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"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

$2,150,000

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

$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

$1,600,000

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

$1,475,000

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

$1,415,000

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

$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

$1,294,000

Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

3 Beds ⋅ 3 Baths ⋅ 950921 MLS

Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

55 Brown Street, Greenport

$1,215,000

Some houses get a coat of paint and call it a day, 611 aka 175 Maple Street got a full designer renovation! This charming house is just a short stroll from Greenport Village waterfront restaurants, boutiques & beaches. This home delivers the warmth of classic architecture with a modern flair. Enter through the front door and the character hits first: hardwood floors throughout, recessed lighting overhead, and high-end finishes that make every room feel curated rather than constructed. The first floor flows easily between a thoughtfully designed living space and a kitchen equipped with stainless steel high end appliances and clean lines. Enjoy a cozy sun-room overlooking the backyard and a bonus space off the kitchen, which could have many uses including an office or flex space. Up-stairs, the entire second floor is dedicated to a spacious primary suite removed from the rest of the home in the best way possible! The primary suite spans the full upper level...a genuine retreat with vaulted ceilings with wood beams and its own en-suite bathroom including radiant heat in the floors and designer finishes. Two additional bedrooms on the main floor keep family and guests comfortable without compromise. Outside, the transformation continues. Bluestone pavers trace the front walkway and wrap the back patio. There is a detached cedar shake garage that is also freshly renovated. The ample driveway, which is crushed natural stone handles guests effortlessly- a rare feature for Greenport! Every system, the electric, plumbing, HVAC is brand new. Truly a turnkey getaway in one of the best locations in Greenport!

3 Beds ⋅ 2 Baths ⋅ 999868 MLS

Some houses get a coat of paint and call it a day, 611 aka 175 Maple Street got a full designer renovation! This charming house is just a short stroll from Greenport Village waterfront restaurants, boutiques & beaches. This home delivers the warmth of classic architecture with a modern flair. Enter through the front door and the character hits first: hardwood floors throughout, recessed lighting overhead, and high-end finishes that make every room feel curated rather than constructed. The first floor flows easily between a thoughtfully designed living space and a kitchen equipped with stainless steel high end appliances and clean lines. Enjoy a cozy sun-room overlooking the backyard and a bonus space off the kitchen, which could have many uses including an office or flex space. Up-stairs, the entire second floor is dedicated to a spacious primary suite removed from the rest of the home in the best way possible! The primary suite spans the full upper level...a genuine retreat with vaulted ceilings with wood beams and its own en-suite bathroom including radiant heat in the floors and designer finishes. Two additional bedrooms on the main floor keep family and guests comfortable without compromise. Outside, the transformation continues. Bluestone pavers trace the front walkway and wrap the back patio. There is a detached cedar shake garage that is also freshly renovated. The ample driveway, which is crushed natural stone handles guests effortlessly- a rare feature for Greenport! Every system, the electric, plumbing, HVAC is brand new. Truly a turnkey getaway in one of the best locations in Greenport!

175 AKA 611 Maple Street, Greenport

$1,100,000

Newly Reduced Price! Welcome to 145 Osprey Nest Road, a gem nestled in the heart of the charming Cleaves Point Beach Community. This home, with its resort-like atmosphere, offers an enticing blend of comfort and convenience. As a member of the Community, this property affords use of a private Bay Beach, in addition to having a community marina with some private docks and mooring lots, in a protected inlet off the Peconic Bay. This spacious home boasts four bedrooms and three bathrooms, designed with a modern aesthetic and an open, airy layout. The primary suite offers a private retreat, while three additional guest bedrooms share a full bath. The home's generous windows and soaring ceiling heights invite an abundance of natural light, creating a warm and inviting atmosphere. The home's living spaces are equally impressive. A cozy family room, a formal living room, and a dining area that flows into an eat-in kitchen, provide ample space for entertaining or relaxing. A wood-burning fireplace adds a touch of rustic charm, and a conveniently located full bath off the kitchen houses a washer/dryer for easy laundry days. The property's exterior is equally impressive. It sits on a generous 1/3 acre corner lot, surrounded by mature hedges for added privacy. The large mahogany deck, with a built-in Endless Pool Swim Spa, is the perfect place to relax and soak in the sun. Before returning indoors, the adjacent outdoor shower is available for your use. Just a stone's throw away, you'll find the bustling Village of Greenport, home to boutique shops, top-rated restaurants, and the Greenport marina in Mitchell Park. The nearby Island’s End Golf & Country Club, vineyards, farms, and beaches, along with the Orient Beach State Park, offer a plethora of leisure activities. 145 Osprey Nest Road is more than just a home; it's a lifestyle. Experience the best of coastal living in a community that welcomes everyone. Don't miss out on this opportunity. Schedule your viewing today!

