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ROMANTIC WATERFRONT LIVING There are a finite number of properties that exist beyond the everyday. Specifically, one where 604 feet of private beach meets the endless horizon of the Long Island Sound, and a cottage sits quietly amongst the landscape as though it's always belonged there. This is the one. The setting speaks louder than any renovation could. Morning light spills across the water. Evening brings that stillness that only waterfront sanctuaries know. The beach stretches long and uninterrupted, a rare luxury on the North Fork where sound frontage of this magnitude simply doesn't come available. The cottage itself? Charmingly unassuming. It understands its role here-to frame the views, shelter you from the wind, and otherwise stay out of nature's way. There's an honesty to its rustic character that feels increasingly rare. What you're really acquiring is 604 feet of your own coastline in one of the most coveted corridors of the North Fork. This is the setting that stops conversation mid-sentence. The kind of place that makes you forget what day it is. Raw, romantic, and utterly uncommon - a Soundfront opportunity that simply doesn't surface often on the North Fork!

2 Beds ⋅ 3 Baths ⋅ 929544 MLS

ROMANTIC WATERFRONT LIVING There are a finite number of properties that exist beyond the everyday. Specifically, one where 604 feet of private beach meets the endless horizon of the Long Island Sound, and a cottage sits quietly amongst the landscape as though it's always belonged there. This is the one. The setting speaks louder than any renovation could. Morning light spills across the water. Evening brings that stillness that only waterfront sanctuaries know. The beach stretches long and uninterrupted, a rare luxury on the North Fork where sound frontage of this magnitude simply doesn't come available. The cottage itself? Charmingly unassuming. It understands its role here-to frame the views, shelter you from the wind, and otherwise stay out of nature's way. There's an honesty to its rustic character that feels increasingly rare. What you're really acquiring is 604 feet of your own coastline in one of the most coveted corridors of the North Fork. This is the setting that stops conversation mid-sentence. The kind of place that makes you forget what day it is. Raw, romantic, and utterly uncommon - a Soundfront opportunity that simply doesn't surface often on the North Fork!

East Marion

$4,000,000

This Sound Front home at the edge of a quiet Orient cul-de-sac is more than a haven-it's a destination for those who appreciate the rare union of luxury, privacy, and personality. Here, drama is found in the sweep of panoramic water views and the hush of mornings on a private deck, just upstairs from your own sandy shoreline. Step into soaring, sunlit spaces designed for living boldly: a cathedral-ceilinged great room crowned by a Niamh Barry light sculpture, six uniquely serene bedrooms, and a media lounge fit for both celebration and retreat. Two grand spiral staircases anchor the heart of the home, while an elevator ensures every level is effortless. This is a house that thinks ahead-10-foot ceilings, custom red oak flooring, radiant heat where you want it, a climate-controlled wine room, a butler's pantry for flawless entertaining, and double laundry rooms for seamless living. Outside, a 34'x13' Gunite heated infinity pool and 8'x8' spa blend into Sound views, with private stairs leading to the beach for spontaneous escapes. Security, comfort, and modern ease are ever-present with remote cameras, central vacuum, a triple-car garage, a full-house generator, and avant-garde HVAC and audio systems-leaving you free to focus on what really matters: sunrises, open water, and time well spent. For those who believe a home should never feel ordinary-this Orient retreat awaits.

6 Beds ⋅ 7 Baths ⋅ 918863 MLS

This Sound Front home at the edge of a quiet Orient cul-de-sac is more than a haven-it's a destination for those who appreciate the rare union of luxury, privacy, and personality. Here, drama is found in the sweep of panoramic water views and the hush of mornings on a private deck, just upstairs from your own sandy shoreline. Step into soaring, sunlit spaces designed for living boldly: a cathedral-ceilinged great room crowned by a Niamh Barry light sculpture, six uniquely serene bedrooms, and a media lounge fit for both celebration and retreat. Two grand spiral staircases anchor the heart of the home, while an elevator ensures every level is effortless. This is a house that thinks ahead-10-foot ceilings, custom red oak flooring, radiant heat where you want it, a climate-controlled wine room, a butler's pantry for flawless entertaining, and double laundry rooms for seamless living. Outside, a 34'x13' Gunite heated infinity pool and 8'x8' spa blend into Sound views, with private stairs leading to the beach for spontaneous escapes. Security, comfort, and modern ease are ever-present with remote cameras, central vacuum, a triple-car garage, a full-house generator, and avant-garde HVAC and audio systems-leaving you free to focus on what really matters: sunrises, open water, and time well spent. For those who believe a home should never feel ordinary-this Orient retreat awaits.

2670 Grandview Drive, Orient

$3,150,000

Designed by celebrated architect Richard Gluckman, this contemporary waterfront residence sits along one of Orient’s most coveted stretches of coastline in the enclave of Browns Hills. Perfectly positioned for privacy on a generous 1.25-acre lot, the land’s natural elevation affords sweeping Long Island Sound views from nearly every room. A great room with soaring ceilings and a wood-burning fireplace anchors the main level, flowing seamlessly into the kitchen and adjacent dining area—ideal for entertaining. The eastern wing features an en-suite bedroom, well-positioned as a quiet respite for guests. Upstairs, the primary suite includes an en-suite bath and a separate office providing additional flexible space. The expansive grounds offer ample room for a pool or future expansion and are home to a diverse array of birdlife and native plantings, enhancing the tranquility of this coastal retreat. Across the rolling lawn is access to a private beach for sunsets, swims, and picnic dinners. Ideally located minutes from Orient and Greenport Villages and the Cross Sound Ferry to New England, this is a rare opportunity to own a thoughtfully designed modern home in one of the North Fork’s most desirable settings.

3 Beds ⋅ 3 Baths ⋅ 924682 MLS

Designed by celebrated architect Richard Gluckman, this contemporary waterfront residence sits along one of Orient’s most coveted stretches of coastline in the enclave of Browns Hills. Perfectly positioned for privacy on a generous 1.25-acre lot, the land’s natural elevation affords sweeping Long Island Sound views from nearly every room. A great room with soaring ceilings and a wood-burning fireplace anchors the main level, flowing seamlessly into the kitchen and adjacent dining area—ideal for entertaining. The eastern wing features an en-suite bedroom, well-positioned as a quiet respite for guests. Upstairs, the primary suite includes an en-suite bath and a separate office providing additional flexible space. The expansive grounds offer ample room for a pool or future expansion and are home to a diverse array of birdlife and native plantings, enhancing the tranquility of this coastal retreat. Across the rolling lawn is access to a private beach for sunsets, swims, and picnic dinners. Ideally located minutes from Orient and Greenport Villages and the Cross Sound Ferry to New England, this is a rare opportunity to own a thoughtfully designed modern home in one of the North Fork’s most desirable settings.

900 N View Drive, Orient

$2,900,000

"Precision In Every Detail. Elevated Living Throughout" - Set within a private enclave moments from the Peconic Bay, this newly constructed home delivers a refined living experience defined by custom craftsmanship, scale, and seamless indoor-outdoor flow. Every element has been thoughtfully curated, blending clean architectural lines with bespoke materials and elevated finishes throughout. At the heart of the home, a striking chef’s kitchen anchors the main living space—appointed with quartz countertops, custom white oak cabinetry with lighting, Kohler workstation sink and a full suite of Miele appliances. Designed for both everyday living and elevated entertaining, the open-concept layout transitions effortlessly into expansive living and dining areas, where soaring ceilings, abundant natural light, solid white oak wood 6" plank floors and a custom stone fireplace anchored by bookcases create a warm yet sophisticated atmosphere. Bedrooms and bathrooms are designed as private retreats, featuring refined finishes, generous proportions, and a calm, modern aesthetic. A first floor primary ensuite offers the ultimate in convenience and privacy, creating a true main level retreat with exceptional finishes, flawless primary bathroom, expansive custom finished walk in closet and all with a well proportioned layout. The outdoor setting is equally compelling, offering a resort-inspired setting complete with a heated saltwater pool with custom waterfall, expansive bluestone slate patio, and built-in fireplace—ideal for hosting or unwinding in total privacy. The offering is further elevated by private association beach access to the Peconic Bay, perfectly suited for effortless trips by golf cart, which is included, creating a seamless connection between home and shoreline. Every detail, from the curated landscaping to the integrated lighting, enhances both ambiance and usability from day to evening. The home is equipped with a fully integrated custom home automation system, delivering intuitive control over lighting, climate, sound, and security. A generator hook up will ensure uninterrupted comfort, while thoughtful additions such as a golf cart—perfect for easy access to nearby waterfront and community amenities—further elevate the lifestyle offering. Each space reflects the same level of detail and intention found throughout the home. An unmatched opportunity to own a turnkey, showstopping residence where design, technology, and lifestyle converge—crafted for those who value both precision and presence. This listing may include images that have been digitally altered or virtually staged.

