This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage. The home currently has tenants, who will be leaving.
Okay, so the first thing, you get out of the car and this farmhouse style has the front porch that actually has room for a side table and chair to have my morning coffee in peace that I have wanted so badly. Then inside, the half bath is right next to the front door, but it's tucked far enough away from the open living room and kitchen that it doesn't feel awkward when all of us are hanging out. The kitchen has the paneled fridge, a real pantry closet and open shelves that I have always liked. The kitchen sink is setup where I am staring out to the backyard when I am stuck doing dishes, so good. They even say there is room for a pool. Then the dining room has this full glass slider to the yard, so the whole back of the house is just filled with light, you can even see the view of the yard from the living room. Upstairs, the ensuite bathroom is honestly my favorite surprise, the floor is so interesting, and the whole space feels calm with the finishes they picked. Even the downstairs bathroom has this beautiful wallpaper that makes this new construction feel intentional, not an afterthought. What I love is this location makes you feel like you found a secret corner of Greenport. You're literally tucked up against the maple tree forest, so it's quiet and green in the best way. The backyard is fully fenced so if the decision is for the pool, it doesn't feel tight. And because this one is New Construction, everything just feels solid and reliable. Best part, the house is also a half mile away from the LIRR train station and Hampton Jitney stop to get to NYC. I think this might be the one, you have to come see it.
Designer Modern Farm Ranch set on over 3.35 Acres with farm and scenic views. Renovated 2023. Open concept Living Room, Dining Room and Kitchen, Gorgeous Kitchen with quartz countertops, Stainless Steel Appliances, built in Wine Cooler, New Windows throughout, New Interior Doors, New Exterior Doors, Custom Closets, New flooring, updated Designer Baths, New Boiler, New Well Pump, New Hot Water Heater. Spectacular 20x40 Inground Saltwater Pool with Cambridge Paver Patio. Covered Front Porch overlooking Farm Views. Access Resident Only Town Beaches, Boat Ramps and Parks with Town Permit. Close to McCabe Beach for Incredible Sunset Views. Marina, Airstrip and Trails nearby. Farm animals permitted. Possible Sub-division. New, New New, Priced to Sell.
A bright and thoughtfully designed farmhouse in the heart of Cutchogue. Reimagined in 2017, the home underwent a comprehensive renovation that carefully blended its original charm with the modern conveniences of everyday living. Set on a beautifully landscaped and private shy half-acre, the property offers ample room for a pool and additional outdoor amenities. The renovation resulted in a substantially rebuilt and expanded residence featuring four bedrooms, 2.5 baths, and a flexible floor plan well-suited for both entertaining and relaxed year-round living. A generous wraparound front porch sets the tone for seamless indoor/outdoor living, while one of the North Fork’s most beloved bay beaches is located just a minute down the road. A rare opportunity to own a thoughtfully updated North Fork escape in an exceptional Cutchogue setting.
Set in the heart of Orient’s bucolic Browns Hills, this light-filled contemporary residence offers an exceptional blend of privacy, design, and landscape. Expansive views stretch across open pastoral fields to the bay beyond, creating a setting that feels both peaceful and uniquely North Fork. Spanning three levels, the home features a highly functional floor plan with three bedrooms and three baths, thoughtfully arranged to provide flexibility and comfortable separation of space. Large windows and multiple exposures fill the interior with natural light while framing the surrounding scenery throughout the day. Outside, beautifully developed landscaping surrounds a heated saltwater gunite pool, expansive decking, and outdoor shower, creating an ideal environment for entertaining or quiet summer living. Association access to your Sound Beach completes the offering, adding easy waterfront enjoyment to this serene Orient retreat.
