Courtesy: Engel & Volkers North Fork
631-298-7953
Welcome to your North Fork waterfront oasis in highly desirable Yennecott Park, offering the rare combination of privacy, natural beauty, and effortless access to all. Perfectly positioned along scenic Long Creek with views toward Hashamomuck Preserve, this 4-bedroom waterfront home delivers a relaxed coastal lifestyle. Set on .75 acres with lush mature landscaping and generous water frontage, the property is ideal for kayaking, paddleboarding, sailing, jet skiing, power boating, and fishing — creating a true creekside retreat. Inside, the home features a light filled open layout with thoughtfully designed gathering spaces. The spacious kitchen with stainless steel appliances and ample cabinetry flows seamlessly into the main living areas, while a formal dining room provides an elegant setting for entertaining. The inviting family room is anchored by a wood-burning fireplace, creating warmth and character year-round. A standout feature is the waterside sunroom, offering peaceful water views and the perfect setting for morning coffee, reading, or relaxation. Four bedrooms provide comfortable accommodations, while a dedicated bonus room ideal for a home office adds flexibility. Outdoor living is equally exceptional with two covered porches — one welcoming front porch and one rear porch overlooking the water — allowing for effortless indoor-outdoor enjoyment. The property also offers room for a pool, presenting exciting potential to further enhance the waterfront lifestyle. A spacious, clean basement with high ceilings offers exceptional versatility for a gym, media room, recreation space, or future expansion. Located in Southold’s Park District (use of Founder's Landing facilities on the bay) and near sandy beaches, renowned North Fork wineries, farm stands, marinas, and the shops and restaurants of Greenport Village, this home represents an impressive opportunity for buyers seeking a waterfront primary residence, North Fork second home, or waterfront investment property. Andersen windows and doors throughout, 6 zone inground sprinklers and new CAC in 2025 and new appliances in 2023/2024. 1025 Long Creek Drive is where peaceful waterfront living, location, and long-term value converge.
Courtesy: Douglas Elliman Real Estate
631-354-8100
Soundview on the Vines presents a rare opportunity to own a new construction vineyard-side estate where modern architecture, refined craftsmanship, and the natural beauty of the North Fork converge. Spanning approximately 7,300SF and situated on nearly 2 acres, this exceptional residence has been thoughtfully designed to balance grand-scale entertaining with relaxed, everyday luxury. Upon arrival, a striking foyer sets the tone, leading into a private guest wing featuring multiple ensuite bedrooms, each appointed with spa-inspired baths and generous proportions. This level opens seamlessly to the outdoors, where the covered patio and a heated 20x40 saltwater gunite pool overlook rolling vineyards and open farmland, creating a tranquil backdrop for both intimate gatherings and large-scale entertaining. A well-planned breezeway connecting the mudroom to a three-car garage, while a floating staircase and elevator provide effortless access to all three levels of the home. The upper level serves as the heart of the residence with incredible views and natural light. A custom chef’s kitchen anchors the space, complete with dual islands and premium finishes, flowing naturally into a sophisticated lounge with a statement gas fireplace and an expansive great room ideal for hosting. Walls of glass and multiple sliding doors open to a wrap-around mahogany deck, capturing sweeping vineyard views and allowing indoor and outdoor living to merge beautifully. The primary suite is a private retreat, featuring its own balcony, serene views across the vines, dual custom closets, and a spa-caliber bath with soaking tub and oversized double shower. The lower level offers remarkable flexibility, with additional bedrooms, a full bath, and a generous recreation area adaptable to a gym, media room, studio, or wine storage. Direct outdoor access enhances the home’s connection to its surroundings, while the landscaped grounds provide ample room for future vision—whether it be an outdoor kitchen, accessory building, tennis/pickle ball court, curated gardens and more! Ideally positioned just moments from Long Island Sound beaches and the North Fork’s celebrated vineyards, Soundview on the Vines is a truly inspiring estate where luxury, privacy, and lifestyle come together in one extraordinary setting.
