Wealthwiserealty.com Search Results

Introducing a stunning waterfront estate on the Long Island Sound, now available for the first time from its original owners. This coastal gem, located in the North Fork, is situated in one of the most sought-after and picturesque areas on the East End. Nestled on nearly 2 acres, this 4,500 sq. ft. residence offers exceptional views and over 200 feet of private waterfront. The spacious open floor plan includes a junior primary ensuite on the first floor, featuring a separate entrance, a wrap-around covered porch, and direct access to the backyard. The gourmet kitchen is designed to capture breathtaking coastal views, boasting custom cabinetry, high-end appliances, beautiful granite countertops, and a spacious island with seating. Al fresco dining is made easy through the breezeway, which leads to the inviting patio and outdoor decks. The living room and dining room, enhanced by a central fireplace, are filled with natural light and feature beautiful wood floors. Tucked behind the fireplace and accessed through sliding barn doors, the home office offers water views and separate access to the yard. Upstairs, the primary bedroom features a balcony and an ensuite bathroom, showcasing stunning views. Additional bedrooms with balconies, a full bathroom, and a bonus space ensure privacy and comfort for guests. An oversized lounge, also with a waterside balcony and fireplace, connects to the kitchen below via a private staircase, creating an ideal space for a quiet retreat. The spacious art studio, built as part of the expansion, has cork flooring and a wall of windows overlooking the outdoor entertaining space, which includes a fully equipped custom kitchen, dining area, stunning pool, and spa amenities. The yard's mature landscaping and expansive lawn create a welcoming atmosphere for gatherings, with curated spaces for relaxation, including Adirondack chairs nestled along the coastline to enjoy the breathtaking sunsets. Additional amenities include an attached garage, greenhouse, a full unfinished basement with side yard access, and a generator. This property is conveniently located near Greenport Village, wineries, farms, and the bucolic landscape that exemplifies the essence of the North Fork region.

4 Beds ⋅ 5 Baths ⋅ 1012436 MLS

Introducing a stunning waterfront estate on the Long Island Sound, now available for the first time from its original owners. This coastal gem, located in the North Fork, is situated in one of the most sought-after and picturesque areas on the East End. Nestled on nearly 2 acres, this 4,500 sq. ft. residence offers exceptional views and over 200 feet of private waterfront. The spacious open floor plan includes a junior primary ensuite on the first floor, featuring a separate entrance, a wrap-around covered porch, and direct access to the backyard. The gourmet kitchen is designed to capture breathtaking coastal views, boasting custom cabinetry, high-end appliances, beautiful granite countertops, and a spacious island with seating. Al fresco dining is made easy through the breezeway, which leads to the inviting patio and outdoor decks. The living room and dining room, enhanced by a central fireplace, are filled with natural light and feature beautiful wood floors. Tucked behind the fireplace and accessed through sliding barn doors, the home office offers water views and separate access to the yard. Upstairs, the primary bedroom features a balcony and an ensuite bathroom, showcasing stunning views. Additional bedrooms with balconies, a full bathroom, and a bonus space ensure privacy and comfort for guests. An oversized lounge, also with a waterside balcony and fireplace, connects to the kitchen below via a private staircase, creating an ideal space for a quiet retreat. The spacious art studio, built as part of the expansion, has cork flooring and a wall of windows overlooking the outdoor entertaining space, which includes a fully equipped custom kitchen, dining area, stunning pool, and spa amenities. The yard's mature landscaping and expansive lawn create a welcoming atmosphere for gatherings, with curated spaces for relaxation, including Adirondack chairs nestled along the coastline to enjoy the breathtaking sunsets. Additional amenities include an attached garage, greenhouse, a full unfinished basement with side yard access, and a generator. This property is conveniently located near Greenport Village, wineries, farms, and the bucolic landscape that exemplifies the essence of the North Fork region.

160 Sound Drive, Greenport

$5,350,000

Perfectly positioned on a bluff overlooking the Long Island Sound, this Nantucket-style cedar-shingled home captures sweeping water views and spectacular sunsets from nearly every vantage point. Multiple waterside decks and balconies make the most of the setting, while a heated pool, outdoor kitchen, and stairs to a private beach create an exceptional environment for summer living and entertaining. Inside, beautifully appointed living spaces include en-suite bedrooms on both the first and second floors, offering flexibility for owners and guests alike. A separate waterside office with balcony round out the second floor. A finished lower level with a private theater provides additional space for recreation. Less than a mile from the heart of Greenport Village, this exceptional waterfront property combines coastal beauty, privacy, and proximity to one of the North Fork’s most desirable destinations.

5 Beds ⋅ 5 Baths ⋅ 1059750 MLS

Perfectly positioned on a bluff overlooking the Long Island Sound, this Nantucket-style cedar-shingled home captures sweeping water views and spectacular sunsets from nearly every vantage point. Multiple waterside decks and balconies make the most of the setting, while a heated pool, outdoor kitchen, and stairs to a private beach create an exceptional environment for summer living and entertaining. Inside, beautifully appointed living spaces include en-suite bedrooms on both the first and second floors, offering flexibility for owners and guests alike. A separate waterside office with balcony round out the second floor. A finished lower level with a private theater provides additional space for recreation. Less than a mile from the heart of Greenport Village, this exceptional waterfront property combines coastal beauty, privacy, and proximity to one of the North Fork’s most desirable destinations.