Just 150 feet from a private association bay beach, and completely reimagined and renovated in 2018! This pristine ranch offers the ease of single-level living, the luxury of modern updates, and the warmth of timeless charm—all paired with an exceptional beachside lifestyle. The home was renovated in 2018 and features a beautifully updated kitchen and bathrooms, refinished wood floors, new carpeting in the bedrooms, new mechanicals, including a propane gas boiler, central air conditioning, insulation, a generator, and some new windows. This stylish 3-bedroom, 2-bath residence includes a spacious primary suite with an ensuite bath and walk-in closet. The tastefully designed kitchen showcases high-end cabinetry, quartz countertops, and bar seating for four, with an open-concept layout that flows seamlessly into the dining and living areas. The inviting living room retains its original craftsmanship and character, highlighted by a cozy propane fireplace, while thoughtful upgrades throughout provide comfort and efficiency. A bright home office with abundant natural light offers flexibility as a multipurpose space. One of the home’s standout features is the oversized 290 sq ft screened-in porch—perfect for relaxing after a day at the beach, entertaining guests, or unlocking additional potential. Enjoy outdoor living with a beautiful backyard yard, featuring a patio installed in 2018, and charming gardens. A full basement provides ample storage, and a rental permit adds excellent investment potential. Partial furnishings potentially available to be negotiated into deal or sold separately. Private Indian Neck Park Association. Located just 150 feet from the entrance to the private bay beach, this home is the ideal summer getaway or fabulous year-round retreat.
Southold chic Soundfront escape in one of the area’s most desirable locations, offering sweeping water views, sensational sunsets, and effortless North Fork living. Renovated in 2016 and move-in ready, this stylish waterfront retreat is designed for both entertaining and quiet moments by the sea. Inside, thoughtful upgrades include under-floor heating, ducted heating and cooling with remote access, marble countertops, updated mirrors and light fixtures, keyless entry, Sonos speakers, and a chef’s kitchen. The primary suite features an egg-shaped soaking tub perfectly positioned to capture the sunset views. Outdoor living defines the property, with a huge sun deck for dining, lounging, gatherings, or yoga, plus stairs leading directly to the beach. The rare grandfathered lower waterfront platform offers an extraordinary setting at the water’s edge for cocktails, Pilates, or simply taking in the Sound. The outdoor sound system extends the experience all the way to iconic Whale Rock in the water. Additional highlights include an outdoor shower and a garage with potential for conversion to additional living space with proper permits. With dramatic water views, unforgettable sunsets, and a lifestyle centered around the Sound, this is North Fork waterfront living at its best.
Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set on nearly a full acre, the property is an entertainer’s dream with a heated saltwater pool, outdoor shower, and a screened-in porch ideal for summer evenings. The home also boasts a 3-car garage, whole-house sound system, security system, elevator, and a full irrigation system that keeps the grounds lush and green. Gorgeous landscaping with landscape lighting throughout. High-end construction materials and thoughtful design elevate the entire living experience, with 8-foot ceilings in the basement offering the perfect opportunity to create a media room or home gym. Enjoy spectacular sunsets, unbeatable beach access, and the potential to easily add a pool house—water and electric are already in place. This is coastal living at its finest.
Welcome to this One-of-a-Kind 4-Bedroom, Custom Built Colonial, Beachfront Property, ideally located on the North Fork of Long Island along the Beautiful LONG ISLAND SOUND! True Meaning of LOCATION! This Spectacular Waterfront Home offers Breathtaking Panoramic Views, Direct Beach Access (Southold Beach), and the Perfect Blend of Privacy and Coastal Charm. Wake up to Stunning Sunrises and the Sound of Waves! This Beachfront Colonial Home also Features a Spacious 4th Bedroom on the 3rd Floor with Amazing Water Views! Hardwood Floors in all 3 Bedrooms! Two Full Bathrooms, inside you'll walk into the Livingroom with a Custom Granite Fireplace, A Formal Dining Room Surrounded by Water Views, And An Eat-in-Kitchen with a side door to the Wrap Around Deck Overlooking Southold Beach! High Hats Throughout, Brand New Boiler with 2 Heating Zones, 200 Amp Electric, Built on a Pile Foundation which includes a Stand-Up Crawl Space with Plenty of Storage and a Retaining Wall ! Visit the Many Wineries and Farms, Minutes away from the Historic Maritime Village of Greenport ! Experience True Beachfront Living in one of Long Island’s most sought-after locations, A Rare Opportunity to own an Exceptional Home where Every Day feels like a Getaway.
