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$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
$1,199,999
3 Beds ⋅ 2 Baths ⋅ 991901 MLS
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.

52755 Soundview Avenue, Southold
$895,000
3 Beds ⋅ 3 Baths ⋅ 995779 MLS
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.

445 Budds Pond Road, 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
$1,239,999
4 Beds ⋅ 4 Baths ⋅ 988709 MLS
Tucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath residence offers the perfect blend of modern construction, thoughtful design, and effortless North Fork charm. From the moment you arrive, the inviting front porch, complete with a classic swing, sets the tone for relaxed living. Inside, the home is thoughtfully designed with a seamless flow, anchored by a stunning, light-filled chef’s kitchen that truly serves as the heart of the home. Featuring a large center island with seating, quartz countertops, custom cabinetry, stainless steel appliances, and designer pendant lighting, the space is both functional and refined. Expansive windows bring in natural light and tranquil views, while the kitchen opens effortlessly into a beautifully appointed dining area that is bright and welcoming and leads directly to the outdoor deck, creating a seamless indoor-outdoor lifestyle. This home offers a rare and highly desirable layout with primary bedrooms on both the first and second floors, each with en-suite bathrooms. The second-floor primary suite is particularly impressive, featuring a walk-in closet and a spacious bath complete with a large shower and double vanity sinks. Throughout the home, crown molding and 9-foot ceilings on the first floor enhance the sense of scale and craftsmanship, while an open-to-above foyer adds volume and an airy, inviting feel. All bedrooms are generously sized and feature large windows, filling each space with natural light. Guest and additional bathrooms are well-appointed with oversized tubs and showers, offering comfort and convenience throughout. Additional living space is found in the cozy, full glass sunroom, which opens to a large, spacious deck overlooking a completely private backyard. Designed for both relaxation and entertaining, the outdoor space includes a large 8-person hot tub (just 2 years old), lush landscaping, and a charming garden room—perfect as a lounge, studio, or quiet retreat. The entire property is fenced and includes a dedicated dog run area. A partially finished basement provides excellent flexible space with a walk-in closet, ideal for a home gym or media room. And the location? Truly exceptional. Just moments from Kenny’s Beach, renowned for its expansive beach and stunning sunsets. A rare opportunity to own a nearly new home with exceptional features, flexible living space, and an unbeatable location—where every detail has been thoughtfully considered.

75 Birch Road, Southold
$3,899,000
992332 MLS
Some estates are acquired. The exceptional are entrusted to the next chapter. Set within the North Fork’s most storied agricultural landscape, this extraordinary lifestyle farm unfolds across protected vineyard acreage and open sky - a private world defined by refinement, scale, and possibility. Being offered together are two parcels: 43.7 preserved acres, where development rights have been sold to safeguard the integrity of the land, and a separate 1.84-acre parcel with development rights intact. The result is both permanence and potential -protected beauty paired with the opportunity to create something entirely your own. Twenty-five acres of mature vines - Merlot, Cabernet Franc, Chardonnay, Sauvignon Blanc, and Pinot Blanc - stretch in disciplined rows across the landscape. Three acres of Dwarf Tall Spindle apples flourish alongside more than 200 peach and nectarine trees, complemented by berries and cultivated vegetables. The plantings are established. The soil is proven. The setting is timeless. A 3,600-square-foot Morton building with refrigeration anchors the farm’s operations, housing equipment that is included in the offering. The infrastructure is in place for continued vineyard production, expanded agricultural pursuits, or a refined farm-to-table vision executed at the highest level. The cleared and level 1.84-acre residential parcel invites the creation of a bespoke estate residence - perhaps with pool and terraces overlooking the vines - designed with intention, privacy, and architectural distinction. Here, mornings begin with light rising over the vineyard rows. Evenings settle into quiet horizon views. The landscape itself becomes both backdrop and legacy. Positioned within the North Fork’s celebrated wine and agricultural corridor - yet moments from acclaimed dining, marinas, beaches, and charming villages - this is a rare convergence of pastoral serenity and cultivated lifestyle. Impeccably maintained and deeply rooted, this offering is not merely land. It is a long-view investment in beauty, heritage, and possibility - awaiting its next discerning custodian.

46975 Main Road, Southold
$2,895,000
5 Beds ⋅ 6 Baths ⋅ 990263 MLS
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.

1135 Wildberry Lane, Southold
$1,799,000
992553 MLS
Calling all builders and investors! Beautiful 8.65 acres of cleared, leveled land in Southold Town. This parcel is zoned R-80, (2 Acre zoning) and has 250' of frontage on Sound Avenue (North Road) and access from adjacent Leon Road. Sellers will not consider offers "subject to" any permits or approvals.

