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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.

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

$4,299,000

WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond, plus community boating rights with access to the residents’ boat basin, the property offers exceptional privacy without sacrificing comfort or convenience. Custom built in 1993, the approximately 3,500-square-foot residence offers four bedrooms, three full baths and three levels designed for gracious year-round living. Bold proportions, soaring 20-foot ceilings, walls of glass and a sweeping staircase capture the confident glamour of grand-scale coastal architecture, while abundant natural light and extraordinary water views give the interiors a timeless quality. This is not a conventional beach house; it is a substantial bayfront residence designed to make an impression. The dramatic double-height great room is anchored by a rare natural coral-stone fireplace and opens to more than 1,500 square feet of exterior decking—an exceptional setting for entertaining, dining outdoors or simply watching the light move across the bay. A formal waterside dining room complements the spacious eat-in kitchen, which provides generous counter space and an inviting place for everyday gatherings. The main level also includes pantry and laundry areas, together with a flexible 4th bedroom or den and adjacent full bath—ideal for guests, a private home office or convenient first-floor living. Ascend the sweeping staircase to the waterfront primary suite, a private retreat featuring magnificent bay views, its own waterside terrace, a luxurious full bath and walk-in closet. Two additional bedrooms and another full bath complete the upper level. The finished lower level expands the home’s recreational possibilities with a game or media area, direct access to a waterside terrace and an attached multicar garage. Outside, the expansive, level grounds provide ample room for entertaining, recreation and quiet enjoyment amid beautiful natural surroundings. A private boardwalk leads directly to the sandy beach, where days can be spent swimming, fishing, kayaking, paddleboarding or launching a morning adventure on the bay. Although wonderfully private, the estate is only minutes from Southold Village and the restaurants, vineyards, farm stands, shops, beaches and boating destinations that define North Fork living. Additional amenities include public water, a supplemental well, oil-fired forced-air heat and central air conditioning. Rare acreage, substantial private beach frontage, community boating access and a dramatic waterfront residence come together in one extraordinary Southold offering. Paradise Found.

4 Beds ⋅ 3 Baths ⋅ 1053616 MLS

WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond, plus community boating rights with access to the residents’ boat basin, the property offers exceptional privacy without sacrificing comfort or convenience. Custom built in 1993, the approximately 3,500-square-foot residence offers four bedrooms, three full baths and three levels designed for gracious year-round living. Bold proportions, soaring 20-foot ceilings, walls of glass and a sweeping staircase capture the confident glamour of grand-scale coastal architecture, while abundant natural light and extraordinary water views give the interiors a timeless quality. This is not a conventional beach house; it is a substantial bayfront residence designed to make an impression. The dramatic double-height great room is anchored by a rare natural coral-stone fireplace and opens to more than 1,500 square feet of exterior decking—an exceptional setting for entertaining, dining outdoors or simply watching the light move across the bay. A formal waterside dining room complements the spacious eat-in kitchen, which provides generous counter space and an inviting place for everyday gatherings. The main level also includes pantry and laundry areas, together with a flexible 4th bedroom or den and adjacent full bath—ideal for guests, a private home office or convenient first-floor living. Ascend the sweeping staircase to the waterfront primary suite, a private retreat featuring magnificent bay views, its own waterside terrace, a luxurious full bath and walk-in closet. Two additional bedrooms and another full bath complete the upper level. The finished lower level expands the home’s recreational possibilities with a game or media area, direct access to a waterside terrace and an attached multicar garage. Outside, the expansive, level grounds provide ample room for entertaining, recreation and quiet enjoyment amid beautiful natural surroundings. A private boardwalk leads directly to the sandy beach, where days can be spent swimming, fishing, kayaking, paddleboarding or launching a morning adventure on the bay. Although wonderfully private, the estate is only minutes from Southold Village and the restaurants, vineyards, farm stands, shops, beaches and boating destinations that define North Fork living. Additional amenities include public water, a supplemental well, oil-fired forced-air heat and central air conditioning. Rare acreage, substantial private beach frontage, community boating access and a dramatic waterfront residence come together in one extraordinary Southold offering. Paradise Found.