4 Beds ⋅ 3 Baths ⋅ 990436 MLS

Newly Reduced Price! Welcome to 145 Osprey Nest Road, a gem nestled in the heart of the charming Cleaves Point Beach Community. This home, with its resort-like atmosphere, offers an enticing blend of comfort and convenience. As a member of the Community, this property affords use of a private Bay Beach, in addition to having a community marina with some private docks and mooring lots, in a protected inlet off the Peconic Bay. This spacious home boasts four bedrooms and three bathrooms, designed with a modern aesthetic and an open, airy layout. The primary suite offers a private retreat, while three additional guest bedrooms share a full bath. The home's generous windows and soaring ceiling heights invite an abundance of natural light, creating a warm and inviting atmosphere. The home's living spaces are equally impressive. A cozy family room, a formal living room, and a dining area that flows into an eat-in kitchen, provide ample space for entertaining or relaxing. A wood-burning fireplace adds a touch of rustic charm, and a conveniently located full bath off the kitchen houses a washer/dryer for easy laundry days. The property's exterior is equally impressive. It sits on a generous 1/3 acre corner lot, surrounded by mature hedges for added privacy. The large mahogany deck, with a built-in Endless Pool Swim Spa, is the perfect place to relax and soak in the sun. Before returning indoors, the adjacent outdoor shower is available for your use. Just a stone's throw away, you'll find the bustling Village of Greenport, home to boutique shops, top-rated restaurants, and the Greenport marina in Mitchell Park. The nearby Island’s End Golf & Country Club, vineyards, farms, and beaches, along with the Orient Beach State Park, offer a plethora of leisure activities. 145 Osprey Nest Road is more than just a home; it's a lifestyle. Experience the best of coastal living in a community that welcomes everyone. Don't miss out on this opportunity. Schedule your viewing today!

145 Osprey Nest Road, Greenport

$1,075,000

Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport.

3 Beds ⋅ 2 Baths ⋅ 1021578 MLS

Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport.

217 Center Street, Greenport

$1,050,000

Welcome to this charming abode. This beautiful residence features three spacious bedrooms and two well-appointed bathrooms, perfect for comfortable living. The house is thoughtfully designed with additional features that add to its allure. Hard wood floors throughout. Buckets of room for a pool on this shy acre. Nestled in the heart of Greenport, the community environment is vibrant and welcoming. The area boasts of various local amenities, including parks, shopping centers, and eateries, ensuring a balanced and enjoyable lifestyle. The property is in excellent condition, offering a blend of comfort and modernity. Its neutral palette and inclusive design make it an ideal choice for anyone looking for a peaceful retreat in the midst of a thriving community. Experience a unique blend of tranquility and convenience here at your North Fork retreat. This property is not just a house, but a place you can truly call home. Reserve your private showing today!

3 Beds ⋅ 2 Baths ⋅ 988365 MLS

Welcome to this charming abode. This beautiful residence features three spacious bedrooms and two well-appointed bathrooms, perfect for comfortable living. The house is thoughtfully designed with additional features that add to its allure. Hard wood floors throughout. Buckets of room for a pool on this shy acre. Nestled in the heart of Greenport, the community environment is vibrant and welcoming. The area boasts of various local amenities, including parks, shopping centers, and eateries, ensuring a balanced and enjoyable lifestyle. The property is in excellent condition, offering a blend of comfort and modernity. Its neutral palette and inclusive design make it an ideal choice for anyone looking for a peaceful retreat in the midst of a thriving community. Experience a unique blend of tranquility and convenience here at your North Fork retreat. This property is not just a house, but a place you can truly call home. Reserve your private showing today!

1105 August Lane, Greenport

$1,050,000

Opportunities like this in August Acres are few and far between. This 4-bedroom, 2.5-bath Colonial with deeded beach rights delivers the rare combination buyers wait for—location, efficiency, and long-term value—without compromise. From the moment you arrive, the home feels both welcoming and solid. A cozy fireplace anchors the main living space, while tilt-in Andersen windows fill the home with natural light and simplify maintenance. Behind the scenes, major investments have already been made: solar panels, a new roof, and central vacuum offer peace of mind and lower carrying costs—features buyers wish for but rarely find already done. The radiant-heated basement and garage elevate everyday living and future potential, providing comfort and flexibility that set this home apart from others in the neighborhood. Step outside to the bluestone patio, where summer evenings, entertaining, and quiet mornings become part of daily life. With beach access, meaningful upgrades, and a highly desirable neighborhood, this is the kind of home buyers regret missing. A rare chance to secure not just a property—but a lifestyle—in August Acres.