1000 Sound Drive, Greenport

$4,250,000

Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside gunite pool and an open-concept interior with modern finishes, designed for effortless indoor-outdoor living and year-round enjoyment. Expansive windows fill the home with natural light while capturing stunning sunsets over the water. Included in the offering is an additional .80-acre unimproved soundfront parcel, providing exceptional flexibility—whether to create a multi-generational compound, expand the existing footprint, or develop a second residence for investment or resale. Ideally located in Greenport near beaches, shops, and acclaimed dining, this rare dual-parcel property delivers a compelling blend of coastal lifestyle, privacy, and long-term value.

3 Beds ⋅ 2 Baths ⋅ 923793 MLS

Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside gunite pool and an open-concept interior with modern finishes, designed for effortless indoor-outdoor living and year-round enjoyment. Expansive windows fill the home with natural light while capturing stunning sunsets over the water. Included in the offering is an additional .80-acre unimproved soundfront parcel, providing exceptional flexibility—whether to create a multi-generational compound, expand the existing footprint, or develop a second residence for investment or resale. Ideally located in Greenport near beaches, shops, and acclaimed dining, this rare dual-parcel property delivers a compelling blend of coastal lifestyle, privacy, and long-term value.

56875 Route 48, Greenport

$2,950,000

Greenport's premier Front Street address. High-visibility mixed-use building featuring in-place income and 2,912 square feet available for immediate use. Positioned on the village's busiest corridor with constant foot traffic from tourists, boaters, and ferry passengers. Existing cash flow with clear upside in the North Fork's most sought-after retail location.

989877 MLS

Greenport's premier Front Street address. High-visibility mixed-use building featuring in-place income and 2,912 square feet available for immediate use. Positioned on the village's busiest corridor with constant foot traffic from tourists, boaters, and ferry passengers. Existing cash flow with clear upside in the North Fork's most sought-after retail location.

38-44 Front Street, Greenport

$2,795,000

Home Complete! Exceptional New Construction by well-known local builder set on .42 acres with approximately 4,600 sq. ft., offering 7 bedrooms and 6.5 baths. Sophisticated design features include 10’ ceilings, 4” white oak floors, European windows, Cortizo doors, architectural roof, and Hardie Plank siding. Designer kitchen with Tajah quartz countertops, waterfall island, custom cabinetry, butler’s pantry, Thermador appliances, XO hood and wine refrigerator. Luxurious first-floor junior en suite and stunning second-floor primary suite with spa-like wet room, soaking tub, walk-in closet and mahogany balcony. Finished lower level, gas fireplace, heated 18’ x 36’ in-ground pool, irrigation and professional landscaping. Detached two-car garage with overhead storage. A new construction offering space, style and sought after amenities. Close to 67 Steps Beach and moments from all that Greenport has to offer.

7 Beds ⋅ 7 Baths ⋅ 1053367 MLS

Home Complete! Exceptional New Construction by well-known local builder set on .42 acres with approximately 4,600 sq. ft., offering 7 bedrooms and 6.5 baths. Sophisticated design features include 10’ ceilings, 4” white oak floors, European windows, Cortizo doors, architectural roof, and Hardie Plank siding. Designer kitchen with Tajah quartz countertops, waterfall island, custom cabinetry, butler’s pantry, Thermador appliances, XO hood and wine refrigerator. Luxurious first-floor junior en suite and stunning second-floor primary suite with spa-like wet room, soaking tub, walk-in closet and mahogany balcony. Finished lower level, gas fireplace, heated 18’ x 36’ in-ground pool, irrigation and professional landscaping. Detached two-car garage with overhead storage. A new construction offering space, style and sought after amenities. Close to 67 Steps Beach and moments from all that Greenport has to offer.

1050 Tasker Lane, Greenport

$2,700,000

A Rare Opportunity!!! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long Island. The home itself offers a sun-filled living room with a fireplace and dining area, both featuring floor to ceiling windows which show off the magnificent seascape. The home also hosts an eat-in-kitchen, 3 bedrooms, 3 baths, a large basement, an oversized 2 car garage, and a large deck to enjoy the breathtaking scenery. If being on the water is for you, you've arrived. Don't miss this one time opportunity.

3 Beds ⋅ 3 Baths ⋅ 995366 MLS

A Rare Opportunity!!! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long Island. The home itself offers a sun-filled living room with a fireplace and dining area, both featuring floor to ceiling windows which show off the magnificent seascape. The home also hosts an eat-in-kitchen, 3 bedrooms, 3 baths, a large basement, an oversized 2 car garage, and a large deck to enjoy the breathtaking scenery. If being on the water is for you, you've arrived. Don't miss this one time opportunity.