3525 Paradise Point Road, Southold

$3,899,000

A rare opportunity to create a truly bespoke North Fork lifestyle or equestrian estate in the heart of Southold’s celebrated agricultural landscape. Privately set across 45.54 acres, the offering includes 43.7 acres of preserved agricultural land and a separate 1.84-acre residential parcel with development rights intact-an exceptional setting to create a distinctive residence overlooking your own vineyard, with expansive acreage offering tremendous potential for horses and equestrian pursuits. Twenty-five acres of mature vines are complemented by apple, peach and nectarine orchards, berries, and cultivated vegetables, with irrigation and agricultural equipment included. A meticulously maintained 3,600-square-foot Morton building with refrigeration provides valuable infrastructure and potential flexibility for agricultural or equestrian use. Completely secluded, with sweeping pastoral views and beautiful sunsets, this extraordinary property offers the rare freedom to ride, cultivate, entertain, and create a private farm-to-table country lifestyle entirely your own.

992332 MLS

A rare opportunity to create a truly bespoke North Fork lifestyle or equestrian estate in the heart of Southold’s celebrated agricultural landscape. Privately set across 45.54 acres, the offering includes 43.7 acres of preserved agricultural land and a separate 1.84-acre residential parcel with development rights intact-an exceptional setting to create a distinctive residence overlooking your own vineyard, with expansive acreage offering tremendous potential for horses and equestrian pursuits. Twenty-five acres of mature vines are complemented by apple, peach and nectarine orchards, berries, and cultivated vegetables, with irrigation and agricultural equipment included. A meticulously maintained 3,600-square-foot Morton building with refrigeration provides valuable infrastructure and potential flexibility for agricultural or equestrian use. Completely secluded, with sweeping pastoral views and beautiful sunsets, this extraordinary property offers the rare freedom to ride, cultivate, entertain, and create a private farm-to-table country lifestyle entirely your own.

46975 Main Road, Southold

$3,695,000

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.

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

$3,675,000

Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. 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, additional bedrooms 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.

5 Beds ⋅ 6 Baths ⋅ 1031351 MLS

Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. 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, additional bedrooms 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.

150 Deer Run, Southold

$3,450,000

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.

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

$3,095,000

Ready to Move In -- New Construction Luxury Southold Home completed October 2026. Interior photos coming 10/11/26. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with peaceful North Fork country living. Features 5,100+ SF of living space on 3 levels with 4 Bedrooms and 4.5 Bathrooms plus a bonus room/office over your attached 3 car garage. This stunning home has everything including a Giant front wrap-around-porch, heated saltwater 18x36 pool, and both first and second level primary bedrooms with ensuite baths and walk-in-closets. All high-end finishes were used throughout including Natural Alaskan Cedar Siding, Anderson 400 Series Windows, Luxury Appliances and Quartz Countertops, Wide Plank Natural White Oak Floors, Gas Fireplace, Custom Glass Shower Doors throughout, and more. Full Finished Basement with 9.5’ ceilings, Outside entrance to the lower level, full lower level bathroom, built in wine fridge, and luxury oversized double glass doors leading to your Gym and Custom Cedar Sauna. Equipped with the latest smart home technology including Hard Wired Ring Camera System, 5 Zone Sonos Sound System, Hard Wired EERO wifi access points, Lutron Smart Lighting, Wifi Pool Equipment, Wifi Sprinkler control, and more. Enjoy exclusive Southold Park District rights—offering access to private beaches, kayak launches, and Founders Landing—while being just minutes from stunning Long Island Sound beaches, scenic Sound View Dunes, world-class vineyards, farm stands, and charming village dining.

4 Beds ⋅ 5 Baths ⋅ 1039113 MLS

Ready to Move In -- New Construction Luxury Southold Home completed October 2026. Interior photos coming 10/11/26. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with peaceful North Fork country living. Features 5,100+ SF of living space on 3 levels with 4 Bedrooms and 4.5 Bathrooms plus a bonus room/office over your attached 3 car garage. This stunning home has everything including a Giant front wrap-around-porch, heated saltwater 18x36 pool, and both first and second level primary bedrooms with ensuite baths and walk-in-closets. All high-end finishes were used throughout including Natural Alaskan Cedar Siding, Anderson 400 Series Windows, Luxury Appliances and Quartz Countertops, Wide Plank Natural White Oak Floors, Gas Fireplace, Custom Glass Shower Doors throughout, and more. Full Finished Basement with 9.5’ ceilings, Outside entrance to the lower level, full lower level bathroom, built in wine fridge, and luxury oversized double glass doors leading to your Gym and Custom Cedar Sauna. Equipped with the latest smart home technology including Hard Wired Ring Camera System, 5 Zone Sonos Sound System, Hard Wired EERO wifi access points, Lutron Smart Lighting, Wifi Pool Equipment, Wifi Sprinkler control, and more. Enjoy exclusive Southold Park District rights—offering access to private beaches, kayak launches, and Founders Landing—while being just minutes from stunning Long Island Sound beaches, scenic Sound View Dunes, world-class vineyards, farm stands, and charming village dining.