4 Beds ⋅ 3 Baths ⋅ 949504 MLS

Opportunities like this in August Acres are few and far between. This 4-bedroom, 2.5-bath Colonial with deeded beach rights delivers the rare combination buyers wait for—location, efficiency, and long-term value—without compromise. From the moment you arrive, the home feels both welcoming and solid. A cozy fireplace anchors the main living space, while tilt-in Andersen windows fill the home with natural light and simplify maintenance. Behind the scenes, major investments have already been made: solar panels, a new roof, and central vacuum offer peace of mind and lower carrying costs—features buyers wish for but rarely find already done. The radiant-heated basement and garage elevate everyday living and future potential, providing comfort and flexibility that set this home apart from others in the neighborhood. Step outside to the bluestone patio, where summer evenings, entertaining, and quiet mornings become part of daily life. With beach access, meaningful upgrades, and a highly desirable neighborhood, this is the kind of home buyers regret missing. A rare chance to secure not just a property—but a lifestyle—in August Acres.

1705 Kerwin Boulevard, Greenport

$1,050,000

A true gem in the heart of Greenport's charming maritime village! Charming 4-bedroom home on a picturesque tree-lined street with water glimpses as you go. This beautifully preserved home is full of character and charm, and ideally located just moments from the waterfront, dining, shops, convenient transportation, beaches and everything that makes Greenport village so special. This gem of a home has a welcoming front porch, inviting foyer/parlor, eat-in kitchen, formal dining room, spacious living room, full walk-up attic offering expansion potential or creative space, full basement for storage or workshop use, and a one car detached garage. Whether you're seeking a year-round residence, a weekend retreat, or a piece of Greenport's rich history, this property offers unmatched character and location.

4 Beds ⋅ 2 Baths ⋅ 912884 MLS

A true gem in the heart of Greenport's charming maritime village! Charming 4-bedroom home on a picturesque tree-lined street with water glimpses as you go. This beautifully preserved home is full of character and charm, and ideally located just moments from the waterfront, dining, shops, convenient transportation, beaches and everything that makes Greenport village so special. This gem of a home has a welcoming front porch, inviting foyer/parlor, eat-in kitchen, formal dining room, spacious living room, full walk-up attic offering expansion potential or creative space, full basement for storage or workshop use, and a one car detached garage. Whether you're seeking a year-round residence, a weekend retreat, or a piece of Greenport's rich history, this property offers unmatched character and location.

609 1st Street, Greenport

$999,999

Welcome to North Fork living at its finest! This beautifully maintained 3-bedroom 2 1/2-bath home offers the perfect blend of coastal charm and comfort, ideally located just moments from the golf course and with private beach access. Surrounded by stunning, professionally landscaped grounds, the property features an inviting deck and spacious patio-perfect for outdoor entertaining or relaxing in a peaceful setting. Inside you will find a layout designed for both everyday living and weekend getaways. Whether you're seeking a year-round residence or a serene retreat, this exceptional home captures the best of the North Fork lifestyle

3 Beds ⋅ 3 Baths ⋅ 1002141 MLS

Welcome to North Fork living at its finest! This beautifully maintained 3-bedroom 2 1/2-bath home offers the perfect blend of coastal charm and comfort, ideally located just moments from the golf course and with private beach access. Surrounded by stunning, professionally landscaped grounds, the property features an inviting deck and spacious patio-perfect for outdoor entertaining or relaxing in a peaceful setting. Inside you will find a layout designed for both everyday living and weekend getaways. Whether you're seeking a year-round residence or a serene retreat, this exceptional home captures the best of the North Fork lifestyle

450 Maple Lane, Greenport

$999,999

Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

4 Beds ⋅ 4 Baths ⋅ 960148 MLS

Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

285 Sandy Beach Road, Greenport

$999,000

CHIC. STYLISH. SOPHISTICATED. This Brooklyn Brownstone-inspired beauty brings big-city edge to North Fork living. 3 Beds | 3.5 Baths. Stunning new construction. Entertainer's dream kitchen. EV charging ready. Chic studio shed. Fenced + professionally landscaped backyard. Sun-drenched. Designer-finished. MINT+++. Stroll to farmers markets, restaurants, bars, boutiques, and the waterfront. This is Greenport living at its most irresistible.