4 Beds ⋅ 7 Baths ⋅ 968387 MLS

"Precision In Every Detail. Elevated Living Throughout" - Set within a private enclave moments from the Peconic Bay, this newly constructed home delivers a refined living experience defined by custom craftsmanship, scale, and seamless indoor-outdoor flow. Every element has been thoughtfully curated, blending clean architectural lines with bespoke materials and elevated finishes throughout. At the heart of the home, a striking chef’s kitchen anchors the main living space—appointed with quartz countertops, custom white oak cabinetry with lighting, Kohler workstation sink and a full suite of Miele appliances. Designed for both everyday living and elevated entertaining, the open-concept layout transitions effortlessly into expansive living and dining areas, where soaring ceilings, abundant natural light, solid white oak wood 6" plank floors and a custom stone fireplace anchored by bookcases create a warm yet sophisticated atmosphere. Bedrooms and bathrooms are designed as private retreats, featuring refined finishes, generous proportions, and a calm, modern aesthetic. A first floor primary ensuite offers the ultimate in convenience and privacy, creating a true main level retreat with exceptional finishes, flawless primary bathroom, expansive custom finished walk in closet and all with a well proportioned layout. The outdoor setting is equally compelling, offering a resort-inspired setting complete with a heated saltwater pool with custom waterfall, expansive bluestone slate patio, and built-in fireplace—ideal for hosting or unwinding in total privacy. The offering is further elevated by private association beach access to the Peconic Bay, perfectly suited for effortless trips by golf cart, which is included, creating a seamless connection between home and shoreline. Every detail, from the curated landscaping to the integrated lighting, enhances both ambiance and usability from day to evening. The home is equipped with a fully integrated custom home automation system, delivering intuitive control over lighting, climate, sound, and security. A generator hook up will ensure uninterrupted comfort, while thoughtful additions such as a golf cart—perfect for easy access to nearby waterfront and community amenities—further elevate the lifestyle offering. Each space reflects the same level of detail and intention found throughout the home. An unmatched opportunity to own a turnkey, showstopping residence where design, technology, and lifestyle converge—crafted for those who value both precision and presence. This listing may include images that have been digitally altered or virtually staged.

250 Osprey Nest Road, Greenport

$2,500,000

Presenting a rare waterfront property in Greenport, for the serious boater. This remarkable home features over 150 feet of waterfront on protected Stirling Harbor, offering the deep water dock space you've been waiting for. The luxury floating dock can easily accommodate oversized vessels, making it ideal for large yachts. Less than 3 years old, it has both 85 feet and 30 feet deep-water sides and is fully serviced with 200 amps of power and internet. Plenty of space for multiple boats, kayaks and friends to pull up waterside. Stirling Harbor offers big-boat access with an 8 foot maintained channel and calm water protection. Also perfect for quick runs to Gardiners Bay and Shelter Island. This very spacious 4-bedroom, 3-full bath home is in excellent condition and boasts wood floors throughout, an open floor plan, fireplace and central air conditioning. At the heart of the home is a sleek chef's kitchen with stainless steel appliances, kitchen island and a separate sunken dining room with direct water views. Step into the modern living room with fireplace, offering seamless indoor outdoor living with a large waterfront deck perfect for al fresco dining. First floor also boasts 3 large guest bedrooms with closets, 2 spa bathrooms, a laundry room and an oversized garage. The spacious second floor primary suite includes a living area, ensuite bathroom, walk-in closet and private walk-out balcony, perfect for enjoying the serene harbor views. Master suite could also double as a separate guest quarters, offering plenty of space for a large family. Beyond the unparalleled boating amenities, the property offers a prime Greenport location. You can easily bike to sandy beaches, award-winning vineyards or take a leisurely stroll into the charming Greenport Village full of restaurants, galleries, movie theater, fitness studios, fine shopping and ferry to Shelter Island and Hamptons. Greenport offers an easy commute (99 miles) to NYC via LIRR train or Hampton Jitney bus. Room for a future in-ground pool. This property offers a unique opportunity for those seeking a luxurious waterfront lifestyle with direct access to superb boating. Schedule a private viewing before this rare opportunity has left the dock!

4 Beds ⋅ 3 Baths ⋅ 935398 MLS

Presenting a rare waterfront property in Greenport, for the serious boater. This remarkable home features over 150 feet of waterfront on protected Stirling Harbor, offering the deep water dock space you've been waiting for. The luxury floating dock can easily accommodate oversized vessels, making it ideal for large yachts. Less than 3 years old, it has both 85 feet and 30 feet deep-water sides and is fully serviced with 200 amps of power and internet. Plenty of space for multiple boats, kayaks and friends to pull up waterside. Stirling Harbor offers big-boat access with an 8 foot maintained channel and calm water protection. Also perfect for quick runs to Gardiners Bay and Shelter Island. This very spacious 4-bedroom, 3-full bath home is in excellent condition and boasts wood floors throughout, an open floor plan, fireplace and central air conditioning. At the heart of the home is a sleek chef's kitchen with stainless steel appliances, kitchen island and a separate sunken dining room with direct water views. Step into the modern living room with fireplace, offering seamless indoor outdoor living with a large waterfront deck perfect for al fresco dining. First floor also boasts 3 large guest bedrooms with closets, 2 spa bathrooms, a laundry room and an oversized garage. The spacious second floor primary suite includes a living area, ensuite bathroom, walk-in closet and private walk-out balcony, perfect for enjoying the serene harbor views. Master suite could also double as a separate guest quarters, offering plenty of space for a large family. Beyond the unparalleled boating amenities, the property offers a prime Greenport location. You can easily bike to sandy beaches, award-winning vineyards or take a leisurely stroll into the charming Greenport Village full of restaurants, galleries, movie theater, fitness studios, fine shopping and ferry to Shelter Island and Hamptons. Greenport offers an easy commute (99 miles) to NYC via LIRR train or Hampton Jitney bus. Room for a future in-ground pool. This property offers a unique opportunity for those seeking a luxurious waterfront lifestyle with direct access to superb boating. Schedule a private viewing before this rare opportunity has left the dock!

340 Robinson Road, Greenport

$2,225,000

BONUS: Upon request builder will include a custom built 12x12 pool shed with the same materials and style identical to the house. Entire house completed and beautifully landscaped!!! With incredible water views and access to a picturesque private beach, 285 Blue Marlin exemplifies luxury coastal living at its finest. Constructed by the North Fork’s most revered builders, no expense has been spared and the utmost attention to detail is evident with attributes such as designer fixtures, outfitted closets, Emtek hardware, Maibec treated cedar siding and a balcony off of two bedrooms - perfect for enjoying those glistening water views. A seamlessly connected open-concept first floor, 9' ceilings, an eat-in chef's kitchen with Thermadore appliances, marble counter tops and 4 ensuite bedrooms are to name but just a few of the well thought out features which make this home the ideal entertainer's delight. Whether you are enjoying your morning coffee on the welcoming covered front porch, sipping wine by the pool or cozying up in the family room with the gas fireplace during those brisk fall and winter months, this home is sure to satisfy the most discerning buyer. A mudroom, laundry room and powder room are also cleverly situated, tucked behind the custom kitchen. A shy half-acre corner property with saltwater pool, paved patio, outdoor shower and an attached two-car garage complete this special home. Come and make it yours! Please see the virtual tour link.