420 Leon 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!

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
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 983217 MLS
Tucked at the end of a long, private drive on one of Southold’s historic streets, this custom-built, designer's own Nantucket-style home delivers 3,800 square feet of luxury on just under an acre of manicured gardens. Minutes from both the Sound and Peconic Bay, plus the restaurants, wineries, and village charm that make North Fork living feel like a permanent vacation. Step onto the mahogany porch, and the vibe hits immediately. Inside, a dramatic two-story foyer flows into an inviting light-filled living room. The oversized, well-appointed kitchen is an entertainer's delight with Carrera marble countertops and huge island with seating for 5. Dinner parties? Handled. The adjacent formal dining room is ready when the guest list grows. Main-level primary suite with soaking tub, Carrera-tiled shower, and walk-in closet is a romantic escape. There is also a main level laundry room, guest bath, and library/office. Upstairs, a loft adds natural light and a space to sit and read or relax, and 3 additional oversized bedrooms that offer everyone a private space. The yard is outdoor living at its finest. Stone patio, sprawling exotic wood deck with pergola, and a fire pit lounge make for late-night conversations in the lush, thoughtfully designed yard (which has plenty of space for a pool!). The detached two-car garage gives you room to grow. Polished yet comfortable. Private yet not remote. A true North Fork experience for all seasons.

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
$949,000
3 Beds ⋅ 2 Baths ⋅ 975848 MLS
North Fork Coastal Living by the Sound. Located in Peconic near Goldsmith Inlet and the Long Island Sound, this house was personally built by the owner, an experienced home builder, with a focus on superior materials, meticulous construction and pride of ownership. An open living, dining, and kitchen areas extend to a balcony that showcases beautiful sunsets and water views, creating a seamless indoor-outdoor experience. Currently unfurnished and ready for your own personal touch! Nearby beach is a stones throw from the house, and Goldsmith’s inlet provide opportunities for kayaking, paddle boarding, swimming and fishing while vineyards, farm-to-table restaurants, and local landmarks such as Horton Point Lighthouse are just minutes away. With endless outdoor recreation and breathtaking evening skies, this property captures the best of North Fork living.

155 2nd Avenue, Peconic
$1,545,000
4 Beds ⋅ 3 Baths ⋅ 975549 MLS
Coastal Living, Without the Crowds Set along one of East Marion's most coveted waterfront stretches, 785 The Strand offers a rare blend of privacy, natural beauty, and effortless coastal living. Experience quiet luxury with direct beach access-without the crowds. Perched above the shoreline and directly across from the Long Island Sound, this thoughtfully designed residence captures the understated elegance of the North Fork lifestyle. Surrounded by mature landscaping and sited to take full advantage of its coastal setting, the .56-acre property features a light-filled, two-story home with five bedrooms and four baths, complemented by an oversized pool, two fireplaces, and multiple outdoor spaces designed for both entertaining and relaxation. Open, airy, and filled with natural light, the home is designed to maximize comfort and connection to its surroundings, which include protected Pebble Beach-communally-owned "no development" lots to the east and south. Expansive windows frame the landscape, while clean architectural lines and warm finishes create a refined yet relaxed atmosphere. Here, beach access is part of everyday life, not an occasion. Also ideally located near marinas, farm stands, wineries, golf courses, and a short drive to Greenport Village. This is a rare opportunity to own in one of the North Fork's most desirable and tightly held locations.

785 The Strand, East Marion
$1,099,000
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 – $1,400,000 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, 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
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 951805 MLS
Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 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. Lastly, the final photos on this listing demonstrate the secret hatch in the floor and each person to visit between 1750-1800's carved their names into the china cabinet paneling. So interesting to explore all the names. ** 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.**

3500 Pine Neck Road, 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 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.

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
$499,000
931612 MLS
.38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary work has been done with the DOH, Planning Board, or building dept at this time. Please don't walk property without your agent present.

11195 N Bayview Road, 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
$2,250,000
914178 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, very wooded setting! Truly a MUST SEE for the individual searching for solitude, privacy, and relaxation! Board of Health Permit is issued. Building Permit is issued...all are included!

4760 Blue Horizon Bluffs, Peconic
$3,295,000
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
$4,900,000
896328 MLS
Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres, the property includes a 4.46-acre winery parcel with development rights intact and an additional 46.36 acres of vineyard with 34.5 acres under vine. The estate features approximately 19,500 square feet across three primary buildings, including a beautifully appointed tasting room with seating for more than sixty guests, cocktail capacity exceeding one hundred, and an expansive outdoor patio overlooking the vines. The winery itself houses a temperature-controlled production facility with fermentation cellar, bottling line, and laboratory, while the barrel and storage building provides over 8,000 square feet of climate-controlled space for aging and inventory. The setting is as breathtaking as it is functional, with panoramic vineyard views, manicured lawns, and a blend of rustic charm and refined elegance that makes the property a sought-after destination for wine enthusiasts, weddings, corporate events, and private celebrations. Outdoor features include a pergola-covered patio bar, gazebo, and multiple gathering spaces designed to enhance the guest experience. The sale includes the Osprey’s Dominion brand, extensive winemaking and agricultural equipment, and existing inventory, ensuring a seamless transition for a new owner. With a loyal customer base, a wine club of hundreds of members, and a certified sustainable harvest underway, the vineyard is positioned for continued success. This is a rare chance to acquire a turnkey winery in one of New York’s most vibrant wine regions. Whether you are an experienced vintner or an investor seeking a marquee North Fork asset, Osprey’s Dominion offers unmatched prestige, proven operations, and boundless potential.

44075 Route 25, Peconic

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