3 Beds ⋅ 4 Baths ⋅ 961348 MLS

CHIC. STYLISH. SOPHISTICATED. This Brooklyn Brownstone-inspired beauty brings big-city edge to North Fork living. 3 Beds | 3.5 Baths. Stunning new construction. Entertainer's dream kitchen. EV charging ready. Chic studio shed. Fenced + professionally landscaped backyard. Sun-drenched. Designer-finished. MINT+++. Stroll to farmers markets, restaurants, bars, boutiques, and the waterfront. This is Greenport living at its most irresistible.

216 North Street, Greenport

$945,000

A unique opportunity set on 3.3 acres in the heart of Greenport. This two-bedroom residence was cleverly designed with future expansion in mind, while offering an easy-to-maintain home in its current form just minutes from the beach and Greenport’s commercial center. The house sits on a cleared 1.7-acre residential parcel with beautiful specimen trees and a vegetable garden, while the neighboring 1.6-acre wooded lot can be used for agriculture or preserved as a natural buffer to neighboring properties, providing exceptional privacy and a tranquil setting. Ideal for those envisioning a larger future project while still deriving immediate utility from the property, or for buyers seeking an easy Greenport pied-a-terre with acreage, privacy, and room to grow.

2 Beds ⋅ 1 Baths ⋅ 999762 MLS

A unique opportunity set on 3.3 acres in the heart of Greenport. This two-bedroom residence was cleverly designed with future expansion in mind, while offering an easy-to-maintain home in its current form just minutes from the beach and Greenport’s commercial center. The house sits on a cleared 1.7-acre residential parcel with beautiful specimen trees and a vegetable garden, while the neighboring 1.6-acre wooded lot can be used for agriculture or preserved as a natural buffer to neighboring properties, providing exceptional privacy and a tranquil setting. Ideal for those envisioning a larger future project while still deriving immediate utility from the property, or for buyers seeking an easy Greenport pied-a-terre with acreage, privacy, and room to grow.

427 Sound Road, Greenport

$940,000

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

3 Beds ⋅ 2 Baths ⋅ 956373 MLS

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

506 5th Street, Greenport

$927,500

Enjoy the best of North Fork living in Greenport’s sought-after August Acres community. This meticulously maintained 3-bedroom, 2-bath ranch sits on a shy acre, offering exceptional privacy and ample room to create your own backyard retreat — including space for a pool. Thoughtful updates enhance the home’s comfort and appeal, including fresh interior paint (2026), a new deck, an updated kitchen, and a new heating system. The spacious den, featuring a wood-burning fireplace and sliding doors to the deck, provides an inviting setting for relaxing or entertaining. Additional highlights include a primary en-suite with a generous bath and walk-in closet, a bright living room, dining area, convenient laundry room, full basement and a 2-car garage. Residents also enjoy access to the association’s deeded bay beach — the perfect spot to experience the beauty of North Fork living. This house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

3 Beds ⋅ 2 Baths ⋅ 1015877 MLS

Enjoy the best of North Fork living in Greenport’s sought-after August Acres community. This meticulously maintained 3-bedroom, 2-bath ranch sits on a shy acre, offering exceptional privacy and ample room to create your own backyard retreat — including space for a pool. Thoughtful updates enhance the home’s comfort and appeal, including fresh interior paint (2026), a new deck, an updated kitchen, and a new heating system. The spacious den, featuring a wood-burning fireplace and sliding doors to the deck, provides an inviting setting for relaxing or entertaining. Additional highlights include a primary en-suite with a generous bath and walk-in closet, a bright living room, dining area, convenient laundry room, full basement and a 2-car garage. Residents also enjoy access to the association’s deeded bay beach — the perfect spot to experience the beauty of North Fork living. This house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

2675 Kerwin Boulevard, Greenport

$899,000

Exquisitely renovated, this charming cedarshake Craftsman, in the seaport village of Greenport, is filled with light. From the airy front sunroom porch, to the spacious living room, formal dining room, and eat-in kitchen, this enchanting Arts & Crafts Cottage also boasts a huge primary ensuite bedroom with walk-in closet on the 2nd floor, another large bedroom on the first floor and two more flex rooms that can be used as offices, dens, or overspill guest bedrooms. The laundry room is on the first floor as is the 2nd full bathroom. A sweet and private backyard, edged with Privet, backs up to the one-car garage. This lovely property is across the street from the Greenport School with its playing fields and track and a short distance from the 6th Street Beach, Village shopping and restaurants, and the transportation hub where you can catch the train or Jitney to Manhattan or the ferry to Shelter Island & the South Fork.