Courtesy: Century 21 Albertson Realty
631-765-3800
Picture this: you’ve been walking through homes that are either way too much house… or feel like a shoebox with a mortgage. Then you walk into this one and it just clicks, not too big, not too small, and it actually makes sense for real life. It’s a two-bedroom layout that works, and the bathroom is basically begging for a remodel. The pink tile had its moment, but I’d happily retire it and put in something that feels like my style. The kind of update that instantly makes the whole house feel fresher without turning your life into a six-month construction zone. What I really love is how you get two different “hangout spaces” Up front, there’s a sunroom that keeps you connected to the neighborhood, coffee in the morning, wave to the walkers, feel like you’re actually part of a community. Then out back you’ve got a deck where you can disappear a little, because it overlooks the woods and the yard is fenced in, The kitchen is the same vibe: totally functional, but also a clear opportunity. Can use it comfortably right now, and then renovate when ready, and the fact that it could be expanded makes it feel like a smart move. And the neighborhood perk? This is the kind you can’t renovate into a house later: the park and beach at the end of the street. In the summer you get that breeze off the water, that easy “flip-flops and go” lifestyle. It’s the simple stuff that ends up being the best stuff.
Courtesy: Century 21 Albertson Realty
631-765-3800
Okay, I have to call you right now because I just walked into a house and I’m kind of… excited? Like, where was this one hiding while we’ve been touring all those “cute but…” places? You know how every other house has been some version of: “Love the idea, hate the layout,” or “Great location, but it feels cramped,” or “Nice kitchen… if you enjoy standing on top of people,” or “Outdoor space… if you count two sad patio chairs and a grill wedged into a corner.” This one is different. First off, it has this wide front porch and the house sits a little elevated from the street, so it immediately feels quieter—like you’re not on display for every dog-walker and leaf-blower within a half mile. There’s a big maple tree, a nice yard, and I swear you can hear the waves rolling from a few houses down. It’s that calm, coastal background sound that makes you feel like your blood pressure just… drops. And inside? The layout is what we’ve been begging for. The kitchen finally makes sense. It’s got the island for prep, but there’s also a separate counter/bar seating area, so everyone can hang out near the kitchen without crowding whoever’s cooking. And the genius part? From the barstools you can still see the TV over the fireplace, so people can snack, talk, watch something, everybody’s in the same space but not bumping elbows like we’re working a brunch shift. Also, remember how I keep saying, “Where do the towels go?” This house answers that. The laundry is right off the kitchen in the mudroom, so beach towels and pool towels go straight in. It’s still laundry, but it’s the kind that doesn’t take over your whole life because the setup isn’t fighting you. Then the main living/dining area is open and it just feels… way bigger than you expect. Like, it has that “everyone can be together” vibe without feeling like one giant echo chamber. It’s actually a real hangout house. Now the bedroom situation, this is where I was like, okay, someone thought this through. There’s a main-floor suite with a walk-in closet and a bathroom that feels legitimately spa-ish: soaking tub, separate shower, and that pebble stone shower floor that makes it feel high-end without trying too hard. And then upstairs there’s another suite, so guests have an actual suite option too—plus two more bedrooms and a full bath, and one of those has interior access so it almost reads like three en-suite options depending on how you set it up. It’s perfect for guests, kids, parents visiting, all of it. And the backyard, listen. There’s a covered porch overlooking the pool, and beyond the fence is this maple forest they can’t build on. That part alone is huge. No future construction ruining the vibe, no “surprise” new neighbor looming over the yard. Just pool, grill, fire pit… and actual privacy. And you get multiple beach choices nearby. Like: a neighborhood sandy beach with picnic tables and sunset breeze vibes, S. Harbour Rd. Beach around the corner—which I think is the widest sandy beach I’ve seen out here, and Goose Creek Beach is only a few minutes away if you want a third option. Plus, because life isn’t just beaches, Croteau Vineyard is close, and it has that French-country vibe and a rosé situation that’s… extremely persuasive. And here’s the practical thing that keeps popping up in our search: it has a full dry basement, and even though you’re near the water, it’s not in a flood zone. That’s the kind of detail that makes you breathe again. Honestly? After all the houses I have seen that needed layout fixes, compromises, or “we could make it work” speeches… this one feels like the first house that already works. And it actually seems priced like they understand current market conditions, not like they’re still trying to cash in on peak frenzy. So yeah. I’m telling you now because if this one checks out the way it feels in person… might finally be done with the house hunting in Southold.