100 Sound Drive, Greenport

$2,650,000

Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor living, ideal for both relaxed summer getaways and comfortable year-round living. Large windows flood the home with natural light while framing the stunning water views throughout. Ideally located in Greenport, just moments from pristine beaches, charming shops, and renowned restaurants, this meticulously maintained property delivers a seamless blend of privacy, convenience, and coastal elegance.

3 Beds ⋅ 2 Baths ⋅ 975674 MLS

Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor living, ideal for both relaxed summer getaways and comfortable year-round living. Large windows flood the home with natural light while framing the stunning water views throughout. Ideally located in Greenport, just moments from pristine beaches, charming shops, and renowned restaurants, this meticulously maintained property delivers a seamless blend of privacy, convenience, and coastal elegance.

56765 Route 48, Greenport

$2,400,000

Modern Log Home Retreat with Deeded Water Access & ADU Potential | Greenport, NY Discover a truly distinctive single-family modern log home set within one of Greenport’s most coveted peninsula locations. Built in 2003 and thoughtfully renovated in 2021, this 2,396 sq. ft. residence offers 4 bedrooms, 2 baths, and 9 well-proportioned rooms designed for comfort, privacy, and effortless indoor outdoor living. Soaring, classic log home ceilings anchor the interiors, creating a dramatic yet warm atmosphere throughout. The main living spaces flow seamlessly to a sprawling, fully furnished deck—ideal for entertaining or unwinding in complete tranquility. A newly installed saltwater, heated in-ground pool (2025) and a 7-person hot tub elevate the property into a private resort-like setting. Stainless steel appliances, added during the 2021 renovation, have seen minimal use and remain in excellent condition. All Certificates of Occupancy for interior and exterior work have been recently updated (2024/25). Set on 3.88 serene acres and partially surrounded by over 30+acres of protected land and nature preserve, the property offers a rare sense of seclusion while remaining close to the best of the North Fork lifestyle. Enjoy a woodland retreat atmosphere paired with direct water access—including a deeded right of-way and dock rights to a shared deep-water floating dock just across the street on highly desirable Gull Pond. The dock can accommodate vessels approximately 30+ feet, offering the pleasure of dock access without the concerns of flood risk or the need for FEMA flood insurance for the main property. Adding exceptional flexibility, the property includes a 1,000 sq. ft. accessory building, ready for potential ADU transformation (subject to appropriate approvals), creating an opportunity for a true private compound, guest quarters, or additional living space. The location is equally compelling: walk to local favorites such as Portabello of Sterling Harbor, Billy’s on the Bay tiki-style eatery, Islands End Public Golf Course, and Sterling Harbor marinas. A quick bike ride brings you to the maritime village of Greenport, tranquil beaches, and all the charm the area is known for. Documented seasonal rental potential further enhances the property’s appeal. Property Highlights * 4 Bedrooms | 2 Baths | 2,396 Sq. Ft. * 3.88 Acres * Built 2003 | Renovated 2021 * Modern log home with tall, classic ceilings * New heated saltwater pool (2025) + 7-person hot tub * 1,000 sq. ft. accessory building with ADU potential * Deeded water access & dock rights with boat slip * No FEMA flood insurance required * Sold with all contents, if desired * Tax Map: 1000-035-00-03-00-012-001 This is a rare opportunity to own a private North Fork retreat that balances nature, water access, and proximity to Greenport’s vibrant lifestyle. Property can be sold with all contents ready for use if needed.

4 Beds ⋅ 2 Baths ⋅ 945943 MLS

Modern Log Home Retreat with Deeded Water Access & ADU Potential | Greenport, NY Discover a truly distinctive single-family modern log home set within one of Greenport’s most coveted peninsula locations. Built in 2003 and thoughtfully renovated in 2021, this 2,396 sq. ft. residence offers 4 bedrooms, 2 baths, and 9 well-proportioned rooms designed for comfort, privacy, and effortless indoor outdoor living. Soaring, classic log home ceilings anchor the interiors, creating a dramatic yet warm atmosphere throughout. The main living spaces flow seamlessly to a sprawling, fully furnished deck—ideal for entertaining or unwinding in complete tranquility. A newly installed saltwater, heated in-ground pool (2025) and a 7-person hot tub elevate the property into a private resort-like setting. Stainless steel appliances, added during the 2021 renovation, have seen minimal use and remain in excellent condition. All Certificates of Occupancy for interior and exterior work have been recently updated (2024/25). Set on 3.88 serene acres and partially surrounded by over 30+acres of protected land and nature preserve, the property offers a rare sense of seclusion while remaining close to the best of the North Fork lifestyle. Enjoy a woodland retreat atmosphere paired with direct water access—including a deeded right of-way and dock rights to a shared deep-water floating dock just across the street on highly desirable Gull Pond. The dock can accommodate vessels approximately 30+ feet, offering the pleasure of dock access without the concerns of flood risk or the need for FEMA flood insurance for the main property. Adding exceptional flexibility, the property includes a 1,000 sq. ft. accessory building, ready for potential ADU transformation (subject to appropriate approvals), creating an opportunity for a true private compound, guest quarters, or additional living space. The location is equally compelling: walk to local favorites such as Portabello of Sterling Harbor, Billy’s on the Bay tiki-style eatery, Islands End Public Golf Course, and Sterling Harbor marinas. A quick bike ride brings you to the maritime village of Greenport, tranquil beaches, and all the charm the area is known for. Documented seasonal rental potential further enhances the property’s appeal. Property Highlights * 4 Bedrooms | 2 Baths | 2,396 Sq. Ft. * 3.88 Acres * Built 2003 | Renovated 2021 * Modern log home with tall, classic ceilings * New heated saltwater pool (2025) + 7-person hot tub * 1,000 sq. ft. accessory building with ADU potential * Deeded water access & dock rights with boat slip * No FEMA flood insurance required * Sold with all contents, if desired * Tax Map: 1000-035-00-03-00-012-001 This is a rare opportunity to own a private North Fork retreat that balances nature, water access, and proximity to Greenport’s vibrant lifestyle. Property can be sold with all contents ready for use if needed.