3 Beds ⋅ 2 Baths ⋅ 957568 MLS

Exquisitely renovated, this charming cedarshake Craftsman, in the seaport village of Greenport, is filled with light. From the airy front sunroom porch, to the spacious living room, formal dining room, and eat-in kitchen, this enchanting Arts & Crafts Cottage also boasts a huge primary ensuite bedroom with walk-in closet on the 2nd floor, another large bedroom on the first floor and two more flex rooms that can be used as offices, dens, or overspill guest bedrooms. The laundry room is on the first floor as is the 2nd full bathroom. A sweet and private backyard, edged with Privet, backs up to the one-car garage. This lovely property is across the street from the Greenport School with its playing fields and track and a short distance from the 6th Street Beach, Village shopping and restaurants, and the transportation hub where you can catch the train or Jitney to Manhattan or the ferry to Shelter Island & the South Fork.

803 Front Street, Greenport

$860,000

Greenport Colonial Close To Village. This inviting Greenport Colonial offers 4 bedrooms and 3 full baths, blending comfort with a prime location. Set on a spacious lot, the home features a welcoming front yard, a fenced backyard with newly refinished hardwood floors, and a new deck-ideal for summer gatherings. Conveniently located close to Greenport Village, you’ll enjoy easy access to shops, restaurants, public transportation, golf, beaches, vineyards, breweries, the North Ferry, and local schools. Whether as a year-round residence or a seasonal getaway, this property provides the perfect balance of lifestyle, location, and leisure in the heart of the North Fork.

4 Beds ⋅ 3 Baths ⋅ 916687 MLS

Greenport Colonial Close To Village. This inviting Greenport Colonial offers 4 bedrooms and 3 full baths, blending comfort with a prime location. Set on a spacious lot, the home features a welcoming front yard, a fenced backyard with newly refinished hardwood floors, and a new deck-ideal for summer gatherings. Conveniently located close to Greenport Village, you’ll enjoy easy access to shops, restaurants, public transportation, golf, beaches, vineyards, breweries, the North Ferry, and local schools. Whether as a year-round residence or a seasonal getaway, this property provides the perfect balance of lifestyle, location, and leisure in the heart of the North Fork.

210 Bennet Road, Greenport

$850,000

Welcome to this charming Farmhouse/Colonial in one of Greenport’s most desirable in-town neighborhoods. Just moments from sandy beaches, award-winning restaurants, boutique shops, and the harbor, this home offers the perfect blend of village lifestyle and quiet residential living.Enjoy 4 bedrooms all privately set on the second level, including a spacious primary bedroom with a cozy loft. Sunlight fills the home through classic windows that complement the warmth of wood floors throughout. The inviting first floor features an eat-in kitchen with granite countertops, stainless steel appliances, and a pantry, along with the convenience of a first-floor laundry room. Step outside onto the Trex front porch or unwind on the Trex back deck overlooking the backyard — ideal for grilling and casual entertaining. Practical upgrades include 3-zone heating, a security system plus Ring camera, generator, newer hot water heater, and oil furnace. An attic above the addition offers excellent storage, and off-street parking accommodates 2–3 vehicles. Perfectly suited as a primary home, weekend retreat, or investment property, this Greenport gem puts the best of the North Fork right at your doorstep.

4 Beds ⋅ 3 Baths ⋅ 942474 MLS

Welcome to this charming Farmhouse/Colonial in one of Greenport’s most desirable in-town neighborhoods. Just moments from sandy beaches, award-winning restaurants, boutique shops, and the harbor, this home offers the perfect blend of village lifestyle and quiet residential living.Enjoy 4 bedrooms all privately set on the second level, including a spacious primary bedroom with a cozy loft. Sunlight fills the home through classic windows that complement the warmth of wood floors throughout. The inviting first floor features an eat-in kitchen with granite countertops, stainless steel appliances, and a pantry, along with the convenience of a first-floor laundry room. Step outside onto the Trex front porch or unwind on the Trex back deck overlooking the backyard — ideal for grilling and casual entertaining. Practical upgrades include 3-zone heating, a security system plus Ring camera, generator, newer hot water heater, and oil furnace. An attic above the addition offers excellent storage, and off-street parking accommodates 2–3 vehicles. Perfectly suited as a primary home, weekend retreat, or investment property, this Greenport gem puts the best of the North Fork right at your doorstep.

