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$5,995,000
5 Beds ⋅ 5 Baths ⋅ 999173 MLS
Welcome to 920 Cedar Point E in Southold, a spectacular 1.4-acre waterfront estate overlooking one of the most breathtaking stretches of the Peconic Bay, complete with a private deeded dock slip just steps from the property. Featuring 200 feet of pristine sugar-sand beachfront, this exceptional setting offers privacy, serenity, all-day sunshine, and the gentle prevailing southwest breezes for which the Peconic Bay is known. As day turns to evening, breathtaking sunsets create an ever-changing display of color across the water before giving way to a starlit night sky. Designed to complement its remarkable surroundings, the cedar-shake residence stretches across the property's 200 feet of waterfront, positioned remarkably close to the Bay while protectively perched approximately 25 feet above sea level. From nearly every vantage point, the home offers a front-row seat to a uniquely nautical backdrop of passing boats, maritime activity, and local wildlife. Inside, the approximately 3,500-square-foot, five-bedroom, four-and-a-half-bath home is light and airy, with wide-plank wood floors and generously scaled living spaces. A more recently added Great Room features soaring, sun-soaked ceilings and is anchored by an oversized fireplace, creating an inviting gathering space with a strong connection to the surrounding landscape. The primary suite is truly one of a kind, extending even closer toward the water's edge and capturing panoramic Bay views from nearly every angle. The spa-like en-suite bathroom is equally captivating, perfectly framed by an ever-changing canvas of sea and sky. Outside, the grounds are meticulously landscaped with mature plantings, sprawling lawns, and specimen trees that create an exceptional sense of privacy. There is ample room for an in-ground pool in multiple locations, as well as significant opportunity for future expansion of the existing residence should additional space be desired. For those seeking that quintessential beachfront North Fork home without sacrificing the convenience of boating on the Peconic Bay, 920 Cedar Point E represents a truly exceptional offering.

920 Cedar Point Drive E, Southold
$1,549,999
4 Beds ⋅ 4 Baths ⋅ 998241 MLS
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. New, New New, Priced to Sell. Present all offers, seller negotiable.

3715 Hortons Lane, Southold
$3,695,000
3 Beds ⋅ 4 Baths ⋅ 997738 MLS
Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision. The grounds are equally compelling. A tennis court is already in place, and the oversized detached three-car garage adds flexibility for storage, studio space, or future accessory use, leaving ample room to site a pool. Centrally located with easy access to the North Fork’s vineyards, farm stands, restaurants, and marinas, the setting strikes a balance between privacy and convenience. Offerings with this combination of land, beach quality, and potential are increasingly rare, presenting a clear opportunity to create a premier waterfront compound.

1480 Old Wood Path, Southold
$3,450,000
5 Beds ⋅ 4 Baths ⋅ 995842 MLS
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.

790 N Sea Drive, Southold
$1,149,999
3 Beds ⋅ 2 Baths ⋅ 991901 MLS
Welcome to this One-of-a-Kind 3-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.

52755 Soundview Avenue, Southold
$2,250,000
4 Beds ⋅ 5 Baths ⋅ 990099 MLS
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.

1665 Glenn Road, Southold
$949,000
4 Beds ⋅ 3 Baths ⋅ 982950 MLS
Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen with new refrigerator, and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage with brand new doors, and a full basement with 8-foot ceilings offering excellent storage and a new hot water heater, gas heat, and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is in the Founders Park and Beach Park District, with direct access to a sugar sand beach, park and playground and is just moments from wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