1710 Gull Pond Lane, Greenport

$2,399,000

Welcome to your luxury retreat on the North Fork, ideally located in the hamlet of Greenport. This brand new residence offers the perfect blend of sophisticated design, modern comfort and effortless indoor-outdoor living - all just moments from the Long Island Sound with deeded beach rights to a private community beach. Your days can begin with morning walks along the shoreline and end with memorable sunsets. This 2,250 square foot home features an airy open concept floor plan anchored by a gourmet chef’s kitchen with premium finishes and generous entertaining space. The first floor includes a beautifully appointed junior suite, ideal for guests or multigenerational living. Upstairs, the primary suite offers a spa inspired bath, accompanied by two additional bedrooms and a full bathroom. Designed for effortless indoor outdoor living, the backyard is an entertainer’s dream with a spacious patio and a heated saltwater pool. A rear basement entrance adds convenience and flexibility for storage, recreation, or future expansion. Experience refined coastal living in one of Greenport’s most desirable locations—where luxury, comfort, and the Sound’s natural beauty come together. Currently under construction with completed in Fall 2026

4 Beds ⋅ 4 Baths ⋅ 1000563 MLS

Welcome to your luxury retreat on the North Fork, ideally located in the hamlet of Greenport. This brand new residence offers the perfect blend of sophisticated design, modern comfort and effortless indoor-outdoor living - all just moments from the Long Island Sound with deeded beach rights to a private community beach. Your days can begin with morning walks along the shoreline and end with memorable sunsets. This 2,250 square foot home features an airy open concept floor plan anchored by a gourmet chef’s kitchen with premium finishes and generous entertaining space. The first floor includes a beautifully appointed junior suite, ideal for guests or multigenerational living. Upstairs, the primary suite offers a spa inspired bath, accompanied by two additional bedrooms and a full bathroom. Designed for effortless indoor outdoor living, the backyard is an entertainer’s dream with a spacious patio and a heated saltwater pool. A rear basement entrance adds convenience and flexibility for storage, recreation, or future expansion. Experience refined coastal living in one of Greenport’s most desirable locations—where luxury, comfort, and the Sound’s natural beauty come together. Currently under construction with completed in Fall 2026

1760 McCann Lane, Greenport

$2,100,000

This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

5 Beds ⋅ 5 Baths ⋅ L3579812 MLS

This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

151 Bay Avenue, Greenport

$1,975,000

One of Greenport’s most iconic homes, the William Corey House was built circa 1882 and stands as a beautiful testament to the village’s rich maritime history. Built for William D. Corey of Webb & Corey, a prominent ship chandlery that supplied vessels passing through Greenport’s bustling harbor, this distinguished residence has a direct connection to the working waterfront that helped shape the village. Set on a generous double lot graced by magnificent mature beech trees and a charming carriage house, the residence is distinguished by its slate roof, scalloped shingles, and decorative brackets. A gracious wraparound porch framed by Ionic columns welcomes visitors, while a Colonial-style doorway with an arched transom and sidelights adds to its timeless appeal. Together, these beautifully preserved period details reflect the craftsmanship and prosperity of Greenport’s years as a thriving port. Long admired by residents and visitors alike, 440 1st Street represents a rare opportunity to own a meaningful piece of Greenport’s architectural and maritime heritage. Awaiting its next steward, this extraordinary property offers the chance to restore its beauty, honor its history, and write the next chapter of one of the village’s most recognizable homes.

5 Beds ⋅ 2 Baths ⋅ 1056150 MLS

One of Greenport’s most iconic homes, the William Corey House was built circa 1882 and stands as a beautiful testament to the village’s rich maritime history. Built for William D. Corey of Webb & Corey, a prominent ship chandlery that supplied vessels passing through Greenport’s bustling harbor, this distinguished residence has a direct connection to the working waterfront that helped shape the village. Set on a generous double lot graced by magnificent mature beech trees and a charming carriage house, the residence is distinguished by its slate roof, scalloped shingles, and decorative brackets. A gracious wraparound porch framed by Ionic columns welcomes visitors, while a Colonial-style doorway with an arched transom and sidelights adds to its timeless appeal. Together, these beautifully preserved period details reflect the craftsmanship and prosperity of Greenport’s years as a thriving port. Long admired by residents and visitors alike, 440 1st Street represents a rare opportunity to own a meaningful piece of Greenport’s architectural and maritime heritage. Awaiting its next steward, this extraordinary property offers the chance to restore its beauty, honor its history, and write the next chapter of one of the village’s most recognizable homes.