735 aka 718 Wiggins Street, Greenport

$849,000

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

2 Beds ⋅ 2 Baths ⋅ 995738 MLS

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

335 Sterling Place, Greenport

$800,000

Unique opportunity to own a Main Street Retail shop the heart of Historic Greenport. Built in the 1800s and full of charm and history.

921718 MLS

Unique opportunity to own a Main Street Retail shop the heart of Historic Greenport. Built in the 1800s and full of charm and history.

425 Main, Greenport

$750,000

Charming Village Colonial in the Heart of Greenport! Nestled on one of Greenport’s most sought-after streets, this beautifully maintained Colonial blends historic charm with modern comfort. Featuring approximately 1,800 sq ft of living space, this home offers 5 bedrooms, 2 full baths, and inviting living areas filled with natural light. The updated kitchen boasts stainless-steel appliances, stone countertops, and custom cabinetry perfect for entertaining or everyday living. Enjoy a seamless flow from the dining area to the cozy living room, complete with original details and hardwood floors throughout. The home also includes a full basement, private driveway, and a detached garage for added convenience. Outside, the landscaped yard and patio provide the ideal setting for summer gatherings, gardening, or quiet relaxation. Located just moments from Greenport Village shops, award-winning restaurants, beaches, and the LIRR, this property offers the perfect North Fork lifestyle. Whether as a year-round residence or a weekend retreat.

5 Beds ⋅ 3 Baths ⋅ 931803 MLS

Charming Village Colonial in the Heart of Greenport! Nestled on one of Greenport’s most sought-after streets, this beautifully maintained Colonial blends historic charm with modern comfort. Featuring approximately 1,800 sq ft of living space, this home offers 5 bedrooms, 2 full baths, and inviting living areas filled with natural light. The updated kitchen boasts stainless-steel appliances, stone countertops, and custom cabinetry perfect for entertaining or everyday living. Enjoy a seamless flow from the dining area to the cozy living room, complete with original details and hardwood floors throughout. The home also includes a full basement, private driveway, and a detached garage for added convenience. Outside, the landscaped yard and patio provide the ideal setting for summer gatherings, gardening, or quiet relaxation. Located just moments from Greenport Village shops, award-winning restaurants, beaches, and the LIRR, this property offers the perfect North Fork lifestyle. Whether as a year-round residence or a weekend retreat.

35 Washington Avenue, Greenport

$739,000

Greenport Village Farmhouse Built in 2001, Featuring a New Roof (2020), a Welcoming Front Porch, and a Spacious Yard. This Three-Bedroom Home with One and Half Baths, Offers a Good-Sized Living Room and One Especially Large Bedroom with Double Closet Space. Located within One Block from a Park with Playground and a Park with Basketball Courts. A Waterfront Park and Beach is Just Eight Blocks Away and NYC Transportation is Approximately Five Blocks Away. Enjoy Easy Access to Village Shops, Restaurants, Mitchell Park Carousel, Mitchell Park Marina and So Much More from Your Comfortable Home.

3 Beds ⋅ 2 Baths ⋅ 983659 MLS

Greenport Village Farmhouse Built in 2001, Featuring a New Roof (2020), a Welcoming Front Porch, and a Spacious Yard. This Three-Bedroom Home with One and Half Baths, Offers a Good-Sized Living Room and One Especially Large Bedroom with Double Closet Space. Located within One Block from a Park with Playground and a Park with Basketball Courts. A Waterfront Park and Beach is Just Eight Blocks Away and NYC Transportation is Approximately Five Blocks Away. Enjoy Easy Access to Village Shops, Restaurants, Mitchell Park Carousel, Mitchell Park Marina and So Much More from Your Comfortable Home.

416 3rd Street, Greenport

$654,000

Condo in Cliffside Sound Front Complex Featuring Sound Beach, Heated Gunite Pool & Beautiful Sound Views. Easy Access to the Pool and Wow Those Spectacular Sunsets. Complex is closed Jan 15-Mar 15. Cliffside is a full resort facility.

2 Beds ⋅ 2 Baths ⋅ 996367 MLS

Condo in Cliffside Sound Front Complex Featuring Sound Beach, Heated Gunite Pool & Beautiful Sound Views. Easy Access to the Pool and Wow Those Spectacular Sunsets. Complex is closed Jan 15-Mar 15. Cliffside is a full resort facility.

61475 Route 48 Unit #A105, Greenport