390 Wildberry Lane, Southold

$2,999,000

Once operated as a bed and breakfast, this distinctive property sits on 11.31 private acres, including 9.31 acres of open space and 2-acres of buildable space in one of Southold's most prestigious enclaves. Offering exceptional versatility and income potential, the property features a serving kitchen, dining room, library, five fireplaces, tile flooring throughout, and a four-car garage with a basement featuring 10-foot ceilings. An irrigation system and two-stall barn add to the appeal. A rare combination of privacy, space, and opportunity, ideal for horses, gardens, a potential income-producing venture, or future development.

4 Beds ⋅ 6 Baths ⋅ 1052436 MLS

Once operated as a bed and breakfast, this distinctive property sits on 11.31 private acres, including 9.31 acres of open space and 2-acres of buildable space in one of Southold's most prestigious enclaves. Offering exceptional versatility and income potential, the property features a serving kitchen, dining room, library, five fireplaces, tile flooring throughout, and a four-car garage with a basement featuring 10-foot ceilings. An irrigation system and two-stall barn add to the appeal. A rare combination of privacy, space, and opportunity, ideal for horses, gardens, a potential income-producing venture, or future development.

9680 N Bayview Road, Southold

$2,995,000

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.

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

$2,950,000

Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location. Held in the same family for more than 50 years, the over 4000-square-foot home is set on two private acres overlooking the natural beauty of Great Pond. Expansive light-filled rooms, walls of glass and bold architectural lines create a residence that feels as compelling today as it was when first conceived. Mature landscaping, an inground pool, abundant wildlife and magnificent sunsets all contribute to the architectural composition. These features enhance the sense of retreat and home, while two beautiful Long Island Sound beaches—Kenney’s and McCabe’s—are just moments away. A true North Fork treasure, equal parts architectural time capsule and North Fork, grab this opportunity before it's gone.

4 Beds ⋅ 4 Baths ⋅ 963793 MLS

Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location. Held in the same family for more than 50 years, the over 4000-square-foot home is set on two private acres overlooking the natural beauty of Great Pond. Expansive light-filled rooms, walls of glass and bold architectural lines create a residence that feels as compelling today as it was when first conceived. Mature landscaping, an inground pool, abundant wildlife and magnificent sunsets all contribute to the architectural composition. These features enhance the sense of retreat and home, while two beautiful Long Island Sound beaches—Kenney’s and McCabe’s—are just moments away. A true North Fork treasure, equal parts architectural time capsule and North Fork, grab this opportunity before it's gone.

9305 Soundview Avenue, Southold

$2,899,000

Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed living space, plus a finished 1,166-square-foot lower level. Sun-drenched interiors showcase wide-plank wire-brushed white oak flooring, custom millwork and cabinetry, Restoration Hardware lighting, recessed lighting, and Sonos sound throughout both the home and outdoor entertaining spaces. Every room in the home captures stunning water views, creating a seamless connection to the surrounding waterfront setting. The spectacular gourmet kitchen is designed for both everyday living and entertaining, featuring a Sub-Zero refrigerator, Wolf gas cooktop and double ovens, quartz and Caesarstone countertops, oversized center island, Bosch and Fisher & Paykel dishwashers, and a stunning butler’s pantry accented with Cle Tile backsplash. The living room is equally impressive with a custom wood-burning fireplace, built-in cabinetry, and an elegant wet bar complete with Sub-Zero beverage refrigerator, wine refrigerator, ice machine, and designer finishes throughout. The fully finished lower level offers exceptional additional living space with a kitchenette, double egress windows, and Fujitsu mini-split system—ideal for guests, recreation, or extended entertaining. Upstairs, four spacious water-view bedrooms include a luxurious primary suite featuring cathedral planked ceilings, a handmade vintage wood mantel, private deck access, walk-in closet, and spa-inspired bath. Elegant lime-washed walls add warmth and character to every bathroom. Outdoor living is nothing short of extraordinary with expansive first and second floor decking, a rooftop deck with panoramic water views, premium IPE Brazilian hardwood decking, covered outdoor entertaining area with built-in heaters and ceiling fans, outdoor shower, wired railings, cedar shake siding, Andersen 400 Series windows and doors, and beautifully landscaped grounds surrounded by mature privacy hedges. A true boater’s paradise, the property accommodates a large boat and offers direct access to Peconic Bay, Shinnecock Bay, and nearby sandbars for boating, kayaking, paddleboarding, clamming, and enjoying the ultimate North Fork waterfront lifestyle.