240 Lisa Drive, Southold
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 973460 MLS
Build your dream home on this exceptional waterfront lot offering unobstructed, forever views and breathtaking sunsets over the pristine waters of the sound. With plans already in place, you can break ground on your custom home without delay. Nestled in one of the most sought-after locations on the North Fork, this property offers the perfect blend of privacy and convenience—just minutes from local vineyards, farm stands, dining, beaches, and marinas. Set in a serene and scenic location, this property offers direct access to miles of beach for peaceful walks along the shore, and is just moments from the tranquil Goldsmith Inlet, perfect for kayaking, paddleboarding, or simply enjoying nature at its finest. Whether you’re looking for a peaceful weekend retreat or a full-time coastal haven, this rare opportunity delivers it all. A one-of-a-kind acre-and-a-half property situated on a 40-foot-high bluff above the Long Island Sound, with clear views of the Connecticut shoreline and gorgeous northwest sunsets! Hidden off North Road (County Road 48) in Peconic, access is via a mile-long private road. This is the final piece of a six-lot subdivision. Delivering a powerful feeling of privacy, in a totally natural setting! Truly a MUST SEE for the individual searching for solitude, privacy, and relaxation! Full Building Permits Approved. Price listed is for vacant lot only including permits to build, which can be modified. Come see this extraordinary location and design your dream home! This listing may include images that have been digitally altered or virtually staged.

4760 Blue Horizon Bluffs, Peconic
$850,000
3 Beds ⋅ 4 Baths ⋅ 985489 MLS
Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and the charming village of Southold, with its shops, waterfront, and access to the Long Island Sound. The land at 150 Baywater Avenue is tied to the remarkable story of Maltby Freeman, a formerly enslaved man who earned his freedom in 1807 and, through extraordinary determination, came to own this very property along Bayview near South Harbor Road. Maltby and his wife, Dorcus Benjamin, began with a single-room structure, gradually expanding it into a family homestead in the early 1800s. Their descendants continued to acquire land, eventually owning a house and 30 acres. The Freeman family’s story is one of the earliest documented examples of Black land ownership and upward mobility on Long Island, and this property stands as a tangible connection to that chapter of American history. The property is offered strictly as-is, presenting a rare opportunity for a developer, preservationist, or visionary owner-builder. Included in the sale is a complete set of fully approved architectural and construction plans, a process that required two years of review by the Historic Preservation Commission, Town Planning Department, and Building Department. This extensive approval represents significant time, cost, and expertise that the next owner will not need to replicate. With permits and plans already secured, construction can begin immediately upon closing. For those seeking a property defined by history, character, and forward potential, 150 Baywater Avenue is ready for its next chapter.

150 Baywater Avenue, Southold
$1,799,000
4 Beds ⋅ 3 Baths ⋅ 983217 MLS
Private, polished, and distinctly North Fork, this designer's own Nantucket-style home offers generous spaces and exceptional privacy at the end of a long drive near historic Horton’s Point Lighthouse. Set on nearly an acre of mature landscaping, a wide mahogany porch opens to a dramatic foyer and expansive, light-filled living area with custom moldings, French doors to patio and plantation shutters. The heart of the home is the spacious, sun-filled kitchen and breakfast room, where Carrera marble counters, an oversized island and French doors to the deck and patio create an easy flow from morning coffee to summer entertaining. The adjoining formal dining room offers a more traditional setting when the occasion calls for it. The main-level primary suite, with high ceiling, wide oak floors, large closet and renovated bath with soaking tub and Carrera-tiled shower, makes first-floor living effortless. An office/library, powder room and laundry complete the main level. Upstairs, an airy loft leads to three spacious bedrooms and a full bath, creating comfortable separation for guests. In the rear yard, an expansive exotic-wood deck with pergola, stone patio and fire-pit area overlook a fully fenced lawn and established gardens with mature hydrangeas, crepe myrtle, raised vegetable beds and evergreen screening, with room for a pool. The detached two-car garage with additional storage connects by covered portico. Close to LI Sound beaches, Southold and Greenport Villages, wineries, farm stands and local 5-star restaurants.