4 Beds ⋅ 5 Baths ⋅ 862752 MLS

BONUS: Upon request builder will include a custom built 12x12 pool shed with the same materials and style identical to the house. Entire house completed and beautifully landscaped!!! With incredible water views and access to a picturesque private beach, 285 Blue Marlin exemplifies luxury coastal living at its finest. Constructed by the North Fork’s most revered builders, no expense has been spared and the utmost attention to detail is evident with attributes such as designer fixtures, outfitted closets, Emtek hardware, Maibec treated cedar siding and a balcony off of two bedrooms - perfect for enjoying those glistening water views. A seamlessly connected open-concept first floor, 9' ceilings, an eat-in chef's kitchen with Thermadore appliances, marble counter tops and 4 ensuite bedrooms are to name but just a few of the well thought out features which make this home the ideal entertainer's delight. Whether you are enjoying your morning coffee on the welcoming covered front porch, sipping wine by the pool or cozying up in the family room with the gas fireplace during those brisk fall and winter months, this home is sure to satisfy the most discerning buyer. A mudroom, laundry room and powder room are also cleverly situated, tucked behind the custom kitchen. A shy half-acre corner property with saltwater pool, paved patio, outdoor shower and an attached two-car garage complete this special home. Come and make it yours! Please see the virtual tour link.

285 Blue Marlin Drive, Southold

$2,150,000

Perched atop the bluffs of the Long Island Sound, this carefully designed showstopper is located within the desirable Eastern Stirling Shores community, offering private beach access just a short walk away. The rear yard provides a true resort-style setting, where you can bask in full sun poolside beside the natural gas–heated, in-ground saltwater pool with electric cover, all while enjoying exceptional privacy created by mature privet hedges surrounding the property. Inside, the home features beautiful white oak floors throughout and a stunning chef’s kitchen anchored by a dramatic waterfall stone island. The main level offers one of two primary en-suite bedrooms complete with dual walk-in closets, along with a full-size laundry room with sink, pantry, half bath, and multiple living spaces centered around a gas fireplace. The second floor features a second primary en-suite bedroom with a spacious walk-in closet, private bathroom, and a balcony capturing water views of the Long Island Sound. This level also includes an additional stacked laundry area and three more en-suite bedrooms, each with its own private bathroom and balcony access. Completing the home is a large attached two-car garage that flows seamlessly into the main living area, as well as a third garage located beneath the main level. A spacious walk-out basement with high ceilings offers the opportunity to easily finish over 1,000 additional square feet of living space. Offering an exceptional blend of location, amenities, and turnkey condition, this impressive home delivers the very best of North Fork coastal living.

5 Beds ⋅ 6 Baths ⋅ 975661 MLS

Perched atop the bluffs of the Long Island Sound, this carefully designed showstopper is located within the desirable Eastern Stirling Shores community, offering private beach access just a short walk away. The rear yard provides a true resort-style setting, where you can bask in full sun poolside beside the natural gas–heated, in-ground saltwater pool with electric cover, all while enjoying exceptional privacy created by mature privet hedges surrounding the property. Inside, the home features beautiful white oak floors throughout and a stunning chef’s kitchen anchored by a dramatic waterfall stone island. The main level offers one of two primary en-suite bedrooms complete with dual walk-in closets, along with a full-size laundry room with sink, pantry, half bath, and multiple living spaces centered around a gas fireplace. The second floor features a second primary en-suite bedroom with a spacious walk-in closet, private bathroom, and a balcony capturing water views of the Long Island Sound. This level also includes an additional stacked laundry area and three more en-suite bedrooms, each with its own private bathroom and balcony access. Completing the home is a large attached two-car garage that flows seamlessly into the main living area, as well as a third garage located beneath the main level. A spacious walk-out basement with high ceilings offers the opportunity to easily finish over 1,000 additional square feet of living space. Offering an exceptional blend of location, amenities, and turnkey condition, this impressive home delivers the very best of North Fork coastal living.

2375 Sound Drive, Greenport

$2,142,500

Set directly on the Long Island Sound, this waterfront home offers a rare opportunity to create something truly special in an exceptional location. Enjoy spectacular sunsets and water views from this gracious residence featuring 4 bedrooms and 3 full baths, including a primary suite on the first floor. The open floor plan is anchored by a spacious great room with a wood-burning fireplace, ideal for relaxed coastal living and entertaining. A full basement with high ceilings provides excellent potential for additional finished living space. Additional highlights include a generator, roof replaced in 2015, and deeded beach rights with beach access just a stone’s throw away. With vision and updates, this sound-front property can be transformed into an extraordinary waterfront retreat.

4 Beds ⋅ 3 Baths ⋅ 951049 MLS

Set directly on the Long Island Sound, this waterfront home offers a rare opportunity to create something truly special in an exceptional location. Enjoy spectacular sunsets and water views from this gracious residence featuring 4 bedrooms and 3 full baths, including a primary suite on the first floor. The open floor plan is anchored by a spacious great room with a wood-burning fireplace, ideal for relaxed coastal living and entertaining. A full basement with high ceilings provides excellent potential for additional finished living space. Additional highlights include a generator, roof replaced in 2015, and deeded beach rights with beach access just a stone’s throw away. With vision and updates, this sound-front property can be transformed into an extraordinary waterfront retreat.

3200 Sound Drive, Greenport

$2,140,000

The crown jewel of Orient Village, the Shaw House/ Revolutionary Cottage was built in 1730 and features 3 bedrooms, 2.5 baths, and an updated eat-in kitchen. Original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. Two large decks span the back of the house overlooking Orient Harbor & Yacht Club. Located in the heart of Orient Village walking/biking to all village amenities. 48 hr notice for showings.

3 Beds ⋅ 3 Baths ⋅ 982490 MLS

The crown jewel of Orient Village, the Shaw House/ Revolutionary Cottage was built in 1730 and features 3 bedrooms, 2.5 baths, and an updated eat-in kitchen. Original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. Two large decks span the back of the house overlooking Orient Harbor & Yacht Club. Located in the heart of Orient Village walking/biking to all village amenities. 48 hr notice for showings.

1970 Village Lane, Orient

$2,100,000

Set in the heart of Orient’s bucolic Browns Hills, this light-filled contemporary residence offers an exceptional blend of privacy, design, and landscape. Expansive views stretch across open pastoral fields to the bay beyond, creating a setting that feels both peaceful and uniquely North Fork. Spanning three levels, the home features a highly functional floor plan with three bedrooms and three baths, thoughtfully arranged to provide flexibility and comfortable separation of space. Large windows and multiple exposures fill the interior with natural light while framing the surrounding scenery throughout the day. Outside, beautifully developed landscaping surrounds a heated saltwater gunite pool, expansive decking, and outdoor shower, creating an ideal environment for entertaining or quiet summer living. Association access to your Sound Beach completes the offering, adding easy waterfront enjoyment to this serene Orient retreat.