4 Beds ⋅ 3 Baths ⋅ 1005049 MLS

Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed living space, plus a finished 1,166-square-foot lower level. Sun-drenched interiors showcase wide-plank wire-brushed white oak flooring, custom millwork and cabinetry, Restoration Hardware lighting, recessed lighting, and Sonos sound throughout both the home and outdoor entertaining spaces. Every room in the home captures stunning water views, creating a seamless connection to the surrounding waterfront setting. The spectacular gourmet kitchen is designed for both everyday living and entertaining, featuring a Sub-Zero refrigerator, Wolf gas cooktop and double ovens, quartz and Caesarstone countertops, oversized center island, Bosch and Fisher & Paykel dishwashers, and a stunning butler’s pantry accented with Cle Tile backsplash. The living room is equally impressive with a custom wood-burning fireplace, built-in cabinetry, and an elegant wet bar complete with Sub-Zero beverage refrigerator, wine refrigerator, ice machine, and designer finishes throughout. The fully finished lower level offers exceptional additional living space with a kitchenette, double egress windows, and Fujitsu mini-split system—ideal for guests, recreation, or extended entertaining. Upstairs, four spacious water-view bedrooms include a luxurious primary suite featuring cathedral planked ceilings, a handmade vintage wood mantel, private deck access, walk-in closet, and spa-inspired bath. Elegant lime-washed walls add warmth and character to every bathroom. Outdoor living is nothing short of extraordinary with expansive first and second floor decking, a rooftop deck with panoramic water views, premium IPE Brazilian hardwood decking, covered outdoor entertaining area with built-in heaters and ceiling fans, outdoor shower, wired railings, cedar shake siding, Andersen 400 Series windows and doors, and beautifully landscaped grounds surrounded by mature privacy hedges. A true boater’s paradise, the property accommodates a large boat and offers direct access to Peconic Bay, Shinnecock Bay, and nearby sandbars for boating, kayaking, paddleboarding, clamming, and enjoying the ultimate North Fork waterfront lifestyle.

405 Williamsburgh Drive, Southold

$2,895,000

North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, 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 spectacular 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 both as a private retreat while still 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 16x36, heated and surrounded by patio with outdoor kitchen the backyard is fully fenced in. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork.

5 Beds ⋅ 6 Baths ⋅ 1037213 MLS

North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, 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 spectacular 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 both as a private retreat while still 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 16x36, heated and surrounded by patio with outdoor kitchen the backyard is fully fenced in. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork.

1135 Wildberry Lane, Southold

$2,799,000

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.