440 1st Street, Greenport

$1,950,000

Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable accommodations, while a full unfinished basement presents excellent potential for additional living space, whether for a media room, gym, recreation area, or some combination. The primary bedroom enjoys vaulted ceilings, plenty of natural light and a generous ensuite bath. Outside, a heated saltwater pool is set within mature, thoughtfully designed landscaping that provides both privacy and a beautifully established backdrop for summer days. Deeded HOA access to a pristine Sound beach, Eastern Shores, completes this exceptional offering. Located less than a mile from the heart of Greenport Village, home to coveted restaurants, boutique shops, coffee shops, and marinas.

4 Beds ⋅ 3 Baths ⋅ 970247 MLS

Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable accommodations, while a full unfinished basement presents excellent potential for additional living space, whether for a media room, gym, recreation area, or some combination. The primary bedroom enjoys vaulted ceilings, plenty of natural light and a generous ensuite bath. Outside, a heated saltwater pool is set within mature, thoughtfully designed landscaping that provides both privacy and a beautifully established backdrop for summer days. Deeded HOA access to a pristine Sound beach, Eastern Shores, completes this exceptional offering. Located less than a mile from the heart of Greenport Village, home to coveted restaurants, boutique shops, coffee shops, and marinas.

660 Sutton Place, Greenport

$1,800,000

2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!

1008060 MLS

2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!

69430 Main Road, Greenport

$1,799,000

Greenport Gem — Timeless Elegance & Coastal Living Tucked privately behind tall hedges on a beautifully landscaped, gated corner property, this stately 1930s American Square offers an exceptional blend of historic character, refined comfort, and the coveted Greenport lifestyle. Meticulously restored in 2012 and gently lived in since, the home retains its original woodwork, doors, and flooring, preserving the craftsmanship and character of a bygone era while offering modern comforts, including central air conditioning. A spacious kitchen flows effortlessly into the inviting living areas, creating a warm and sophisticated setting for entertaining and relaxed everyday living. Outside, the lush grounds create a private oasis with mature landscaping, generous outdoor space, and ample room for a pool. A detached 440-square-foot garage offers additional flexibility and convenience. Just moments from Greenport’s sandy 4th, 5th, and 6th Street bay beaches and parks, and close to the Village’s celebrated shops, restaurants, marinas, and NYC transportation, this distinctive property presents a rare opportunity to enjoy timeless architecture, exceptional privacy, and effortless coastal living in one of the North Fork’s most desirable destinations. See Photos or Attachment for Floor Plan and Survey.

4 Beds ⋅ 3 Baths ⋅ 942025 MLS

Greenport Gem — Timeless Elegance & Coastal Living Tucked privately behind tall hedges on a beautifully landscaped, gated corner property, this stately 1930s American Square offers an exceptional blend of historic character, refined comfort, and the coveted Greenport lifestyle. Meticulously restored in 2012 and gently lived in since, the home retains its original woodwork, doors, and flooring, preserving the craftsmanship and character of a bygone era while offering modern comforts, including central air conditioning. A spacious kitchen flows effortlessly into the inviting living areas, creating a warm and sophisticated setting for entertaining and relaxed everyday living. Outside, the lush grounds create a private oasis with mature landscaping, generous outdoor space, and ample room for a pool. A detached 440-square-foot garage offers additional flexibility and convenience. Just moments from Greenport’s sandy 4th, 5th, and 6th Street bay beaches and parks, and close to the Village’s celebrated shops, restaurants, marinas, and NYC transportation, this distinctive property presents a rare opportunity to enjoy timeless architecture, exceptional privacy, and effortless coastal living in one of the North Fork’s most desirable destinations. See Photos or Attachment for Floor Plan and Survey.

1025 9th Street, Greenport

$1,595,000

A rare and exceptional offering in the heart of Greenport—one of the only duplex-style properties of its kind on the North Fork—this fully turnkey property delivers a unique combination of lifestyle, flexibility, and proven income potential. Located within Greenport Village and offering approximately 3,376 square feet of living space, this back-to-back duplex features two fully independent, two-story residences, each with its own full basement, central air conditioning, and private living areas as well as two electric panels, two meters, two propane tanks and separate basements. Built approximately 7 years ago, the property offers the advantages of newer construction, including modern systems, efficient design, and low-maintenance living. The front residence offers 4 bedrooms and 2.5 baths, highlighted by a welcoming covered front porch, fireplace, and a full basement with 8-foot ceilings—ideal for expansion, recreation, or storage. The rear residence features 3 bedrooms and 2.5 baths, a gas fireplace, and a full walk-out basement, providing excellent privacy and functionality. Outdoor features include a spacious back deck, side yard with a fire pit and a large yard, offering ample room for entertaining or relaxation. Being sold fully furnished and turnkey, the property is ready for immediate use. With a proven history of generating approximately $125,000 annually, this property presents a compelling opportunity for both end-users and investors. Ideally situated within walking distance to the vibrant village center, the Greenport Free Library, and public transportation, the property provides easy access to waterfront dining, marinas, shops, and all that the North Fork has to offer. This is more than a home—it’s a rare opportunity to own a flexible, income-producing property in one of the North Fork’s most sought-after locations.