Courtesy: Douglas Elliman Real Estate
631-354-8100
A timeless 1927 shingled cottage set amid lush, established gardens just moments from Horton Point Lighthouse and the Long Island Sound, with a beach at the end of the road. Sun-filled and full of character, the home offers three bedrooms and two baths, highlighted by two original fieldstone fireplaces and a wainscoted sunroom that functions beautifully as a dining space. Thoughtful updates include connection to natural gas, a new dual-zone heating and air conditioning system installed in 2023, an updated kitchen, and new washer, dryer, and refrigerator. Outdoors, mature hydrangeas and cascading wisteria frame a private, fully fenced setting with updated landscaping completed in 2024, creating an open lawn with enhanced privacy. A heated saltwater gunite pool and outdoor shower complete this serene retreat. Enjoy Founders Landing Park District rights with access to both Sound and Bay beaches, along with proximity to North Fork farm stands, vineyards, marinas, boating, dining, and shopping. An enchanting year-round or seasonal escape with an excellent rental history.
Courtesy: Signature Premier Properties
631-647-4880
Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence features three bedrooms, one full bath, and one half bath, along with building plans for a potential second full bathroom on the second floor, allowing the next owner to enhance comfort while preserving the home’s original charm. Original wood flooring and original moldings combined with new windows throughout, updated kitchen featuring granite and marble countertops high end appliances and updated roof lends itself to nostalgic beauty while enjoying modern-day functionality and efficiency. The home has new I-A septic technology. The expansive 4 car garage is an excellent opportunity for car lovers. Ideally situated just moments from the Peconic Bay and Southold’s waterfront, the home provides easy access to beaches, boating, and tranquil coastal living. Downtown Southold Village is also nearby, offering shops, restaurants, wineries, farm stands, and marinas—all within easy reach. With its classic farmhouse proportions, intimate scale, and timeless appeal, this property is perfectly suited as a year-round residence, weekend retreat, or investment opportunity. Set in one of Southold’s most desirable locations, it offers a rare chance to own a piece of North Fork history while thoughtfully planning for the future. A true farmhouse gem—cozy, historic, and ideally located.
Courtesy: Century 21 Icon
631-476-7600
Welcome to 350 Brigantine Drive, a charming Southold retreat set in the peaceful waterfront-community of Harbor Lights where you can enjoy a private beach that overlooks the Peconic bay and Shelter Island. This home offers comfortable living, an inviting layout, and access to all the natural beauty and coastal lifestyle that make Southold so desirable. The main level features a bright and open living area with plenty of natural light, a functional kitchen, and a seamless flow ideal for everyday living or weekend escapes. 3 bedrooms and 2 bathrooms provide comfort and privacy, while the home’s overall layout lends itself to both full-time residency and seasonal enjoyment. Images in this listing have been virtually staged. Outdoors, the property offers a spacious yard perfect for entertaining, gardening, or simply relaxing in the quiet surroundings. Located in a sought-after neighborhood known for its tranquility and proximity to beaches, boating, vineyards, farm stands, and local dining, this home places you at the heart of everything the North Fork has to offer. Whether you’re seeking a year-round residence, a vacation getaway, or a home with long-term potential, 350 Brigantine Drive delivers an exceptional opportunity in one of Southold’s most beloved communities.
