retreat, this practical and comfortable home offers a relaxed lifestyle in a desirable Wading River location.

Just minutes from beaches, parks, wineries, and all the North Fork and Wading River area have to offer.

Located in the San Remo Community, North of 25A this charming 2 bed 1 bath Cape Cod is nestled in the heart of Kings Park. This home offers the perfect blend of cozy living and charm. Bright and inviting summer room , expansive deck with winter water views for your own private escape for entertaining or relaxing. All utilities along with roof have been upgraded and are 5 years new.

The adjoining rear lot may be one of the most interesting parts of the 10 Emerson Court opportunity.

Right now, it feels like a natural extension of the backyard. It is completely fenced in, surrounded by privacy landscaping, and designed in a way that protects the secluded feeling of the main residence. From the bluestone patio, pool, and garden views at 10 Emerson Court, this rear parcel adds another layer of quiet, green space that makes the whole setting feel even more private.

What makes it especially valuable is that this is a flag lot with access from Fordham Road, giving it its own separate point of entry. That means it can continue to serve as part of the private garden setting for 10 Emerson Court, or it can become something much bigger: a future family compound.

This is the kind of setup people always talk about wanting, but rarely find. Keep the main house as the gathering place, then create a second residence nearby for extended family, guests, adult children, parents, or anyone you love dearly but do not necessarily want making coffee in your kitchen at 6:30 every morning.

Everyone stays connected, but everyone still has their own space. The pool becomes the meeting place. The gardens become the shared view. The two properties can work together while still allowing privacy, flexibility, and breathing room.

The adjoining lot is being offered first to the future owner of 10 Emerson Court, creating a rare chance to preserve the existing secluded environment or thoughtfully expand the property into a private compound with access from both Emerson Court and Fordham Road.

For the buyer who sees the bigger picture, this is not just extra land. It is control, privacy, future potential, and the ability to shape the next chapter of the property.

Enjoy easy living in this 1-bedroom, 1-bath co-op, located just a short walk from the charming Village of Greenport. This move-in-ready home features a newly updated kitchen with modern appliances, a renovated bathroom, and fresh finishes throughout. Perfectly situated to enjoy everything the North Fork has to offer, you'll be just minutes from beautiful beaches, award winning wineries, boutique shopping, restaurants and waterfront attractions.

Stunning vineyard views! Nestled in the heart of the North Fork's first vineyard is this sprawling, historic beauty. Steeped in history but with all the modern comforts and conveniences is the generous estate. Don't miss the one-of-a-kind North Fork sunrises from the primary suite or the picturesque sunsets from the gunite pool. Experience life on a working farm, while enjoying the seclusion and serenity of nearly 66 acres of a classic North Fork vineyard. Completely renovated, never lived in, and to be professionally furnished with designer grade places!

House is at the end of Ketcham Lane. Introducing a Sequestered Post Modern custom designed home. The property backs up to Cove Beach Estates and NYS Ruth Oliva Preserve. This 3 + bedroom home offers high ceilings and sun-filled rooms with high-end hardwood floors throughout. The well maintained property features an inground backyard pool and patio entertainment area, all just a stones throw from the Long Island Sound and the Peconic Bay.

Located in the San Remo Community, North of 25A this charming 2 bed 1 bath Cape Cod is nestled in the heart of Kings Park. This home offers the perfect blend of cozy living and charm. Bright and inviting summer room, expansive deck with winter water views for your own private escape for entertaining or relaxing. All utilities along with roof have been upgraded and are 5 years new.