3 Beds ⋅ 3 Baths ⋅ 997654 MLS

Set in the heart of Orient’s bucolic Browns Hills, this light-filled contemporary residence offers an exceptional blend of privacy, design, and landscape. Expansive views stretch across open pastoral fields to the bay beyond, creating a setting that feels both peaceful and uniquely North Fork. Spanning three levels, the home features a highly functional floor plan with three bedrooms and three baths, thoughtfully arranged to provide flexibility and comfortable separation of space. Large windows and multiple exposures fill the interior with natural light while framing the surrounding scenery throughout the day. Outside, beautifully developed landscaping surrounds a heated saltwater gunite pool, expansive decking, and outdoor shower, creating an ideal environment for entertaining or quiet summer living. Association access to your Sound Beach completes the offering, adding easy waterfront enjoyment to this serene Orient retreat.

255 S View Drive, Orient

$2,046,000

Welcome to your bayside escape. A stunning bayfront retreat offering direct access to the beach and breathtaking panoramic views from the primary suite, living room, and sunroom. Designed for seamless indoor-outdoor living, this home is perfectly situated in one of East Marion's most sought-after beach communities. Inside, a warm and inviting interior creates an atmosphere of comfort and relaxation. The primary suite serves as a private sanctuary, complete with a balcony that captures spectacular sunrise and sunset vistas over the bay-an ideal spot for morning coffee or evening unwinding. A spacious semi-attached garage provides plenty of room for beach gear and water toys. Whether you're looking for a tranquil weekend escape or a year-round coastal haven, this bayfront treasure effortlessly combines laid-back luxury with an unparalleled location.

4 Beds ⋅ 3 Baths ⋅ 918826 MLS

Welcome to your bayside escape. A stunning bayfront retreat offering direct access to the beach and breathtaking panoramic views from the primary suite, living room, and sunroom. Designed for seamless indoor-outdoor living, this home is perfectly situated in one of East Marion's most sought-after beach communities. Inside, a warm and inviting interior creates an atmosphere of comfort and relaxation. The primary suite serves as a private sanctuary, complete with a balcony that captures spectacular sunrise and sunset vistas over the bay-an ideal spot for morning coffee or evening unwinding. A spacious semi-attached garage provides plenty of room for beach gear and water toys. Whether you're looking for a tranquil weekend escape or a year-round coastal haven, this bayfront treasure effortlessly combines laid-back luxury with an unparalleled location.

500 South Lane, East Marion

$2,025,000

Ideally located just minutes from the heart of historic Greenport, this beautifully crafted home offers the perfect blend of coastal elegance and modern comfort. Enjoy access to the serene shores of Peconic Bay where tranquil waters and scenic views invite daily relaxation. Entertain and impress your guests from the bricked patio, and heated saltwater pool. Professional, lush landscaped grounds and local produce from the farm around the road completes the Farm to Table setting! Experience the perfect blend of comfort and classic charm in this stunning 2-year-old farmhouse with expansive water views from multiple rooms. This beauty is located in the coveted Peconic Bay Estates. Meticulously designed and ready for immediate enjoyment, custom details, 4-bedroom, 3.5-bathroom home offers spacious, light-filled living crafted for both relaxation and sophistication. A bright and airy home office offers sweeping views of Greenport’s waterways truly an inspiring place to work or create. Whether you’re strolling the quaint streets of Greenport or enjoying the natural beauty right outside your door, this property offers a lifestyle rich in charm and convenience.

4 Beds ⋅ 4 Baths ⋅ 853979 MLS

Ideally located just minutes from the heart of historic Greenport, this beautifully crafted home offers the perfect blend of coastal elegance and modern comfort. Enjoy access to the serene shores of Peconic Bay where tranquil waters and scenic views invite daily relaxation. Entertain and impress your guests from the bricked patio, and heated saltwater pool. Professional, lush landscaped grounds and local produce from the farm around the road completes the Farm to Table setting! Experience the perfect blend of comfort and classic charm in this stunning 2-year-old farmhouse with expansive water views from multiple rooms. This beauty is located in the coveted Peconic Bay Estates. Meticulously designed and ready for immediate enjoyment, custom details, 4-bedroom, 3.5-bathroom home offers spacious, light-filled living crafted for both relaxation and sophistication. A bright and airy home office offers sweeping views of Greenport’s waterways truly an inspiring place to work or create. Whether you’re strolling the quaint streets of Greenport or enjoying the natural beauty right outside your door, this property offers a lifestyle rich in charm and convenience.

3200 Bay Shore Road, Greenport

$1,943,000

Waterfront dream! This 3-bed, 2.5-bath home boasts safe deep-water docking on 50' wide canal. Open floor plan on both levels features two stone fireplaces, primary en-suite, ample storage, and a large open kitchen with breakfast and dining areas. Enjoy large sliders accessing two decks overlooking the waterfront, plus a spacious waterside boat house Benefit from a brand new bulkhead ramp, floater & decking completed in 2025, Deeded Beach Rights around the corner. new Central Air Compressor 2025. Built by Deck Homes for guaranteed quality!

3 Beds ⋅ 3 Baths ⋅ 939699 MLS

Waterfront dream! This 3-bed, 2.5-bath home boasts safe deep-water docking on 50' wide canal. Open floor plan on both levels features two stone fireplaces, primary en-suite, ample storage, and a large open kitchen with breakfast and dining areas. Enjoy large sliders accessing two decks overlooking the waterfront, plus a spacious waterside boat house Benefit from a brand new bulkhead ramp, floater & decking completed in 2025, Deeded Beach Rights around the corner. new Central Air Compressor 2025. Built by Deck Homes for guaranteed quality!

630 Tarpon Drive, Southold

$1,900,000

Treat yourself to the astounding panoramic waterviews afforded by this feature-rich luxury home set in the most-easterly enclave on Long Island’s beautiful North Fork. From the full-length living-level deck, Long Island Sound and the Connecticut shoreline beckon to the north; east and south are striking views of Plum Island and Gardiners Bay. Passing through stone pillars and an arched privacy gate, you will first behold this handsome spectacularly built home over the length of the vast brick driveway. Designed and crafted without regard to expense, the home’s deft use of space and robust construction maximize the remarkable water views, provide gracious living spaces, and yield exceptional pride of ownership. Lavish with amenities, including three fireplaces, Viking chef’s kitchen, and a cherry-panelled elevator, it is set on tastefully landscaped grounds of nearly an acre, with ample room for a large pool and tennis. Come home soon!

4 Beds ⋅ 4 Baths ⋅ 956958 MLS

Treat yourself to the astounding panoramic waterviews afforded by this feature-rich luxury home set in the most-easterly enclave on Long Island’s beautiful North Fork. From the full-length living-level deck, Long Island Sound and the Connecticut shoreline beckon to the north; east and south are striking views of Plum Island and Gardiners Bay. Passing through stone pillars and an arched privacy gate, you will first behold this handsome spectacularly built home over the length of the vast brick driveway. Designed and crafted without regard to expense, the home’s deft use of space and robust construction maximize the remarkable water views, provide gracious living spaces, and yield exceptional pride of ownership. Lavish with amenities, including three fireplaces, Viking chef’s kitchen, and a cherry-panelled elevator, it is set on tastefully landscaped grounds of nearly an acre, with ample room for a large pool and tennis. Come home soon!

1680 Lands End Road, Orient

$1,900,000

Welcome to this brand-new coastal retreat that epitomizes North Fork luxury. This exquisite property offers 4,500 square feet of meticulously designed living space across three levels, including a full walkout basement. This home seamlessly blends upscale entertaining with relaxed everyday living. Stroll outside to your private oasis, where a 20 x 40 heated, saltwater inground pool is the focal point, surrounded by an expansive patio, cozy fire pit, and lush landscaping. The 500 square-foot pool house enhances the outdoor experience with a wet bar, half bath, covered patio, and outdoor shower-ideal for rinsing off after enjoying your deeded Peconic Bay beach rights, located just moments away. Inside, high ceilings and open living spaces create a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, while the 5 spa-inspired bathrooms and 4 generous bedrooms offer comfort and style. The walkout lower level provides versatile space, perfect for a home theater, gym, or guest suite. An attached two-car garage offers convenience and ample storage for beach or golf gear. Situated in the coveted Cleaves Point Community, this property is just one minute from the beautiful Islands End Golf Course and three minutes from historic Greenport Village. This location combines coastal serenity with village convenience, making it an ideal full-time residence or luxurious weekend escape. This rare North Fork find is now available for sale, offering a unique opportunity to own a piece of paradise in one of New York's most sought-after locations. Could be You!