Courtesy: Compass Greater NY LLC
516-970-5133
The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the community. Buyers can choose from two options to own this New Construction property: Option 1: Purchase As-Is with Approved Plans – $650,000 This offering includes fully approved architectural plans and Health Department approvals to build a 4-bedroom, 3-bath new construction home on the quiet 0.25-acre parcel at 500 Summer Lane. Purchase the lot as-is and use your preferred builder to break ground on your own schedule. At 500 Summer Lane, you’re less than 1.5 miles from some of Southold’s best gems like Croteaux Vineyard, Goose Creek Beach, Sophie’s Restaurant, and local farm/flower stands. A little further you’ll find the charming Southold Town, Cedar Beach, endless vineyards, Greenport Harbor Brewery, and so much more! Option 2: New Construction Package – $1,400,000 In partnership with respected local builder, this option delivers a thoughtfully designed 2,215 sq ft home that blends timeless details with coastal luxury. Plans include 4 bedrooms, 3 full baths with 9 foot ceilings throughout, creating an airy and elegant space. The first floor of the home features an open-concept kitchen, living, and dining perfect for hosting and easy flow of day-to-day living. Walk up the front porch and enter the front door to a spacious living room accompanied by a warm fireplace for those cooler nights. As you continue you’ll pass through the dining area with floor-to-ceiling doors that look out over the backyard. Enter the brand-new chef’s kitchen featuring a large kitchen island, stainless steel appliances, and beautiful walk-in pantry! The main floor also features a full bath and bedroom, perfect for guests or single-floor living. Upstairs, you’ll find 3 additional bedrooms — 2 that share the full bath in the hall, and a primary bedroom with walk-in-closet and en suite bathroom. Laundry is a breeze with a washer-dryer on the second floor! Outdoors, you’ll appreciate the intentional details designed with North Fork living in mind. The detached garage features a beautifully integrated pool cabana, accessed by a man door. Designed to suit outdoor entertaining and living, the cabana comes equipped with an island bar top, sink, half bath, and space for a grill — the perfect spot to entertain or wind down after a day at the beach with family or guests. The North Fork is Calling Your Name!
Courtesy: Signature Premier Properties
631-647-4880
Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection, honoring the home’s original character while reflecting a level of care and stewardship that is exceptionally rare. From period details and time-honored construction methods, this residence stands as a living testament to Southold’s rich heritage. The interior offers a gracious and functional layout anchored by an enclosed brick porch, a large formal dining room, a newly renovated expansive eat-in kitchen, a classic parlor room, and a comfortable living room—all thoughtfully arranged for both elegant entertaining and everyday living. Adding to the home’s exceptional character are three stunning fireplaces, each serving as a striking focal point and a reminder of the home’s historic craftsmanship. The residence features three bedrooms and two and a half bathrooms. The first floor includes the primary bedroom and two full bathrooms, allowing for convenient main-level living, while the second floor offers two additional bedrooms and a half bath, providing privacy and flexibility for guests . Outside, the property includes a two-car detached garage and is set on a quiet, peaceful lot in close proximity to Southold Bay, offering the serenity of North Fork living with easy access to the water and surrounding natural beauty. With official historic status, this home carries both distinction and prestige—appealing to discerning buyers who value provenance, integrity, and timeless elegance. Opportunities to own a property of this caliber, condition, and historical significance are exceedingly rare. This is more than a home—it is the stewardship of a true legacy. ** NOTE: The legal address for this home is 3500. However, the number on the post outside the home is 3290. CPF Tax/The Peconic Bay Region Community Preservation Fund applies to this listing.**
Courtesy: The Agency Northshore NY
631-870-0753
Dream big, live LARGE! This newly renovated home is ready for it's close-up! The new Chef's Kitchen is designed with easy summer hosting in mind, with new appliances, gorgeous counter-tops and a Hamptons vibe. Large open plan living room with a wood-burning fire-place, and large dining area are ready for your whole tribe! All of the upstairs bedrooms (including the primary suite) have a shared balcony that overlook the pool and grounds. Plus, so much bonus space that it really must be seen to be believed! The beautifully renovated In-law suite in the walk-out basement makes summer hosting hassle-free. Set on a park-like property that boasts a spa-like heated saltwater pool, water slide, pizza oven, areas for sports, a built-in fire pit and so much more!