25 Lighthouse Road, Southold
$950,000
3 Beds ⋅ 2 Baths ⋅ 964309 MLS
Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private escape that backs directly onto protected woodlands. One of the home’s standout features is an expansive four-season sunroom, which serves as a light-filled bridge between the indoors and your own quiet backyard sanctuary. Whether you are hosting a summer brunch or enjoying a morning coffee, the surrounding nature ensures a level of privacy that is truly rare. Additionally, the backyard features ample room for a pool, complete with an already approved pool permit to fast-track your summer dreams. Inside, the residence is designed for effortless living and is flooded with natural light. The main level offers the ultimate convenience of a primary bedroom with an ensuite bath and a dedicated laundry room, anchored by a spacious living area perfect for relaxing. Upstairs, you will find two additional oversized bedrooms—one featuring a generous walk-in closet—along with easy access to the attic. Modern essentials are seamlessly integrated throughout, including a full-house generator for peace of mind, a zoned irrigation sprinkler system, and a built-in Sonos system to set the mood for any occasion. This property places the very best of the North Fork right at your fingertips, situated just minutes from the stunning waters of Goose Creek, the sands of Cedar Beach, and Southold’s vibrant main street known for boutique shopping and fine dining. With renowned farmstands and vineyards only a short drive away, this home represents a rare opportunity to enjoy a secluded coastal lifestyle in one of the area’s most sought-after locations.

5845 N Bayview Road, Southold
$1,445,000
3 Beds ⋅ 2 Baths ⋅ 975344 MLS
Boaters Dream! Located in Southold, this 3-bedroom, 2-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen includes modern appliances and ample counter space. Large windows provide natural light and water views, with direct access to the rear deck. The outdoor space includes a spacious deck with room for seating and dining, along with a gas grill setup. The dock provides convenient access for boating, kayaking, and other activities. The home includes three bedrooms and two bathrooms, offering flexible space for a variety of living arrangements. Additional features include well-maintained interiors and updated elements throughout. Conveniently located near local wineries, restaurants, and shops, with access to all that the North Fork has to offer.

470 Windy Point Lane, Southold
$2,295,000
4 Beds ⋅ 3 Baths ⋅ 976743 MLS
Rare 1.07-Acre Coastal Compound on The Strand Set along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach "non-buildable" parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

875 & 785 The Strand, East Marion
$999,000
3 Beds ⋅ 2 Baths ⋅ 957993 MLS
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.

3475 Oaklawn Avenue, Southold
$1,550,000
4 Beds ⋅ 4 Baths ⋅ 953464 MLS
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. New Construction Package – $1,550,000 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, 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. 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. The North Fork is Calling Your Name!

500 Summer Lane, Southold
$6,850,000
5 Beds ⋅ 5 Baths ⋅ 946886 MLS
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, 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.

1750 Hobart Road, Southold
$2,399,000
3 Beds ⋅ 2 Baths ⋅ 943087 MLS
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 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!!!

470 Goose Creek Lane, Southold
$2,495,000
3 Beds ⋅ 2 Baths ⋅ 932327 MLS
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.

1455 Cedar Point Drive, Southold
$3,695,000
6 Beds ⋅ 4 Baths ⋅ 928708 MLS
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.

105 Waterview Drive, Southold
$1,499,000
3 Beds ⋅ 4 Baths ⋅ 924424 MLS
Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, 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: 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 and breezeway. 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 and 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. Option 2: Purchase As-Is with Approved Plans – $1,499,000 Prefer to build on your own schedule or with your own team? The existing home is also available as-is . 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 one of the North Fork’s most prestigious waterfront streets — just steps to a private beach and directly across from a scenic vineyard.

535 Bay Home Road, Southold
$2,500,000
5 Beds ⋅ 5 Baths ⋅ 903844 MLS
Welcome to the epitome of elegance and comfort at 3470 N Bayview Rd, Southold NY. This high-quality 5-bedroom, 5-bathroom home is located just a stone's throw away from the popular Goose Creek Beach. The spacious horseshoe driveway and 2-car garage ensure ample parking and easy access. Step inside to be greeted by high ceilings and an open floor plan, allowing for a seamless flow throughout the main level. The kitchen is designed to keep you connected with your guests. Whether you're preparing a meal or pouring a drink, you can easily engage with your visitors in the dining room or the living room. The first floor features two en suite bedrooms, a laundry room, and a half bath. The second floor offers a third en suite bedroom, two additional bedrooms, a full bathroom, and a loft area perfect for a home office. Outdoors, the home boasts a backyard oasis complete with an in-ground pool, lush gardens, and a basketball court. Choose to relax on the front porch or the private back deck and patio. Nestled in a vibrant community with local amenities, this home is more than just a place to live – it's a lifestyle. Experience the luxury and tranquility of this North Fork sanctuary.