4 Beds ⋅ 5 Baths ⋅ 915141 MLS

Welcome to this brand-new coastal retreat that epitomizes North Fork luxury. This exquisite property offers 4,500 square feet of meticulously designed living space across three levels, including a full walkout basement. This home seamlessly blends upscale entertaining with relaxed everyday living. Stroll outside to your private oasis, where a 20 x 40 heated, saltwater inground pool is the focal point, surrounded by an expansive patio, cozy fire pit, and lush landscaping. The 500 square-foot pool house enhances the outdoor experience with a wet bar, half bath, covered patio, and outdoor shower-ideal for rinsing off after enjoying your deeded Peconic Bay beach rights, located just moments away. Inside, high ceilings and open living spaces create a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, while the 5 spa-inspired bathrooms and 4 generous bedrooms offer comfort and style. The walkout lower level provides versatile space, perfect for a home theater, gym, or guest suite. An attached two-car garage offers convenience and ample storage for beach or golf gear. Situated in the coveted Cleaves Point Community, this property is just one minute from the beautiful Islands End Golf Course and three minutes from historic Greenport Village. This location combines coastal serenity with village convenience, making it an ideal full-time residence or luxurious weekend escape. This rare North Fork find is now available for sale, offering a unique opportunity to own a piece of paradise in one of New York's most sought-after locations. Could be You!

435 Maple Lane, Greenport

$1,838,000

Beautifully updated & fully renovated in 2020, Arts & Crafts style home in the heart of Orient Village, one block from Orient Harbor, walking distance to post office, country store & all village amenities. Open concept dining/living room with large wood burning fireplace. Updated gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher, & wine cooler. Enclosed front porch sunroom. Second floor master bedroom with large balcony overlooking the garden with ensuite bath – 2 sinks, free-standing tub & walk-in shower. Two additional bedrooms and full bath with tub and front-loading washer/dryer. Fenced yard, outdoor shower, backyard deck & lower patio for outdoor dining & entertaining. Professionally landscaped with mature trees and flower beds. Detached 1-car garage.

3 Beds ⋅ 3 Baths ⋅ 981804 MLS

Beautifully updated & fully renovated in 2020, Arts & Crafts style home in the heart of Orient Village, one block from Orient Harbor, walking distance to post office, country store & all village amenities. Open concept dining/living room with large wood burning fireplace. Updated gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher, & wine cooler. Enclosed front porch sunroom. Second floor master bedroom with large balcony overlooking the garden with ensuite bath – 2 sinks, free-standing tub & walk-in shower. Two additional bedrooms and full bath with tub and front-loading washer/dryer. Fenced yard, outdoor shower, backyard deck & lower patio for outdoor dining & entertaining. Professionally landscaped with mature trees and flower beds. Detached 1-car garage.

1125 Navy Street, Orient

$1,825,000

Luxury new construction set on approximately one acre in the heart of East Marion, built by a renowned local builder known for exceptional craftsmanship and attention to detail. Welcome to 2045 Willow Drive, a beautifully appointed 4 bedroom, 4.5 bath residence offering refined design and modern comfort throughout. The chef’s kitchen features custom cabinetry, quartz countertops, stainless steel appliances, and designer lighting, seamlessly opening to the main living area anchored by a gas fireplace, ideal for both everyday living and entertaining. Generously sized bedroom suites provide comfort and privacy for residents and guests alike.  The semi-finished lower level offers approximately 1,500 additional square feet with 9-foot ceilings, an egress window, and electric with high-hat lighting already in place, presenting exceptional potential for future customization.  Outdoor living is elevated by a heated, saltwater in-ground pool with beige marble coping and patio area. The expansive backyard provides ample space for a future pool house, outdoor kitchen, or additional amenities. Additional highlights include a spacious two-car garage, stone driveway with extra parking, and strong curb appeal.  Ideally located near local beaches, farm stands, vineyards, and dining, this property offers the best of North Fork living in a private, one-acre setting with low taxes.

4 Beds ⋅ 5 Baths ⋅ 966205 MLS

Luxury new construction set on approximately one acre in the heart of East Marion, built by a renowned local builder known for exceptional craftsmanship and attention to detail. Welcome to 2045 Willow Drive, a beautifully appointed 4 bedroom, 4.5 bath residence offering refined design and modern comfort throughout. The chef’s kitchen features custom cabinetry, quartz countertops, stainless steel appliances, and designer lighting, seamlessly opening to the main living area anchored by a gas fireplace, ideal for both everyday living and entertaining. Generously sized bedroom suites provide comfort and privacy for residents and guests alike.  The semi-finished lower level offers approximately 1,500 additional square feet with 9-foot ceilings, an egress window, and electric with high-hat lighting already in place, presenting exceptional potential for future customization.  Outdoor living is elevated by a heated, saltwater in-ground pool with beige marble coping and patio area. The expansive backyard provides ample space for a future pool house, outdoor kitchen, or additional amenities. Additional highlights include a spacious two-car garage, stone driveway with extra parking, and strong curb appeal.  Ideally located near local beaches, farm stands, vineyards, and dining, this property offers the best of North Fork living in a private, one-acre setting with low taxes.

2045 Willow Drive, East Marion

$1,800,000

STYLISH & TRANQUIL: This designer's own home overlooks protected wetlands with panoramic views towards Orient Harbor and Hallocks Bay. The interior and exterior are repleat with custom architectural details. Ground floor open plan with living room, dining room and gourmet kitchen boasting Viking range, Sub Zero fridge and Bosch dishwasher. Imported terra cotta tile floors throughout, tumbled marble countertops. Rais wood burning stove ties the space together with flame view window. Also on ground floor, 2 bedrooms, 1.5 baths, mud room, ample screened in porch and extensive exterior decking. Upstairs primary bedroom with ensuite bath & dressing, additional bedroom/office and 2 working art/craft maker spaces with great natural light and access to back yard stairs to gunite, heated, salt water pool with bluestone patio and coping, outdoor shower & dining areas. Attached 2 car garage, whole house generator, full irrigation system. Very private fully fenced back yard. Wrap around cedar deck. Very close to Potato Dock & Orient Harbor beaches as well as all that Orient Village has to offer.

4 Beds ⋅ 3 Baths ⋅ 844387 MLS

STYLISH & TRANQUIL: This designer's own home overlooks protected wetlands with panoramic views towards Orient Harbor and Hallocks Bay. The interior and exterior are repleat with custom architectural details. Ground floor open plan with living room, dining room and gourmet kitchen boasting Viking range, Sub Zero fridge and Bosch dishwasher. Imported terra cotta tile floors throughout, tumbled marble countertops. Rais wood burning stove ties the space together with flame view window. Also on ground floor, 2 bedrooms, 1.5 baths, mud room, ample screened in porch and extensive exterior decking. Upstairs primary bedroom with ensuite bath & dressing, additional bedroom/office and 2 working art/craft maker spaces with great natural light and access to back yard stairs to gunite, heated, salt water pool with bluestone patio and coping, outdoor shower & dining areas. Attached 2 car garage, whole house generator, full irrigation system. Very private fully fenced back yard. Wrap around cedar deck. Very close to Potato Dock & Orient Harbor beaches as well as all that Orient Village has to offer.