Courtesy: Daniel Gale Sothebys Intl Rlty
631-288-1050
Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum structural integrity, energy efficiency and elevated finishes throughout. The sleek open-concept design encompasses approximately 4,500 square feet of living space. The light-filled residence showcases curated architectural features, ranging from floor-to-ceiling glass, floating staircases, bluestone and covered patio, water-view balcony, and a walk-out lower terrace. The Modern custom kitchen is adorned with ceiling-high cabinetry, Thermador appliances, marble countertops and porcelain inlay backsplash. The adjoining great room is anchored by a stunning gas fireplace surrounded by textured porcelain and this main level also includes an office, dining room and junior en-suite offering private access to the water and soon to be built saline heated pool. An upper level primary en-suite includes a private balcony and three additional spacious bedrooms, luxury baths, laundry and unfinished bonus space. The lower level offers 2,000 square feet for new owners to reimagine and personalize. The offering is complete with Founders Landing Beach, wineries, farm to table dining and a vibrant North Fork atmosphere.
Courtesy: Century 21 Albertson Realty
631-765-3800
You know we have been looking at new homes for a while. This one is the first that felt like, "okay, this checks the boxes" The granite front porch sold me right away. wine and cheese with everyone and with the larger width and depth, you can see they built the home with this in mind. And the kitchen is exactly what I wanted because this is where we all hang out and this has the built in refrigerator, freezer, double ovens with the pantry right there, and the island is set up so your not doing that awkward "move over" dance. And I have never seen this before, a 45" workstation sink is genius. Two people can actually use it without elbow wars. Then you see the laundry room and it's amazing. In this 5 bedroom house you have 4 slide out drawers to hold the 4 laundry baskets and since they have a set place, the room stays organized. It also has a pet washing station with slate floors and tiled walls it's just a smart use of space. The main floor suite is perfect, and the walk in closet has lighting right on the hanger bars so you can actually see everything. The bathroom has a curbless shower shower, built in bench, dual vanities and a toto wash-let toilet. It is not every house that has these features. The finished basement doesn't feel like a basement as it has big windows, double doors out to the pool stairs, bright and open. It's set up for movie nights with Savant controlled speaker and media throughout the house, a beverage center, and even a steam shower down there. Upstairs you have another primary suite as well as two more bedrooms with baths so the layout works so well. Outside is straight up resort mode. Covered granite porch with wall-wash lighting, speakers, a pool with a 6" swim deck for in water lounge chairs and umbrellas, sheer descent water feature and bluestone patio and walkways, all the low maintenance stuff we actually want. And the location is perfect for getting people out of the house. The neighborhood has a path to Goose Creek with kayak and paddle board racks to jump on the water and head over to the sandy beach at Goose Creek beach. This is also 15 minutes to South Harbor Rd beach without the car and Croateux Winery. iconic for the French country vibes is basically just around the corner.
Courtesy: Douglas Elliman Real Estate
631-477-2220
Seasonal Condo Near a Memorable Long Island Sound Beach (Town Beach). Studio Apartment with Efficiency Kitchen and is Located on the 2nd Floor. The Condo Offers a Community Room, Lawn with BBQ Area, Laundry, Off Street Parking, Boat Storage, Beach Storage. Electric, Water, Cable and Sewer/Cesspool included in Common Charge of $253 Monthly. SEASONAL CONDO OPEN APRIL TO NOVEMBER. NOT YEAR ROUND.