7 Beds ⋅ 6 Baths ⋅ 982976 MLS

A rare and exceptional offering in the heart of Greenport—one of the only duplex-style properties of its kind on the North Fork—this fully turnkey property delivers a unique combination of lifestyle, flexibility, and proven income potential. Located within Greenport Village and offering approximately 3,376 square feet of living space, this back-to-back duplex features two fully independent, two-story residences, each with its own full basement, central air conditioning, and private living areas as well as two electric panels, two meters, two propane tanks and separate basements. Built approximately 7 years ago, the property offers the advantages of newer construction, including modern systems, efficient design, and low-maintenance living. The front residence offers 4 bedrooms and 2.5 baths, highlighted by a welcoming covered front porch, fireplace, and a full basement with 8-foot ceilings—ideal for expansion, recreation, or storage. The rear residence features 3 bedrooms and 2.5 baths, a gas fireplace, and a full walk-out basement, providing excellent privacy and functionality. Outdoor features include a spacious back deck, side yard with a fire pit and a large yard, offering ample room for entertaining or relaxation. Being sold fully furnished and turnkey, the property is ready for immediate use. With a proven history of generating approximately $125,000 annually, this property presents a compelling opportunity for both end-users and investors. Ideally situated within walking distance to the vibrant village center, the Greenport Free Library, and public transportation, the property provides easy access to waterfront dining, marinas, shops, and all that the North Fork has to offer. This is more than a home—it’s a rare opportunity to own a flexible, income-producing property in one of the North Fork’s most sought-after locations.

213-215 North Street, Greenport

$1,499,000

Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering true farmstead character. A large, established two thirds of an acre vegetable garden and an active farm stand highlight the property’s agricultural potential, while the watering hole rises and falls with the rains. This less than one-mile pastoral Greenport lane has over 130 acres of preserve land with another 50 plus acres of land on this lane soon to be preserved. Whether you choose to reimagine, repurpose, or simply enjoy this unique homestead as it is, the possibilities are abundant. A memorable bay beach just under one mile away. Please do not walk the grounds unattended.

4 Beds ⋅ 2 Baths ⋅ 934356 MLS

Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering true farmstead character. A large, established two thirds of an acre vegetable garden and an active farm stand highlight the property’s agricultural potential, while the watering hole rises and falls with the rains. This less than one-mile pastoral Greenport lane has over 130 acres of preserve land with another 50 plus acres of land on this lane soon to be preserved. Whether you choose to reimagine, repurpose, or simply enjoy this unique homestead as it is, the possibilities are abundant. A memorable bay beach just under one mile away. Please do not walk the grounds unattended.

1760 Albertson Lane, Greenport

$1,495,000

Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 850 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 870 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and separated living room, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly installed crushed-stone driveway with Belgian block edging, a large rear lawn, full irrigation, and a charming front porch. A substantial 450-square-foot, two-car garage and additional storage shed further enhance the property's functionality. Whether you're an investor seeking a ready-made income-producing property or an end user looking to offset carrying costs with rental income, 430 First Street presents a compelling opportunity in the heart of Greenport Village. Located just two blocks from Greenport's vibrant business district, the property offers convenient access to public transportation, shops, restaurants, grocery stores, local farm stands, parks, and beaches—all while providing the space, condition, and versatility that make this a truly special offering.

6 Beds ⋅ 2 Baths ⋅ 1043177 MLS

Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 850 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 870 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and separated living room, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly installed crushed-stone driveway with Belgian block edging, a large rear lawn, full irrigation, and a charming front porch. A substantial 450-square-foot, two-car garage and additional storage shed further enhance the property's functionality. Whether you're an investor seeking a ready-made income-producing property or an end user looking to offset carrying costs with rental income, 430 First Street presents a compelling opportunity in the heart of Greenport Village. Located just two blocks from Greenport's vibrant business district, the property offers convenient access to public transportation, shops, restaurants, grocery stores, local farm stands, parks, and beaches—all while providing the space, condition, and versatility that make this a truly special offering.

430 1st Street, Greenport

$1,310,000

This classic Greenport Village Craftsman has the kind of charm that is getting harder to find — bright, airy rooms, beautiful period detail, and an easy coastal feel just one block from the beach. Front and back porches provide multiple outdoor seating areas. Inside, the home features coffered ceilings, warm wood floors, and sun-filled living and dining spaces. Outside, the private, fully fenced backyard is well suited for summer living, w/wisteria-covered arbor for dining & entertaining. room for a pool. the detached garage with outdoor shower could work well as a pool house, studio, or additional entertaining space. This special property is close to a sandy Bay beach, the LIRR, SI Ferry, restaurants and the lively Village downtown. Perfectly located to explore the vineyards, farm stands, fishing spots and all that the North Fork offers.