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

$2,698,000

Bay Haven — 1430 Bay Haven Lane, Southold Classic coastal architecture meets contemporary North Fork living in this newly built custom residence set within the Bay Haven beach community, just three houses from the private community beach. Designed for effortless North Fork living, the home offers 3,035 square feet of living space, with four bedrooms and four full baths, complemented by approximately 3,340 additional square feet of garage, pool house, storage/art, and under-house utility and storage space. Inside, 10 foot first-floor ceilings, 9 foot second floor ceilings, natural hardwood floors, abundant natural light, custom millwork, built-ins, and site-built closets create a refined yet relaxed interior. Two primary suites, one on each floor, offer flexibility for year-round living and guests. Each features a walk-in closet, ensuite bath, and electric fireplace, while radiant-heated floors enhance the primary bath spaces. The first floor suite also includes a private office, while the second-floor suite enjoys seasonal bay views. At the heart of the home is a locally handcrafted kitchen with cabinetry extending to the 10 foot ceiling, a 48-inch professional style gas range beneath a custom arched hood, dual dishwashers, smart combination wall oven, farmhouse sink, pot filler, dual-zone wine refrigeration, and extensive custom storage. Indoor and outdoor living flow naturally through the three-season room, complete with custom cabinetry, TV hook up and fireplace, to the landscaped grounds and a heated pool. A poolside mudroom provides direct access to a full bath, shower, and changing area. The pool house adds another layer of entertaining space with a wine bar, dual zone wine refrigeration, and glass doors opening directly to the pool. The property extends well beyond the main residence with a detached garage and approximately 770 square foot second floor storage, ideally suited for an Art Space, plus approximately 1,800 square feet of under-house storage and utility space. Behind the design is a substantial infrastructure package: a high-efficiency five zone heat pump heating and cooling system, 3 zones of radiant heat, comprehensive spray foam insulation, a hybrid heat-pump water heater, three stage whole house filtration, controlled under-house dehumidification, energy efficient heat pump pool heating, smart pool control and lighting systems, Ring security, an I/A septic system, and 300-amp electrical service. Bay Haven combines privacy, craftsmanship and modern comforts with immediate access to the Bay. Cedar Beach is just 1.5 miles away, with the shops and restaurants of Southold nearby. Seasonal second floor bay views and year round glimpses of the water complete a home equally suited to summer escapes and year-round North Fork living.

4 Beds ⋅ 4 Baths ⋅ 1054890 MLS

Bay Haven — 1430 Bay Haven Lane, Southold Classic coastal architecture meets contemporary North Fork living in this newly built custom residence set within the Bay Haven beach community, just three houses from the private community beach. Designed for effortless North Fork living, the home offers 3,035 square feet of living space, with four bedrooms and four full baths, complemented by approximately 3,340 additional square feet of garage, pool house, storage/art, and under-house utility and storage space. Inside, 10 foot first-floor ceilings, 9 foot second floor ceilings, natural hardwood floors, abundant natural light, custom millwork, built-ins, and site-built closets create a refined yet relaxed interior. Two primary suites, one on each floor, offer flexibility for year-round living and guests. Each features a walk-in closet, ensuite bath, and electric fireplace, while radiant-heated floors enhance the primary bath spaces. The first floor suite also includes a private office, while the second-floor suite enjoys seasonal bay views. At the heart of the home is a locally handcrafted kitchen with cabinetry extending to the 10 foot ceiling, a 48-inch professional style gas range beneath a custom arched hood, dual dishwashers, smart combination wall oven, farmhouse sink, pot filler, dual-zone wine refrigeration, and extensive custom storage. Indoor and outdoor living flow naturally through the three-season room, complete with custom cabinetry, TV hook up and fireplace, to the landscaped grounds and a heated pool. A poolside mudroom provides direct access to a full bath, shower, and changing area. The pool house adds another layer of entertaining space with a wine bar, dual zone wine refrigeration, and glass doors opening directly to the pool. The property extends well beyond the main residence with a detached garage and approximately 770 square foot second floor storage, ideally suited for an Art Space, plus approximately 1,800 square feet of under-house storage and utility space. Behind the design is a substantial infrastructure package: a high-efficiency five zone heat pump heating and cooling system, 3 zones of radiant heat, comprehensive spray foam insulation, a hybrid heat-pump water heater, three stage whole house filtration, controlled under-house dehumidification, energy efficient heat pump pool heating, smart pool control and lighting systems, Ring security, an I/A septic system, and 300-amp electrical service. Bay Haven combines privacy, craftsmanship and modern comforts with immediate access to the Bay. Cedar Beach is just 1.5 miles away, with the shops and restaurants of Southold nearby. Seasonal second floor bay views and year round glimpses of the water complete a home equally suited to summer escapes and year-round North Fork living.

1430 Bay Haven Lane, Southold

$2,695,000

Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted for horses. While perfect as-is, its use could easily extend beyond equestrian purposes and be reimagined to suit your needs. A heated pool overlooking the vineyards rounds out the grounds, offering the perfect spot for entertaining or unwinding. Located less than a mile from bay beaches and the restaurants and shops of Southold Hamlet, putting amenities and everyday convenience equally within reach. This is a rare opportunity to own a classic North Fork property that balances open land, everyday comfort, and easy access to it all.