Courtesy: Thomas J McCarthy Real Estate
631-765-5815
Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporary home offers wide-open water views, beautiful sunrises and sunsets, and a seamless indoor–outdoor flow. The light-filled main level features a newly built modern kitchen that opens directly to the outdoor entertaining area, along with a waterside first-floor primary suite. Large windows invite the views in, creating a relaxed, airy atmosphere throughout the home. Outside, the property lives like a private shoreline retreat. Enjoy the new heated saltwater pool with automatic cover, an enclosed outdoor shower, and generous patio space perfect for lounging or hosting. The private dock provides more than just waterfront enjoyment—there’s direct boating access to Southold Bay and Peconic Bay, with easy routes to Greenport, Shelter Island, and even Sag Harbor for dining, marinas, and day trips. A turnkey waterfront residence that blends comfort, modern updates, spectacular views and the best of coastal living!!!
Courtesy: Douglas Elliman Real Estate
631-354-8100
Welcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart of the North Fork's Town of Southold. This home is situated on .80 acres & boasts 4,327 SF of living space with 4 bedrooms and 4.5 baths and combines clean lines of modern design with the allure of North Fork chic. This home comes with Authentic Western Red Cedar Shingle siding and a stucco accented stair tower that makes the grand foyer rise into the second story. There are 9ft high ceilings on the first and second floors in addition to vaulted and coffered ceiling details with 8-1/2” white oak floors throughout. Enjoy two bedrooms on the first-floor which includes a primary bedroom with a generous walk-in closet and private access to the masonry patio opening to the backyard pool and garden. The great room contains a 46” linear gas fireplace and is open to the well-appointed kitchen which includes custom inset cabinets, marble countertops and high-end GE Monogram appliances with a wet bar. The second floor has two bedrooms both ensuite with large tile and custom vanities. The second floor also contains a beautiful family room and a large laundry room with custom cabinetry and a sink. The basement can be finished to suit which includes 9’ ceilings. Enjoy the incredible entertainment ready backyard featuring a 20X40’ heated gunite saltwater pool, including automatic pool cover with a Napa Stone marble patio. The secluded backyard includes custom designed landscaping and masonry by our Landscape Architect.
Courtesy: Douglas Elliman Real Estate
631-354-8100
Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives on connectivity and convenience. Just moments from your doorstep, you’ll find the local bus and train station, making your commute or weekend trips a breeze. Additionally, this location places you in close proximity to a variety of local shops, offering everything from everyday essentials to unique finds. Schedule your showing today and do not run the risk of missing out on this fantastic opportunity!
Courtesy: Daniel Gale Sothebys Intl Rlty
631-734-5439
Southold-West Creek Estates - Beautifully appointed, light-filled home. Recently completed with attention to every detail. A wood and glass front door and natural wood architectural accents set the tone at the front entrance. The large great room features a living area with a two-sided gas fireplace, dining area, and a generous chefs eat-in kitchen. The second side of the fireplace faces the covered rear porch. All spaces share a wall of windows and doors opening to the rear porch, enhancing the indoor/outdoor flow that is perfect for entertaining. The expansive kitchen features quartz countertops, a custom tile backsplash, a huge island, and stainless Bosch and XO appliances. A dream kitchen for cooking and hosting. A first-floor primary bedroom with a stunning marble bathroom and doors and windows that open to the rear porch and face the lovely pool and yard. Also on the first floor is a large state-of-the art media room with a 98-inch screen and sound system. A laundry room and powder room complete the first floor. Upstairs are three ensuite bedrooms, an office nook, and a sitting room that opens to a spacious roof deck with water views. This home features spacious rooms bathed in natural light and wood floors throughout the house. 4 zone Sonos built-in sound system. Full basement with 9' ceilings and 3 egress windows. The half-acre property is beautifully landscaped with specimen plantings and new stone walkways. The covered rear porch offers shade and access to the 18' by 36' heated salt water swimming pool. New limestone hardscape surrounds the pool. Attached two car garage with electric vehicle car charger. Access to Southold Park District beaches. Restaurants, golf, beaches, shopping, farm stands, wineries, breweries, and boating are all right here. If you are looking for a luxury, move-in ready home perfectly situated for you to enjoy the North Fork experience, this house checks off all the boxes.