Discover this rarely available Pheasant Run Condo in Greenport. This desirable 2-bedroom, 2-bath, single-level condo features a bright eat in kitchen, a spacious living room with sliders opening to a private deck, and a full basement offering abundant storage. Features include a primary bedroom with an en suite bath, in addition to a comfortable guest bedroom and full guest bath. Ideally situated just steps from the community Clubhouse and pool, the condo also offers easy access to Greenport Village, beautiful beaches, local vineyards, and convenient transportation options. With low taxes and affordable monthly maintenance, this is an exceptional opportunity to own in one of Greenport’s most sought after condo communities.
Stunning new-construction coastal retreat with modern luxury and unmatched entertaining spaces. This bright, modern farmhouse offers a covered front porch, designer kitchen with upgraded appliances featuring a 48" Viking stove, and seamless flow into spacious living areas. Two primary suites — one on the first floor and one on the second — plus spa-like full bathrooms provide comfort and privacy. Indoor/outdoor living is exceptional: a 20 x 40 inground pool set in pavers, fire pit seating, a tiki bar, wet bar and half bath outside. Ideal for gathering. The living room showcases a dramatic 60' gas fireplace. A whole-house entertainment system with indoor and outdoor speakers, integrated cameras and smart-home features makes hosting effortless. Community amenities include deeded beach rights just a two-minute walk away, a community boat ramp and kayak storage. Wineries, farmstands and public beaches are all within a pleasant 10-minute bike ride. Turnkey, high-end finishes and premier location — perfect for coastal living and entertaining.
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.
This light and bright three-bedroom, three-bath home in Willow Point has been thoughtfully cared for by its original owner since being built in 2003. Located just a few hundred yards from a sandy bay beach and featuring a privately owned deeded boat slip, the property offers meaningful water access rarely found at this price point. With its comfort, convenience, and true North Fork lifestyle amenities, this is a move-in-ready opportunity in a coveted waterside community. Inside, an open floor plan creates an easy flow between the main living spaces, while spacious bedrooms, abundant natural light, and an oversized garage add to the home’s everyday functionality. Outdoors, a large deck provides ample room for entertaining or relaxing after a day on the water. Ideally positioned between Greenport Village and Southold an surrounded by many of the North Fork’s best farm stands, wineries and restaurants, this is a move-in-ready opportunity in one of the region’s most desirable waterfront-adjacent communities.
Lovely, fully updated beach house with deeded beach rights set on a private road which ends at the water 300 feet away. It has an open floorplan with vaulted ceiling, a gas fireplace and its chef’s kitchen is a culinary delight equipped with granite countertops, stainless steel appliances and gas double oven. The home has 3 bedrooms and 2 full baths which have brand new tile surrounds and new tiled floors. It has mini-split ductless CAC/Heating from a heat pump which also provides “on demand” hot water. Out back is a large two car garage with an attached outdoor shower. The yard is very private with specimen plantings and a brand new rear deck backed by charcoal pea gravel making the yard and easy-care oasis. Additionally it has a new washer and dryer as well as a plug-in for electric vehicles. The location is close to wineries, golf and restaurants as well is the rest that the North Fork has to offer. Come see it soon!!
This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.
Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a .52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom and three second-floor ensuite guest rooms. The interior is designed for both comfort and entertaining, with a two-sided gas fireplace, quartz kitchen countertops, Bosch and XO appliances, dimmer lighting throughout, electric shades in key living areas, ceiling fans in all bedrooms, and a first-floor laundry room. Home includes 7 built-in TVs, a 98-inch Sony screen and home theater with blackout shades, creating an impressive entertainment space. Since purchasing, the owner has elevated the property, including full front and rear landscaping, new lawns, extensive plantings, 73 trees, a new front walkway and steps, a rear sprinkler system, outdoor accent lighting, and a limestone patio surrounding the pool. The exterior is anchored by an 18x36 gated heated saltwater pool with a 500-gallon inground propane tank for the pool heater, a rear porch, dog run, retaining wall, and roof deck with water views. Additional features include a Sonos music system inside and out, alarm system, 2-car attached garage with shelving, additional refrigerator, and electric car hookup. Ideally located in Southold, this move-in-ready home combines new construction ease with substantial post-purchase improvements already completed.