1075 Narrow River Road, Orient

$1,687,500

Experience the best of North Fork coastal living in this beautifully appointed 3-bedroom, 2.5-bath waterfront condo with breathtaking views of Peconic Bay and Shelter Island. Enjoy your morning coffee as the sun rises or set sail from your dock just steps from your door. With spacious, light-filled interiors, two fireplaces and seamless indoor-outdoor flow, this home is designed for effortless living and entertaining by the sea. A rare offering in a coveted location-just a few minutes from all that Greenport has to offer; boating, shopping, dining, tasting rooms, art and more!

3 Beds ⋅ 3 Baths ⋅ 862399 MLS

Experience the best of North Fork coastal living in this beautifully appointed 3-bedroom, 2.5-bath waterfront condo with breathtaking views of Peconic Bay and Shelter Island. Enjoy your morning coffee as the sun rises or set sail from your dock just steps from your door. With spacious, light-filled interiors, two fireplaces and seamless indoor-outdoor flow, this home is designed for effortless living and entertaining by the sea. A rare offering in a coveted location-just a few minutes from all that Greenport has to offer; boating, shopping, dining, tasting rooms, art and more!

131 6th Street Unit #G7, Greenport

$1,645,000

Okay, so I went to this house and it actually just works. You come in and there's this built in coat rack with cubbies for shoes (like finally, a spot for beach stuff). The first floor is totally open, living, dining, kitchen are all connected so everyone can hang out while you cook. Off the kitchen there's a deck set up for sitting and eating, and it looks right out to a cute backyard. The mudroom is clutch, storage cabinets, laundry, and a half bath, and a door straight outside. Plus there's a detached garage that's basically your beach gear locker, and the beach is literally a block away. It's just been completely renovated but still feels like Greenport Village, and with the low maintenance coastal siding, new windows, insulation, roof, furnace already done, we don't have to do any work. Also, you're like .3 miles to the shops, LIRR, Hampton Jitney and Shelter Island Ferry, so weekends are super easy for adventures. This is a Holiday Home that can work for us.

3 Beds ⋅ 3 Baths ⋅ 941986 MLS

Okay, so I went to this house and it actually just works. You come in and there's this built in coat rack with cubbies for shoes (like finally, a spot for beach stuff). The first floor is totally open, living, dining, kitchen are all connected so everyone can hang out while you cook. Off the kitchen there's a deck set up for sitting and eating, and it looks right out to a cute backyard. The mudroom is clutch, storage cabinets, laundry, and a half bath, and a door straight outside. Plus there's a detached garage that's basically your beach gear locker, and the beach is literally a block away. It's just been completely renovated but still feels like Greenport Village, and with the low maintenance coastal siding, new windows, insulation, roof, furnace already done, we don't have to do any work. Also, you're like .3 miles to the shops, LIRR, Hampton Jitney and Shelter Island Ferry, so weekends are super easy for adventures. This is a Holiday Home that can work for us.

426 Clark Street, Greenport

$1,600,000

Welcome to an exceptional waterfront includes 2 units, 2-bedroom, 2.5-bath luxury condo offering sweeping panoramic views of Greenport Harbor and Stirling Basin. Located in one of Greenport’s most sought-after luxury buildings, this rare residence includes your own private boat slip and delivers an unmatched North Fork lifestyle. The home features a chef’s kitchen outfitted with state-of-the-art stainless steel appliances, an integrated refrigerator and dishwasher, and a built-in wine cooler. The open-concept kitchen, dining, and living area is designed for effortless entertaining, enhanced by soaring high ceilings and dramatic double doors that open onto a wrap-around balcony with breathtaking water views. Sunlight pours in throughout the day, brightening the entire space and framing breathtaking panoramic water views. The spacious primary suite is a private retreat, complete with balcony access, a custom walk-in closet with built-ins, and a spa-like en suite bath. A well-appointed second bedroom and additional full bath provide comfort and privacy for guests, while a convenient half bath serves the main living area. A unique bonus space adds incredible flexibility and can be used as an entertainment lounge, office, storage area, or private retreat — a rare feature that sets this unit apart. Additional highlights include in-unit laundry, dedicated indoor parking, and an additional outdoor parking space. Whether enjoying sunrise coffee on the balcony, docking your boat steps from home, or entertaining with harbor views as your backdrop, this residence captures the very best of waterfront living in the heart of Greenport.

2 Beds ⋅ 3 Baths ⋅ 961095 MLS

Welcome to an exceptional waterfront includes 2 units, 2-bedroom, 2.5-bath luxury condo offering sweeping panoramic views of Greenport Harbor and Stirling Basin. Located in one of Greenport’s most sought-after luxury buildings, this rare residence includes your own private boat slip and delivers an unmatched North Fork lifestyle. The home features a chef’s kitchen outfitted with state-of-the-art stainless steel appliances, an integrated refrigerator and dishwasher, and a built-in wine cooler. The open-concept kitchen, dining, and living area is designed for effortless entertaining, enhanced by soaring high ceilings and dramatic double doors that open onto a wrap-around balcony with breathtaking water views. Sunlight pours in throughout the day, brightening the entire space and framing breathtaking panoramic water views. The spacious primary suite is a private retreat, complete with balcony access, a custom walk-in closet with built-ins, and a spa-like en suite bath. A well-appointed second bedroom and additional full bath provide comfort and privacy for guests, while a convenient half bath serves the main living area. A unique bonus space adds incredible flexibility and can be used as an entertainment lounge, office, storage area, or private retreat — a rare feature that sets this unit apart. Additional highlights include in-unit laundry, dedicated indoor parking, and an additional outdoor parking space. Whether enjoying sunrise coffee on the balcony, docking your boat steps from home, or entertaining with harbor views as your backdrop, this residence captures the very best of waterfront living in the heart of Greenport.

123 Sterling Avenue Unit #4, Greenport

$1,500,000

Beautifully maintained 4 bedroom, 3 bath home in Pebble Beach Farms, located in the charming Hamlet of East Marion on the North Fork. Vaulted ceiling and walls of windows fill the open floor plan with natural light, creating a bright airy living space that captures the relaxed coastal lifestyle. Privately set with lush landscaping, the property features a spacious deck and backyard pool, ideal for summer entertaining or quiet weekend escapes. Residents enjoy access to a private beach, tennis, basketball & bocce courts. Just minutes to Greenport Village, renowned restaurants, wineries, and the ferry to Shelter Island and Sag Harbor – an ideal North Fork weekend escape or year-round retreat.

4 Beds ⋅ 3 Baths ⋅ 969328 MLS

Beautifully maintained 4 bedroom, 3 bath home in Pebble Beach Farms, located in the charming Hamlet of East Marion on the North Fork. Vaulted ceiling and walls of windows fill the open floor plan with natural light, creating a bright airy living space that captures the relaxed coastal lifestyle. Privately set with lush landscaping, the property features a spacious deck and backyard pool, ideal for summer entertaining or quiet weekend escapes. Residents enjoy access to a private beach, tennis, basketball & bocce courts. Just minutes to Greenport Village, renowned restaurants, wineries, and the ferry to Shelter Island and Sag Harbor – an ideal North Fork weekend escape or year-round retreat.

980 The Greenway, East Marion

$1,475,000

Stunning Greenport New Construction Colonial w/ Heated In-ground pool! Step into a seamless blend of turn-of-the-century elegance and contemporary comfort in this exquisite new construction Colonial. Designed with classic architectural details and high-end finishes throughout, this 4-bedroom, 4.5-bathroom residence offers 2,900 sq. ft. of thoughtfully crafted living space and includes a 10x20 heated in-ground salt water pool. From the moment you arrive, the crushed stone driveway and detached 1-car garage set the tone for the timeless appeal of this home. Inside, you’ll find gleaming hardwood floors throughout, complemented by custom millwork that adds warmth and character to every room. The open floor plan is anchored by a spacious Great Room with a stately fireplace, creating a cozy yet sophisticated gathering space. The gourmet kitchen opens effortlessly to the dining and living areas, ideal for entertaining. The main-level primary suite is a serene retreat, featuring a spa-like en-suite bathroom and ample closet space. A charming laundry/mudroom with custom red brick flooring offers both function and style. Downstairs, the fully finished basement expands the living space with a second fireplace, a wet bar, a full bathroom, and a dedicated media room—perfect for movie nights or game-day entertaining. Enjoy outdoor living on the poolside private patio, ideal for morning coffee or summer barbecues. Every inch of this home reflects a perfect balance of traditional craftsmanship and modern convenience. A rare opportunity to own a new home with historic character in every detail that is in close proximity to Greenport Village, walk to 67 Steps Beach along the LI Sound and direct access to all that the North Fork has to offer!