Courtesy: Corcoran
631-765-1300
Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany front door and decking, solid wood closet systems, bespoke pantry shelving, and a handmade stone mantle and hearth. This lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with Bertazzoni and Bosch appliances, extra large island and breakfast nook, formal dining room with Butler's pantry, first floor junior primary ensuite, and library. Upstairs is a spacious primary ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar, gym or other uses. Outside enjoy multiple covered porches and your lovely pool, all surrounded by the peace and quiet of this serene and private setting. This is truly a Hampton-style masterpiece on the North Fork.
Courtesy: Corcoran
631-765-1300
Southold Sanctuary There's a certain ease to life on the North Fork and knowing you are never far from the water - where summer stretches into fall, where neighbors still wave, and where the days' quiet rhythm becomes your soundtrack. Welcome to 4,173 square feet of newly built grace on just under a half-acre in Southold and one mile to Goose Creek Beach and two miles to Cedar Beach. This isn't your typical new construction. It's what happens when thoughtful design meets coastal sensibility - select red oak floors underfoot, light pouring through every room, and a 20x40 custom Gunite, heated saltwater pool framed by wide porcelain pavers that seem to dissolve into the landscape. A firepit means those October evenings by the pool aren't just possible - they're inevitable. This home is built for entertaining! And when you do, the kitchen is where this home really speaks: Galiano Moena 36" gas range, double wall ovens, counter-depth refrigerator, a wine cooler, and quartz countertops. The main floor boasts a primary suite that provides a private retreat, complete with a walk-in closet and an en-suite bath, ensuring a serene escape. Additional conveniences include a laundry area, a covered porch, a rear deck, and an attached two-car garage, enhancing the ease of everyday living. Three generously sized bedrooms offer ample space for guests, complemented by walk-in closets and two full bathrooms for added comfort on the second floor. Need more space? A fully finished basement featuring a wet bar with its own beverage fridge, a theater room, a large recreation room and another possible bedroom with bathroom means this home checks every box for that peaceful North Fork state of mind!
Courtesy: Serhant East End LLC
631-500-8800
2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find — a welcoming home in a peaceful setting. There’s a sandy neighborhood beach right across the street and it’s positioned near other beaches, marinas, and North Fork vineyards. Located in a highly desirable Southold waterfront enclave, the property presents a compelling opportunity for both lifestyle buyers and long-term investors. Benefitting from strong seasonal demand and limited inventory in the immediate area, this 1.03-acre property represents not just a purchase — but a strategic hold in a supply-constrained coastal market. Beautifully updated and maintained, the two-bedroom, one-bath cottage features a cozy fireplace and gleaming hardwood floors, complemented by a recently renovated kitchen, glassed-in Florida room, central air, unfinished basement and a solid amount of upstairs bonus room space. Additional highlights include a generous two-car barn, lengthy circular driveway, and a serene park-like setting that enhances the overall appeal of this special property. Secure today. Appreciate tomorrow.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-734-5439
Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen, and entertainment nook, it’s made for barefoot mornings and breezy afternoons with friends. Step outside to a spacious wraparound deck and 130 feet of pristine waterfront — perfect for soaking in the sun, launching a kayak, or simply taking in the view. Secluded yet steps to the private sandy association beach, this is a rare slice of coastal paradise where summer never really ends.
Courtesy: Compass Greater NY LLC
631-251-8644
Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential. The enormous attic, featuring 8.5+ ft ceilings, offers the possibility of a third-floor buildout. The walk-out basement, with 9+ ft ceilings, two egresses, and plumbing in place, adds even more room for customization. Resort-style amenities continue across the grounds: a 16' x 32' heated saltwater gunite pool with electric cover is set into a 2,100 SF deck, a high-end 6-person hot tub and an outdoor shower. A wide path leads to a fire pit area and the private dock, which previously accommodated a 23' Grady-White and provides direct access to the bay. Inside, a chef’s kitchen, wood-burning fireplace, and generous ceiling heights enhance the home’s warm yet refined ambience. Radiant heat warms the eat-in kitchen, all bathrooms, and additional spaces throughout. Recent upgrades include the new pool and hot tub, a newly constructed circular driveway, freshly painted Hardie board siding, all-new interior paint, updated lighting, and modern hardware. A truly exceptional offering of space, serenity, and waterfront luxury—ideal as a full-time residence or a memorable seasonal escape.