3470 N Bayview Road, Southold
$2,995,000
4 Beds ⋅ 6 Baths ⋅ 906322 MLS
Southold Stunner- New Construction This one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven, Thermador wine fridge, twin Cove dishwashers, plus Scotsman ice maker for those "bring on summer" gatherings. Quartz counters and designer finishes keep it fresh and timeless. Head downstairs: a finished lower level with a private movie theater and plenty of space. Outside, it's pure Zen mode with a 20x40 custom heated saltwater Gunite pool, extended 24x48 porcelain patio for easy entertaining, and a fire pit zone ready for end-of-day stories under the stars. If "flawless, never lived in, fully loaded by the beach" is your thing, this delivers - all the luxury, none of the pretense. Could be you! * Additional Details Include: Laundry room on first floor, additional washer/dryer on second floor, Floors 3 quarter inch Red Oak 7 inch wide hardwood flooring, Custom Wellwood European Style Cabinets, Propane forced air, Red cedar shake 5/8, No HOA, Propane fireplace, 400 Amp Electric Service, Appliances - 48 inch Sub Zero Refrigerator/Freezer, 48 inch Wolf Gas Range, 30 inch Wolf Wall Oven, 30 inch Wolf Microwave Oven, Scottsman Ice Maker, 24 inch Cobe Dishwashers, 24 inch Thermador Built in Wine Fridge, Quartz Countertops, Patio Stone and Size 24 by 48 Porcelain Patio Pavers, Pool Specs - 20 by 40 Custom Gunite Pool, Propane Pool Heater, 3 -Lennox 14 seer systems, Merit series air handlers and condensers, 5 zones total, Aprilaire 2210 merv, 16 media filters, Honeywell T6 WiFi thermostats installed on all zones, Healthy climate ERV installed in attic connected to 2nd floor system for fresh air.

80 Deer Run, Southold
$2,875,000
4 Beds ⋅ 5 Baths ⋅ 893733 MLS
NEW WATERFRONT CONSTRUCTION Thoughtfully crafted and beautifully finished, this 4-bedroom, 5-bath custom waterfront home offers over 2,900 sq ft of elevated living space — a seamless blend of modern luxury and timeless coastal charm. Set in a peaceful, private location, it showcases stunning panoramic water views from nearly every room and effortless indoor-outdoor flow designed to embrace the natural surroundings and relaxed beach lifestyle. HIGHLIGHTS...4 spacious en suite bedrooms....5 bathrooms...2 light-filled living areas perfect for lounging or entertaining....Custom white oak cabinetry, vanities, and detailed millwork....White oak flooring throughout..... Chef’s kitchen....Sub-Zero refrigerator and wine fridge....Wolf stove....Sleek Dekton countertops....Expansive glass doors that open the kitchen to the outdoor living space with direct water views — perfect for hosting or unwinding by the shore....Second-floor outdoor lounge terrace overlooking the water....Separate garage with finished loft....Mahogany fencing....Professionally landscaped grounds. Located just minutes from the area’s best beaches, this brand-new waterfront home offers the ultimate combination of high-end design, natural beauty, and relaxed luxury living. The photos are virtually staged.

6370 Skunk Lane, Cutchogue
$2,799,000
8 Beds ⋅ 7 Baths ⋅ 859020 MLS
2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom estate, offering the rare opportunity to personalize your dream home to suit your lifestyle and taste. Whether your envisioning a peaceful year-round residence, a high-end vacation home or a lucrative investment property, this home offers it all. Your luxury escape awaits -custom build your forever home today! Photos shown are from an identical recently built house In Southold --- Easy To Preview.

1350 Hortons Lane, Southold
$1,249,000
3 Beds ⋅ 2 Baths ⋅ L3590177 MLS
Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the 'tower' of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!

2055 Boisseau Avenue, Southold

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