4 Beds ⋅ 5 Baths ⋅ 880117 MLS

Stunning Greenport New Construction Colonial w/ Heated In-ground pool! Step into a seamless blend of turn-of-the-century elegance and contemporary comfort in this exquisite new construction Colonial. Designed with classic architectural details and high-end finishes throughout, this 4-bedroom, 4.5-bathroom residence offers 2,900 sq. ft. of thoughtfully crafted living space and includes a 10x20 heated in-ground salt water pool. From the moment you arrive, the crushed stone driveway and detached 1-car garage set the tone for the timeless appeal of this home. Inside, you’ll find gleaming hardwood floors throughout, complemented by custom millwork that adds warmth and character to every room. The open floor plan is anchored by a spacious Great Room with a stately fireplace, creating a cozy yet sophisticated gathering space. The gourmet kitchen opens effortlessly to the dining and living areas, ideal for entertaining. The main-level primary suite is a serene retreat, featuring a spa-like en-suite bathroom and ample closet space. A charming laundry/mudroom with custom red brick flooring offers both function and style. Downstairs, the fully finished basement expands the living space with a second fireplace, a wet bar, a full bathroom, and a dedicated media room—perfect for movie nights or game-day entertaining. Enjoy outdoor living on the poolside private patio, ideal for morning coffee or summer barbecues. Every inch of this home reflects a perfect balance of traditional craftsmanship and modern convenience. A rare opportunity to own a new home with historic character in every detail that is in close proximity to Greenport Village, walk to 67 Steps Beach along the LI Sound and direct access to all that the North Fork has to offer!

130 Sunset Lane, Greenport

$1,470,000

Welcome to 155 Bridge St, a custom-built stunner within walking distance to Greenport Village’s thriving water-front district and close proximity to North Fork farm-stands and world renown beaches. This well-appointed and thoughtfully designed home is truly turnkey, offering everything you could ask for and more. The open floor plan great-room is airy and flush with natural light, compliments of high-vaulted ceilings in the kitchen and perfectly balanced by the wide plank white oak floors throughout. As you walk-through the home, you’ll admire custom mill work, built-in shelving, a gas fireplace anchoring the first-floor great room and chic finishes that were perfectly selected and executed. The main level offers a convenient first floor en-suite bedroom, while the second floor features a generously sized primary bedroom with private en-suite bathroom and 2 additional guest bedrooms sharing a full hallway bathroom. The lower level provides a huge bonus with a second living-room/media room, conveniently located 1/2 bathroom, dry bar, laundry room, fifth bedroom, utility room for storage and owner’s closets. Finally, the rear yard provides a private resort-like experience with its bluestone patio, 10x20 heated saltwater pool, 8-foot high hedges and outdoor shower. This offering boasts outstanding rental history over the last five years, plus the option of coming fully furnished (down to the pool floats!), making this an ideal turnkey investment as well as your East End retreat!

5 Beds ⋅ 4 Baths ⋅ 969483 MLS

Welcome to 155 Bridge St, a custom-built stunner within walking distance to Greenport Village’s thriving water-front district and close proximity to North Fork farm-stands and world renown beaches. This well-appointed and thoughtfully designed home is truly turnkey, offering everything you could ask for and more. The open floor plan great-room is airy and flush with natural light, compliments of high-vaulted ceilings in the kitchen and perfectly balanced by the wide plank white oak floors throughout. As you walk-through the home, you’ll admire custom mill work, built-in shelving, a gas fireplace anchoring the first-floor great room and chic finishes that were perfectly selected and executed. The main level offers a convenient first floor en-suite bedroom, while the second floor features a generously sized primary bedroom with private en-suite bathroom and 2 additional guest bedrooms sharing a full hallway bathroom. The lower level provides a huge bonus with a second living-room/media room, conveniently located 1/2 bathroom, dry bar, laundry room, fifth bedroom, utility room for storage and owner’s closets. Finally, the rear yard provides a private resort-like experience with its bluestone patio, 10x20 heated saltwater pool, 8-foot high hedges and outdoor shower. This offering boasts outstanding rental history over the last five years, plus the option of coming fully furnished (down to the pool floats!), making this an ideal turnkey investment as well as your East End retreat!

155 Bridge Street, Greenport

$1,450,000

Orient By The Sea — Sound front community with a deeded association beach and park. Two story, 4 bedroom, 3 1/2 bathroom Nantucket style residence in sought-after Orient By-The-Sea. Perfect for year-round or vacation living. Covered mahogany wrap porch welcomes you to this light, open and spacious home that is perfect for entertaining, holiday gatherings, and cozy family time. Living room, great room, formal dining room, large kitchen with informal dining area. Wooden floors, light-filled. Great room has a vaulted ceiling and floor to ceiling gas stone fireplace and hearth, huge windows and transoms. Great room opens to gracious rear covered porch with ceiling fan and skylights, providing shade and "cover" while also permitting natural light. Great room, kitchen, and porch overlook the gorgeous level rear yard. This home features two spacious primary ensuite bedrooms, one on the main level and a second primary ensuite on the second level. A laundry room and powder room complete the main floor. A balcony walkway overlooks the great room from the second floor. Primary ensuite, two additional bedrooms and a full hall bathroom with an additional bonus space with windows and skylights complete the second floor. Attached two-car garage. The level shy acre property offers a serene, private landscape of lawn, mature specimen plantings and plenty of room for a swimming pool. The Cross Sound Ferry, Orient State Park, and Duryea's Restaurant are close by. The beautiful, well-maintained association sound beach, with a stone path, picnic area, and brick barbecue is just around the corner. A very special opportunity to live and enjoy life on the North Fork, from a coveted Orient location.

4 Beds ⋅ 4 Baths ⋅ 932673 MLS

Orient By The Sea — Sound front community with a deeded association beach and park. Two story, 4 bedroom, 3 1/2 bathroom Nantucket style residence in sought-after Orient By-The-Sea. Perfect for year-round or vacation living. Covered mahogany wrap porch welcomes you to this light, open and spacious home that is perfect for entertaining, holiday gatherings, and cozy family time. Living room, great room, formal dining room, large kitchen with informal dining area. Wooden floors, light-filled. Great room has a vaulted ceiling and floor to ceiling gas stone fireplace and hearth, huge windows and transoms. Great room opens to gracious rear covered porch with ceiling fan and skylights, providing shade and "cover" while also permitting natural light. Great room, kitchen, and porch overlook the gorgeous level rear yard. This home features two spacious primary ensuite bedrooms, one on the main level and a second primary ensuite on the second level. A laundry room and powder room complete the main floor. A balcony walkway overlooks the great room from the second floor. Primary ensuite, two additional bedrooms and a full hall bathroom with an additional bonus space with windows and skylights complete the second floor. Attached two-car garage. The level shy acre property offers a serene, private landscape of lawn, mature specimen plantings and plenty of room for a swimming pool. The Cross Sound Ferry, Orient State Park, and Duryea's Restaurant are close by. The beautiful, well-maintained association sound beach, with a stone path, picnic area, and brick barbecue is just around the corner. A very special opportunity to live and enjoy life on the North Fork, from a coveted Orient location.