3 Beds ⋅ 2 Baths ⋅ 1036373 MLS

Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted for horses. While perfect as-is, its use could easily extend beyond equestrian purposes and be reimagined to suit your needs. A heated pool overlooking the vineyards rounds out the grounds, offering the perfect spot for entertaining or unwinding. Located less than a mile from bay beaches and the restaurants and shops of Southold Hamlet, putting amenities and everyday convenience equally within reach. This is a rare opportunity to own a classic North Fork property that balances open land, everyday comfort, and easy access to it all.

2850 Main Bayview Road, Southold

$2,695,000

This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and exceptional East End retreat Stunning carpentry, high-end appliances, and designer fixtures carry throughout. The custom-built kitchen features bespoke cabinetry and hardware, flowing seamlessly into a dining area and a light-filled living room anchored by a wood-burning fireplace. Oversized windows and a vaulted ceiling define the dining room, which connects to an oversized back deck overlooking the sprawling backyard. Outside, a gunite, heated, saltwater pool complements the cedar-shingled accessory structure, which combines a pool house with its own bathroom, a garage, a covered outdoor patio with a gas fireplace, and an outdoor shower. Back inside, two additional guest bedrooms share a full bath on the second floor, while downstairs, two large recreation rooms offer further customization and flexibility. The location is just as compelling as the house itself, minutes from Goose Creek Beach, Cedar Beach, Croteaux Vineyards, and the many shops and restaurants of Southold Hamlet. This is a special property with a real point of view that you'll look forward to walking into each time you return home.

5 Beds ⋅ 4 Baths ⋅ 1031524 MLS

This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and exceptional East End retreat Stunning carpentry, high-end appliances, and designer fixtures carry throughout. The custom-built kitchen features bespoke cabinetry and hardware, flowing seamlessly into a dining area and a light-filled living room anchored by a wood-burning fireplace. Oversized windows and a vaulted ceiling define the dining room, which connects to an oversized back deck overlooking the sprawling backyard. Outside, a gunite, heated, saltwater pool complements the cedar-shingled accessory structure, which combines a pool house with its own bathroom, a garage, a covered outdoor patio with a gas fireplace, and an outdoor shower. Back inside, two additional guest bedrooms share a full bath on the second floor, while downstairs, two large recreation rooms offer further customization and flexibility. The location is just as compelling as the house itself, minutes from Goose Creek Beach, Cedar Beach, Croteaux Vineyards, and the many shops and restaurants of Southold Hamlet. This is a special property with a real point of view that you'll look forward to walking into each time you return home.

605 Cedar Drive, Southold

$2,650,000

This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

4 Beds ⋅ 4 Baths ⋅ 1023134 MLS

This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

195 Williamsburg Drive, Southold

$2,595,000

Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers sweeping water views, sensational sunsets, and effortless coastal living. Renovated in 2016 and completely move-in ready, the home blends sophisticated style with relaxed comfort, creating the perfect setting for both entertaining and quiet moments by the sea. Thoughtful upgrades include radiant floor heating, ducted heating and cooling with remote access, marble countertops, updated mirrors and light fixtures, keyless entry, Sonos speakers, and a beautifully appointed chef's kitchen. The primary suite includes a gorgeous bathroom, featuring a sculptural egg-shaped soaking tub perfectly positioned to capture the sunset views, separate shower and double sinks. The primary also has an office nook, and custom walk-in closet. Outdoor living is at the heart of the property. An expansive sun deck provides ample space for dining, lounging, entertaining, or morning yoga, while private stairs lead directly to the sea. A rare grandfathered lower waterfront platform creates an extraordinary setting at the water's edge for cocktails, Pilates, or simply taking in the sights and sounds of the Sound. The outdoor audio system extends the experience all the way to the property's iconic Whale Rock. Additional highlights include a detached garage offering potential for conversion into additional living space with proper permits. With dramatic water views, unforgettable sunsets, and a lifestyle centered around the Sound, this is North Fork waterfront living at its finest.