3 Beds ⋅ 2 Baths ⋅ 966420 MLS

This classic Greenport Village Craftsman has the kind of charm that is getting harder to find — bright, airy rooms, beautiful period detail, and an easy coastal feel just one block from the beach. Front and back porches provide multiple outdoor seating areas. Inside, the home features coffered ceilings, warm wood floors, and sun-filled living and dining spaces. Outside, the private, fully fenced backyard is well suited for summer living, w/wisteria-covered arbor for dining & entertaining. room for a pool. the detached garage with outdoor shower could work well as a pool house, studio, or additional entertaining space. This special property is close to a sandy Bay beach, the LIRR, SI Ferry, restaurants and the lively Village downtown. Perfectly located to explore the vineyards, farm stands, fishing spots and all that the North Fork offers.

210 5th Street, Greenport

$1,300,000

Welcome to 402 5th Street, a 4 bedroom, 2 full bathroom historic Victorian located in the heart of west Dublin on a double lot, with plenty of room for an in-ground pool and just 3 blocks to a sandy bay beach. The home is also zoned to be converted to a 2-family dwelling. The residence offers original wide plank flooring, a large back deck and private back yard with a large shed. On the first floor, a side entrance leads to a formal kitchen, dining room, den or reading area and living room with a colossal fireplace. The second floor primary bedroom has a cathedral ceiling with skylights and plentiful amounts of natural light. There are three additional bedrooms, a full bathroom and separate exterior staircase leading to the second floor. The home is located a few blocks from the heart of Greenport Village.

4 Beds ⋅ 2 Baths ⋅ 1058255 MLS

Welcome to 402 5th Street, a 4 bedroom, 2 full bathroom historic Victorian located in the heart of west Dublin on a double lot, with plenty of room for an in-ground pool and just 3 blocks to a sandy bay beach. The home is also zoned to be converted to a 2-family dwelling. The residence offers original wide plank flooring, a large back deck and private back yard with a large shed. On the first floor, a side entrance leads to a formal kitchen, dining room, den or reading area and living room with a colossal fireplace. The second floor primary bedroom has a cathedral ceiling with skylights and plentiful amounts of natural light. There are three additional bedrooms, a full bathroom and separate exterior staircase leading to the second floor. The home is located a few blocks from the heart of Greenport Village.

402 5th Street, Greenport

$1,297,000

Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this versatile property features a porch, deck, patio, and 1-car garage, along with additional outdoor amenities including a cabana and hot tub, all conveniently located near local restaurants, shopping, and transportation.

4 Beds ⋅ 2 Baths ⋅ 980655 MLS

Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this versatile property features a porch, deck, patio, and 1-car garage, along with additional outdoor amenities including a cabana and hot tub, all conveniently located near local restaurants, shopping, and transportation.

407 Wiggins Street, Greenport

$1,297,000

Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this flexible property offers central air conditioning, front porch, deck, and patio, all conveniently close to local restaurants, shopping, and transportation. Turnkey appeal and income-producing potential enhance this compelling offering.

4 Beds ⋅ 2 Baths ⋅ 980657 MLS

Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this flexible property offers central air conditioning, front porch, deck, and patio, all conveniently close to local restaurants, shopping, and transportation. Turnkey appeal and income-producing potential enhance this compelling offering.

401 Wiggins Street, Greenport

$1,276,000

Welcome to 550 Madison Avenue in Greenport, a thoughtfully designed New Construction farmhouse that feels comfortable from the moment you arrive. The covered front porch is more than an architectural detail. There is actually room for a chair and side table, creating the perfect spot for a quiet morning coffee. Inside, wide 6-inch oak floors connect the bright, open living spaces. The powder room is conveniently located near the front entrance, but it is tucked far enough away from the open living room, dining area, and kitchen to give everyone a little privacy when the house is full. The custom kitchen design brings together the features buyers keep asking for, including a paneled refrigerator, a full pantry closet, open shelving, generous cabinetry, and a kitchen sink positioned beneath a window overlooking the backyard. Even doing the dishes comes with a view of the established maple trees. A full glass slider in the dining area fills the back of the home with natural light and creates an easy connection to the outdoor entertaining spaces and grill. The backyard views can also be enjoyed from the living room, making the surrounding landscape feel like part of the interior design. Upstairs, the primary bedroom features a peaceful en-suite bathroom with distinctive tile flooring and calm, carefully selected finishes. Even the first-floor powder room has beautiful wallpaper, adding personality and making this New Construction home feel intentional rather than predictable. The fully fenced backyard is surrounded by established maple trees, creating a quiet and private setting that feels like a hidden corner of Greenport. The newly installed stone patio includes an outdoor cushioned conversation area, a separate outdoor dining patio, and a dedicated fire pit for evenings under the trees. There is also room to explore the possibility of adding a pool without making the yard feel crowded. The location brings the North Fork lifestyle within easy reach. The Greenport LIRR station and Hampton Jitney stop are approximately half a mile away for convenient transportation to New York City. Aldo’s Coffee is about a three-minute bike ride or a ten-minute walk, with Greenport Village shops, restaurants, waterfront destinations, and local beaches all close enough to enjoy without always getting back into the car. New Construction, a custom kitchen, paneled appliances, wide oak floors, en-suite bathrooms, a fenced backyard, mature trees, outdoor entertaining spaces, and easy access to Greenport Village. This might be the one you have been waiting for. You really need to come see it. In the evening it sparks with fireflies to capture summer vibes in Greenport Village.