815 Uhl Lane, Orient

$1,450,000

This beautiful custom built 2 story home is located minutes from a deeded beach and downtown Greenport with shops, wineries, boating, and golf. This classic style home blends style and comfort. Features include first floor primary bedroom with its own full bathroom and walk in closet, chef's style eat in kitchen with sub zero fridge, Jenn Air oven, and center island, wide plank flooring, living room that shares a two sided gas fireplace with the den, sun filled sunroom/dining room, laundry room, and half bathroom. The second floor features 3 bedrooms, one of which is huge and could be used for entertaining, and a full bathroom. The home has a full basement with an inside and outside entrance. Extras include a generator, central vac, central a/c, and rear patio.

4 Beds ⋅ 3 Baths ⋅ 899283 MLS

This beautiful custom built 2 story home is located minutes from a deeded beach and downtown Greenport with shops, wineries, boating, and golf. This classic style home blends style and comfort. Features include first floor primary bedroom with its own full bathroom and walk in closet, chef's style eat in kitchen with sub zero fridge, Jenn Air oven, and center island, wide plank flooring, living room that shares a two sided gas fireplace with the den, sun filled sunroom/dining room, laundry room, and half bathroom. The second floor features 3 bedrooms, one of which is huge and could be used for entertaining, and a full bathroom. The home has a full basement with an inside and outside entrance. Extras include a generator, central vac, central a/c, and rear patio.

1000 Green Hill Lane, Greenport

$1,415,000

Welcome to 619 Bailey Avenue, a fully restored and move-in ready farmhouse located on the fringe of Greenport Village. Originally part of a larger North Fork farm and estate, this incredibly well appointed circa 1900 residence has been thoughtfully re-imagined to blend modern conveniences with preserved period details. Original features such as hardwood floors, detailed millwork/moldings, and classic architectural elements have been carefully maintained, while updates throughout provide comfort and functionality. The custom kitchen is a standout, featuring a 48" range, oversized center island, custom cabinetry, and an 8-foot bi-fold glass door that opens to the rear yard, creating seamless indoor-outdoor living. The first floor offers a well-balanced layout with a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, the second level includes two guest bedrooms and a full hallway bath, along with a primary suite featuring vaulted ceilings, a large walk-in closet, and an en-suite bathroom with double vanity and a walk-in shower with a dual shower head system. The rear yard is expansive and private, complemented by a detached one-car garage. Not to mention, there is also an active permit in place for a 16' x 32' in-ground pool, a perfect opportunity to take this rare offering one step further. Conveniently located near Greenport Village's business district, Kontokosta Vineyard, Bay/Sound Beaches and Sep's Farm-stand, this amazing offering is sure not to last!

4 Beds ⋅ 3 Baths ⋅ 990609 MLS

Welcome to 619 Bailey Avenue, a fully restored and move-in ready farmhouse located on the fringe of Greenport Village. Originally part of a larger North Fork farm and estate, this incredibly well appointed circa 1900 residence has been thoughtfully re-imagined to blend modern conveniences with preserved period details. Original features such as hardwood floors, detailed millwork/moldings, and classic architectural elements have been carefully maintained, while updates throughout provide comfort and functionality. The custom kitchen is a standout, featuring a 48" range, oversized center island, custom cabinetry, and an 8-foot bi-fold glass door that opens to the rear yard, creating seamless indoor-outdoor living. The first floor offers a well-balanced layout with a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, the second level includes two guest bedrooms and a full hallway bath, along with a primary suite featuring vaulted ceilings, a large walk-in closet, and an en-suite bathroom with double vanity and a walk-in shower with a dual shower head system. The rear yard is expansive and private, complemented by a detached one-car garage. Not to mention, there is also an active permit in place for a 16' x 32' in-ground pool, a perfect opportunity to take this rare offering one step further. Conveniently located near Greenport Village's business district, Kontokosta Vineyard, Bay/Sound Beaches and Sep's Farm-stand, this amazing offering is sure not to last!

619 Bailey Avenue, Greenport

2460 Shipyard Lane Unit #5E, East Marion

$1,350,000

Fully remodeled condo in the sought-after Cleves Point Club & Marina community of East Marion. Thoughtfully designed to maximize flow and highlight the stunning water views, this home features stylish, up-to-date renovations throughout. Primary ensuite bedroom with waterside deck and ample closet space. There is a loft for an additional bedroom and bath if needed. Home also includes a full basement and 2 washers and 2 dryers (upstairs and downstairs). Living room with sliders to back deck overlooking the water and marina. Other features include, full wet bar with a wine fridge, separate sink and, an ice maker. Not a single detail was missed while renovating the home. The community offers resort-like amenities, including tennis courts, a pickleball court, pool, fitness center, and private docking for boats. Just moments away from the charming village of Greenport, you'll enjoy easy access to boutique shopping, world-class dining, and vibrant local culture. This is more than a home-it's a lifestyle. Whether as a full-time residence or a North Fork retreat, this property delivers the perfect balance of luxury, convenience, and coastal charm.

2 Beds ⋅ 3 Baths ⋅ 901327 MLS

Fully remodeled condo in the sought-after Cleves Point Club & Marina community of East Marion. Thoughtfully designed to maximize flow and highlight the stunning water views, this home features stylish, up-to-date renovations throughout. Primary ensuite bedroom with waterside deck and ample closet space. There is a loft for an additional bedroom and bath if needed. Home also includes a full basement and 2 washers and 2 dryers (upstairs and downstairs). Living room with sliders to back deck overlooking the water and marina. Other features include, full wet bar with a wine fridge, separate sink and, an ice maker. Not a single detail was missed while renovating the home. The community offers resort-like amenities, including tennis courts, a pickleball court, pool, fitness center, and private docking for boats. Just moments away from the charming village of Greenport, you'll enjoy easy access to boutique shopping, world-class dining, and vibrant local culture. This is more than a home-it's a lifestyle. Whether as a full-time residence or a North Fork retreat, this property delivers the perfect balance of luxury, convenience, and coastal charm.

2460 Shipyard Lane Unit #5E, East Marion

$1,330,000

Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 8 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan. Additional information: Appearance: New.

3 Beds ⋅ 3 Baths ⋅ 813226 MLS

Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 8 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan. Additional information: Appearance: New.

123 Sterling Avenue Unit #8, Greenport

$1,300,000

This c.1890 Greenport Village gem boasts 3 bedrooms, 2.5 baths plus a detached studio apartment. Set in the heart of the historic district, it merges many distinctive original details with thoughtful modern updates. A beautifully planted enclosed rear garden with deck and patio, perfect for relaxing and entertaining, leads to a renovated barn which features a 2-car garage and the spacious studio apartment. The main residence's generous ground floor living spaces include a front parlor and living room with original pocket doors, dining room, powder room, and a large renovated kitchen centered on a 48" Capital gas range. Upstairs there are three bedrooms and two full bathrooms, including one en suite. Refinished original wood floors add warmth and character throughout. The restaurants, shops and waterfront of the maritime village are just a few blocks away from this refined and peaceful retreat.

3 Beds ⋅ 4 Baths ⋅ 861088 MLS

This c.1890 Greenport Village gem boasts 3 bedrooms, 2.5 baths plus a detached studio apartment. Set in the heart of the historic district, it merges many distinctive original details with thoughtful modern updates. A beautifully planted enclosed rear garden with deck and patio, perfect for relaxing and entertaining, leads to a renovated barn which features a 2-car garage and the spacious studio apartment. The main residence's generous ground floor living spaces include a front parlor and living room with original pocket doors, dining room, powder room, and a large renovated kitchen centered on a 48" Capital gas range. Upstairs there are three bedrooms and two full bathrooms, including one en suite. Refinished original wood floors add warmth and character throughout. The restaurants, shops and waterfront of the maritime village are just a few blocks away from this refined and peaceful retreat.

604 Main Street, Greenport

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