3 Beds ⋅ 2 Baths ⋅ 1033102 MLS

Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers sweeping water views, sensational sunsets, and effortless coastal living. Renovated in 2016 and completely move-in ready, the home blends sophisticated style with relaxed comfort, creating the perfect setting for both entertaining and quiet moments by the sea. Thoughtful upgrades include radiant floor heating, ducted heating and cooling with remote access, marble countertops, updated mirrors and light fixtures, keyless entry, Sonos speakers, and a beautifully appointed chef's kitchen. The primary suite includes a gorgeous bathroom, featuring a sculptural egg-shaped soaking tub perfectly positioned to capture the sunset views, separate shower and double sinks. The primary also has an office nook, and custom walk-in closet. Outdoor living is at the heart of the property. An expansive sun deck provides ample space for dining, lounging, entertaining, or morning yoga, while private stairs lead directly to the sea. A rare grandfathered lower waterfront platform creates an extraordinary setting at the water's edge for cocktails, Pilates, or simply taking in the sights and sounds of the Sound. The outdoor audio system extends the experience all the way to the property's iconic Whale Rock. Additional highlights include a detached garage offering potential for conversion into additional living space with proper permits. With dramatic water views, unforgettable sunsets, and a lifestyle centered around the Sound, this is North Fork waterfront living at its finest.

21515 Soundview Avenue, Southold

$2,399,000

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!!!

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

$2,200,000

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

3 Beds ⋅ 3 Baths ⋅ 1038709 MLS

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

225 Lakeside Drive S, Southold

$2,150,000

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

3 Beds ⋅ 2 Baths ⋅ 1058940 MLS

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

1455 Cedar Point Drive E, Southold

$1,999,999

Rarely does a Southold waterfront property offer such a compelling combination of privacy, direct bay access, and expansive water views. Set on a protected inlet with a permitted dock and kayak launch, this three-bedroom, three-bath home is designed around its extraordinary setting. Sun-filled rooms open to a supersized waterfront deck, with a chef's kitchen with soapstone counters, a welcoming living room with fireplace, and water views throughout. The first-floor primary suite is a quiet retreat, and a rooftop observation deck captures sweeping vistas across Little Peconic Bay. The permitted lower level adds two bedrooms, a bath, a den, a second fireplace, and a wine cellar, with sliding doors opening to the water. The next owner also inherits a head start. The sellers have applied for a pool permit, so approvals are already in motion, and they have applied for a Grant toward a new IA septic system that transfers with the property. Approximately 3,900 square feet of finished living space on a half-acre, plus a one-car garage and shed, in a truly special Southold waterfront setting.

3 Beds ⋅ 3 Baths ⋅ 1022803 MLS

Rarely does a Southold waterfront property offer such a compelling combination of privacy, direct bay access, and expansive water views. Set on a protected inlet with a permitted dock and kayak launch, this three-bedroom, three-bath home is designed around its extraordinary setting. Sun-filled rooms open to a supersized waterfront deck, with a chef's kitchen with soapstone counters, a welcoming living room with fireplace, and water views throughout. The first-floor primary suite is a quiet retreat, and a rooftop observation deck captures sweeping vistas across Little Peconic Bay. The permitted lower level adds two bedrooms, a bath, a den, a second fireplace, and a wine cellar, with sliding doors opening to the water. The next owner also inherits a head start. The sellers have applied for a pool permit, so approvals are already in motion, and they have applied for a Grant toward a new IA septic system that transfers with the property. Approximately 3,900 square feet of finished living space on a half-acre, plus a one-car garage and shed, in a truly special Southold waterfront setting.

2245 Little Peconic Bay Lane, Southold

$1,750,000

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.**

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

$1,695,000

For Sale - Zoned Hamlet Business Turnkey Commercial Property with Apartment - Prime Beach Route Location! Incredible opportunity to own a fully equipped commercial property with a 2-bedroom, 1-bath apartment above - perfect for owner-operators or investors! Located on a high-traffic road leading directly to the beach, this versatile space is ideal for a cafe, deli, bakery, specialty food business, or retail shop. The building features a fully operational commercial kitchen, walk-in freezer, and walk-in refrigerator in the basement - ready for immediate use. Upstairs, enjoy a spacious 2-bedroom apartment with full kitchen and bath, ideal for live/work convenience or additional rental income.