Courtesy: Douglas Elliman Real Estate
631-354-8100
North Fork Coastal Living With Sunset & Water Views Enjoy breathtaking sunsets and water views from any of the three private balconies of this beautiful North Fork retreat. Designed for comfort and relaxed elegance, this residence features a dynamic open floor plan that seamlessly connects the living room, dining, and kitchen areas leading to outdoor balconies. The granite kitchen is perfect for entertaining, opening to a bright living room with a fireplace and a cozy den ideal for year-round gatherings. The first-floor primary suite offers convenience and privacy, while upstairs you’ll find two additional bedrooms, each with its own balcony overlooking the Long Island Sound. The fully finished walk-out basement extends the living space with direct access to the patio and backyard, ideal for outdoor dining or relaxing in the coastal breeze. A detached two-car garage includes a bonus room for extra storage above, offering generous space for a studio, office and many other possibilities. Perfectly located near McCabe’s and Kenney’s Beaches, local vineyards, the lighthouse, and North Fork’s favorite restaurants, this home captures the essence of seaside living — where every day feels like a getaway.
Courtesy: BERKSHIRE HATHAWAY
631-642-6212
Location! Location! Sits this fabulous to be built home located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to own this exceptional property: Option 1: Purchase As-Is with Approved Plans – $1,550,000 Prefer to build on your own schedule or with your own team? The existing home is also available as-is for $1.55M. This includes: Fully approved architectural plans, Ready-to-issue building permits, .37-acre lot on a quiet canal with private dock, Prime opportunity to invest in a trophy location with a head start on construction. Whether you're ready to break ground now or planning for the future, 535 Bay Home Road is a rare chance to own on one of the North Fork’s most prestigious waterfront streets — just steps to a private beach and directly across from a scenic vineyard. Option 2: New Construction Package – $3,300,000 Partner with the highly regarded North Fork Building Company to create a custom 2,900 sq ft modern waterfront home, expertly designed to showcase water views and deliver a luxurious coastal lifestyle. Planned Features Include: 3 en suite bedrooms, Additional full bath off the mudroom, Main-floor flex room (ideal for a 4th bedroom, home office, or den), Heated waterside pool, Covered outdoor living room with kitchen and wood-burning fireplace, Private dock + floating swim dock ,Detached two-car garage with unfinished attic space Interior Highlights: Gourmet kitchen with custom cabinetry, quartz countertops, Thermador appliances, Gas fireplace in the living room with custom built-in bookcases, 10’ ceilings on the main level, 9’ ceilings upstairs, White oak flooring throughout, Kohler fixtures, Andersen windows, and recessed lighting, Custom molding package, Walk-in closets in all bedrooms, Upstairs laundry room, With final plan approvals nearing completion and permits ready to issue, now is the ideal time to customize your finishes and build your North Fork dream home. *Licensed real estate salesperson has ownership interest in KIMDY Realty LLC, the seller*
Courtesy: Thomas J McCarthy Real Estate
631-765-5815
Wake up to breathtaking panoramic views of Peconic Bay from your own private waterfront retreat! With 160 feet of shoreline and a 6'x20' dock, this property is a dream for boaters, beach lovers, and anyone craving coastal serenity. Inside, there’s room for everyone with 5 bedrooms, 2 full baths, and a sunlit loft. The wraparound deck invites you to savor spectacular sunrises and sunsets, entertain guests, or simply unwind with the soothing sea breeze. Located in the beautiful Bayview section of Southold, you're just moments from Cedar Beach, and surrounded by the best of the North Fork—award-winning vineyards, charming farmstands, and top-rated restaurants. This property won’t stay on the market for long!
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.