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.
Clad in cedar and built with meticulous attention to craftsmanship, this brand-new custom home sits proudly on a generous 0.59 acres, just moments from downtown Cutchogue. Timeless in design, the heart of the home is a striking open-concept kitchen with beautiful cabinetry, an oversized island, and seamless flow into a light-filled dining area overlooking the expansive backyard. The living room, anchored by a fireplace, features custom millwork and opens to a covered bluestone porch, creating an easy connection between indoor and outdoor living. First-floor highlights include a large primary suite with an ensuite bath and large closet, an additional ensuite guest bedroom and a laundry room. Upstairs, a spacious second primary ensuite and two additional ensuite guest bedrooms sit across from a very large recreation room, perfect for movies, gym or office. A two-car garage with heated floors adds both function and flexibility, while the full-height basement with egress offers future expansion potential. Located in the heart of the North Fork, just minutes from golf, farm stands, wineries, restaurants, schools, and many of the region’s most sought-after amenities.
Cutchogue Farmstead. Ideal North Fork location. This property includes the home, a 2600 sf barn with horse stalls, water and electric, outbuildings, and 4.5 acres of vines planted in Merlot, Sauvignon Blanc and Riesling varietals. This 1800's restored farmhouse is set on 17.5 acres of level, fertile land. Development rights are intact offering not only agricultural potential but also subdivision and other options. The farmstead's manageable land size is suitable for an eco-friendly, entry level enterprise and also offers additional acreage to an established owner looking to increase crop production. The 3BR, 2 BA farmhouse has a lovely, covered porch with a Western exposure, great for afternoon get-togethers. A patio with a pergola overlooks the planted vines. Opportunity abounds in this 17.5-acre, development rights intact property in Cutchogue, the sunniest place in New York State. REALLY! Central, accessible North Fork location. Bring your concept to life here.
Welcome to the charming and historic, circa 1760, Mattituck farmhouse, updated and renovated throughout the years while still featuring historic details, including original wide-plank wood flooring, exposed wood beams and period details. There are six fireplaces throughout the home, including one in each of the three bedrooms, the downstairs den, living room and dining room. The first floor offers two kitchens, a den, living room, formal dining room and butlers panty and wet bar. Between the renovated kitchen with a gas cooktop and original, working brick beehive oven is sunlit butler’s pantry with glass-front cabinetry, rich wood countertops, small sink, wide-plank floors, wet bar and beautiful vintage character. The second kitchen also features a walk in pantry, two doors to access the front or rear yard and a dedicated laundry area. Both kitchens lead to the formal dining room with a half bathroom off of the hallway. In addition, there is a brand new 4 zone furnace and hot water heater in the basement. The second floor offers three spacious bedrooms, all with their own fireplace and the primary bedroom has an expansive walk in closet, formerly used as a small adjacent room. There are two full bathrooms on the second floor and one of the guest bedrooms features built in bookcases and a lounge area with a couch and coffee table next to large windows. Heading to the third floor, you will find two additional finished bonus rooms, also with original hardwood flooring. Finally, going to the fourth level, there is unfinished attic space with a 7 foot peak to the roofline, providing plenty of space to move around. Outside, you will find meticulously landscaped grounds and gardens, two stone patios, mature and healthy trees and a two-story carriage house that is set for a studio, workshop, garage or whatever fits the new owners needs. There is plenty of room for an in-ground pool to be situated in the backyard without taking away from the already mature variety of shrubs, flowers and trees.