909437 MLS

For Sale - Zoned Hamlet Business Turnkey Commercial Property with Apartment - Prime Beach Route Location! Incredible opportunity to own a fully equipped commercial property with a 2-bedroom, 1-bath apartment above - perfect for owner-operators or investors! Located on a high-traffic road leading directly to the beach, this versatile space is ideal for a cafe, deli, bakery, specialty food business, or retail shop. The building features a fully operational commercial kitchen, walk-in freezer, and walk-in refrigerator in the basement - ready for immediate use. Upstairs, enjoy a spacious 2-bedroom apartment with full kitchen and bath, ideal for live/work convenience or additional rental income.

55700 Route 25, Southold

$1,600,000

2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. Four Buildings Possible As Of Right. Excellent Route 25 Exposure & Great Location In Center Of The Hamlet! Commercial Listing MLS# 3530579

L3530714 MLS

2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. Four Buildings Possible As Of Right. Excellent Route 25 Exposure & Great Location In Center Of The Hamlet! Commercial Listing MLS# 3530579

55975 Route 25, Southold

$1,600,000

2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center of Hamlet! Land Listing MLS# 3530714

L3530579 MLS

2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center of Hamlet! Land Listing MLS# 3530714

55975 Route 25, Southold

$1,599,000

Experience the best of North Fork living in this stunning new construction home offering beautiful water views and deeded beach access. Thoughtfully designed with modern coastal elegance, this residence blends quality craftsmanship, open-concept living, and effortless indoor-outdoor flow. The main living area is filled with natural light and showcases spacious interiors, elevated finishes, and a seamless connection to the surrounding landscape. A beautifully appointed kitchen, generous entertaining spaces, and well-designed bedroom suites create the perfect balance of comfort and sophistication. The home also includes a full basement with egress, offering excellent potential to be finished to suit your needs such as additional living space, recreation, fitness, media, or storage. The property includes full landscaping and offers room for a pool, creating the opportunity to design your ideal outdoor retreat. Enjoy peaceful water views, coastal breezes, and direct access to a private deeded beach which is ideal for kayaking, paddleboarding, swimming, or simply relaxing by the shore. Perfectly situated near North Fork vineyards, farm stands, restaurants, marinas, and village amenities, this home offers a rare opportunity to enjoy new construction with true coastal lifestyle appeal. A refined North Fork retreat designed for year-round living, weekend escapes, and effortless entertainment.

4 Beds ⋅ 4 Baths ⋅ 1011372 MLS

Experience the best of North Fork living in this stunning new construction home offering beautiful water views and deeded beach access. Thoughtfully designed with modern coastal elegance, this residence blends quality craftsmanship, open-concept living, and effortless indoor-outdoor flow. The main living area is filled with natural light and showcases spacious interiors, elevated finishes, and a seamless connection to the surrounding landscape. A beautifully appointed kitchen, generous entertaining spaces, and well-designed bedroom suites create the perfect balance of comfort and sophistication. The home also includes a full basement with egress, offering excellent potential to be finished to suit your needs such as additional living space, recreation, fitness, media, or storage. The property includes full landscaping and offers room for a pool, creating the opportunity to design your ideal outdoor retreat. Enjoy peaceful water views, coastal breezes, and direct access to a private deeded beach which is ideal for kayaking, paddleboarding, swimming, or simply relaxing by the shore. Perfectly situated near North Fork vineyards, farm stands, restaurants, marinas, and village amenities, this home offers a rare opportunity to enjoy new construction with true coastal lifestyle appeal. A refined North Fork retreat designed for year-round living, weekend escapes, and effortless entertainment.

1700 Smith Drive S, Southold

$1,550,000

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!

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

$1,499,000

Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards, marinas, golfing, boutique shopping, galleries, and more. A once in a lifetime opportunity to build your dream estate - perfect for an all inclusive equestrian facility. All with the utmost privacy in this amazing piece of paradise. Potential for 2 acre subdivision.

827387 MLS

Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards, marinas, golfing, boutique shopping, galleries, and more. A once in a lifetime opportunity to build your dream estate - perfect for an all inclusive equestrian facility. All with the utmost privacy in this amazing piece of paradise. Potential for 2 acre subdivision.

11200 N Bayview Road, Southold

$1,495,000

Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes from Southold Village, beaches, vineyards and celebrated local restaurants. Property is being sold as-is.

4 Beds ⋅ 4 Baths ⋅ 1051232 MLS

Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes from Southold Village, beaches, vineyards and celebrated local restaurants. Property is being sold as-is.

3995 Wells Avenue, Southold