Designer-owned and newly renovated, this exceptional North Fork retreat seamlessly blends modern sophistication with timeless coastal charm. Perfectly positioned across from pristine protected land and a scenic golf course, the home offers tranquility, privacy, and effortless access to the very best of Cutchogue living. If you love golf, you are steps to Cedars Golf Club and can play every day. Ideally located just moments from the charming village center, enjoy easy walks to town, local shops, restaurants, and the Hampton Jitney with direct service to Manhattan. Spend your days biking to nearby New Suffolk, renowned North Fork beaches, acclaimed vineyards, farm stands, and waterfront dining. Just 85 miles from Manhattan, and perfect location with no need for a car. Bathed in natural light, the thoughtfully designed interior features hardwood floors throughout and an open, airy floor plan ideal for both relaxed living and elegant entertaining. The spacious first-floor primary suite is a true sanctuary, complete with a spa-inspired en-suite bath featuring a soaking tub and refined designer finishes. A second guest bedroom on the main level offers flexibility for visitors or home office use. At the heart of the home is a stunning chef’s kitchen appointed with premium stainless steel appliances, dishwasher drawers, deep porcelain sink, and an inviting eat-in dining area highlighted by a Serena & Lily chandelier. The oversized living room with a sleek modern electric fireplace flows effortlessly into the separate dining area, creating the perfect setting for gatherings year-round. Upstairs, two generously sized bedrooms with a beautifully appointed en-suite bath, offering comfort and privacy for guests. Outside, professionally landscaped grounds bloom with lush flowers and mature plantings, while the covered porch provides the perfect backdrop for alfresco dining and summer evenings. The expansive backyard features room for a 16x32 heated saltwater pool, creating a true resort-like atmosphere. The Pool permit is already secured and can be installed for this summer. Additional highlights include a large basement, oversized two-car garage, and new furnishings available separately for a completely turnkey experience. Whether seeking an upscale summer escape, luxurious year-round residence, or exceptional investment opportunity, this move-in-ready home embodies the very best of North Fork living. New owner can immediately rent for the summer if desired.
North Fork living, refined. Welcome to Wildberry. A newly constructed residence where design, light, and landscape converge - set against sweeping, sunset vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its surroundings. Luxury finishes have been selected and wired for full smart home capability. Intuitively designed for both everyday living and elevated entertaining. Offering 5 bedrooms and 5 full bathrooms and one half bathroom, the layout balances scale and comfort, providing a private retreat while accommodating guests with ease. Featuring two primary en-suite bedrooms on both the first and second floors, three guest bedrooms and a full cabana-style bathroom in the walk-out basement for pool party guests. Salt water pool is 18x36 and surrounded by patio with outdoor kitchen. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork. Home is expected to be completed July 2026, photo is artist rendering, landscape design is rendering not actual, additional photography and information coming soon.
Located in coveted Rock Cove Estates in Greenport, this beautifully maintained cedar shake and stone residence offers the perfect blend of privacy, comfort, and North Fork lifestyle. Built in 2007 and lovingly cared for by its original owner, the home features four bedrooms and three full baths, including a spacious primary suite with well-appointed bath with double sinks, Jacuzzi tub and separate shower. The primary bedroom also includes large closet and area for home office. The main level offers warm and inviting living spaces, including a living room with wood-burning fireplace, a library, an updated kitchen with induction stove, new backsplash, newer dishwasher and wood floors throughout. Thoughtful upgrades include natural gas conversion, two-zone systems, Nest thermostats, 200-amp electric, security system, mature landscaping and irrigation system throughout property. Set on a fully fenced property with room for a pool, the home also includes a two-car garage with epoxy floor and an outside entrance to the basement, offering excellent functionality and storage. Residents of Rock Cove Estates enjoy deeded private beach rights with key access! A rare opportunity to enjoy a beautifully maintained Greenport home in one of the area’s most desirable communities.
Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

Southold is located in New York. Southold, New York has a population of 23,571. Southold is less family-centric than the surrounding county with 21.26% of the households containing married families with children. The county average for households married with children is 32.94%.
The median household income in Southold, New York is $92,229. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Southold is 56.1 years.
The average high temperature in July is 80.9 degrees, with an average low temperature in January of 23.6 degrees. The average rainfall is approximately 48 inches per year, with 27.3 inches of snow per year.