3 Beds ⋅ 3 Baths ⋅ 998976 MLS

Welcome to 550 Madison Avenue in Greenport, a thoughtfully designed New Construction farmhouse that feels comfortable from the moment you arrive. The covered front porch is more than an architectural detail. There is actually room for a chair and side table, creating the perfect spot for a quiet morning coffee. Inside, wide 6-inch oak floors connect the bright, open living spaces. The powder room is conveniently located near the front entrance, but it is tucked far enough away from the open living room, dining area, and kitchen to give everyone a little privacy when the house is full. The custom kitchen design brings together the features buyers keep asking for, including a paneled refrigerator, a full pantry closet, open shelving, generous cabinetry, and a kitchen sink positioned beneath a window overlooking the backyard. Even doing the dishes comes with a view of the established maple trees. A full glass slider in the dining area fills the back of the home with natural light and creates an easy connection to the outdoor entertaining spaces and grill. The backyard views can also be enjoyed from the living room, making the surrounding landscape feel like part of the interior design. Upstairs, the primary bedroom features a peaceful en-suite bathroom with distinctive tile flooring and calm, carefully selected finishes. Even the first-floor powder room has beautiful wallpaper, adding personality and making this New Construction home feel intentional rather than predictable. The fully fenced backyard is surrounded by established maple trees, creating a quiet and private setting that feels like a hidden corner of Greenport. The newly installed stone patio includes an outdoor cushioned conversation area, a separate outdoor dining patio, and a dedicated fire pit for evenings under the trees. There is also room to explore the possibility of adding a pool without making the yard feel crowded. The location brings the North Fork lifestyle within easy reach. The Greenport LIRR station and Hampton Jitney stop are approximately half a mile away for convenient transportation to New York City. Aldo’s Coffee is about a three-minute bike ride or a ten-minute walk, with Greenport Village shops, restaurants, waterfront destinations, and local beaches all close enough to enjoy without always getting back into the car. New Construction, a custom kitchen, paneled appliances, wide oak floors, en-suite bathrooms, a fenced backyard, mature trees, outdoor entertaining spaces, and easy access to Greenport Village. This might be the one you have been waiting for. You really need to come see it. In the evening it sparks with fireflies to capture summer vibes in Greenport Village.

550 Madison Avenue, Greenport

$1,225,000

This highly visible commercial property sits on the Main Road in Greenport, with the benefit of traffic to and from nearby Greenport Village. The spacious +/- 6000 sf building set on .33 acres offers a variety of potential business opportunities - retail, service, restaurant, professional offices. LB zoning.

856731 MLS

This highly visible commercial property sits on the Main Road in Greenport, with the benefit of traffic to and from nearby Greenport Village. The spacious +/- 6000 sf building set on .33 acres offers a variety of potential business opportunities - retail, service, restaurant, professional offices. LB zoning.

69465 Main Road, Greenport

$1,175,000

Pool, private beach access and the North Fork lifestyle—all in one Greenport property. Set on approximately one-third acre, this spacious Cape offers 4 bedrooms, 2 full baths and approximately 2,400 square feet of above-grade living space, surrounded by mature landscaping and exceptional outdoor amenities. The private backyard is designed for summer living and entertaining, centered around an in-ground swimming pool, expansive outdoor areas and a secluded firepit setting. Just beyond home, enjoy private community beach access (Sterling Eastern Shores)—an increasingly rare amenity and the perfect setting for swimming, relaxing by the water and unforgettable Greenport sunsets. Inside, generous living spaces include a fireplace living room, separate den, open kitchen and dining areas, large bedrooms, first-floor laundry and flexible home-office space. The layout provides room to gather as well as plenty of space to spread out. A substantial finished lower level with separate exterior entrance provides additional flexible-use space, including laundry, a renovated bath and additional finished rooms. An oversized workshop adds even more versatility for hobbies, projects and storage. Whether you’re looking for a year-round North Fork home or a weekend retreat, this home offers a combination that’s difficult to duplicate space, privacy, a swimming pool, private beach access and the Greenport lifestyle.

4 Beds ⋅ 3 Baths ⋅ 1037504 MLS

Pool, private beach access and the North Fork lifestyle—all in one Greenport property. Set on approximately one-third acre, this spacious Cape offers 4 bedrooms, 2 full baths and approximately 2,400 square feet of above-grade living space, surrounded by mature landscaping and exceptional outdoor amenities. The private backyard is designed for summer living and entertaining, centered around an in-ground swimming pool, expansive outdoor areas and a secluded firepit setting. Just beyond home, enjoy private community beach access (Sterling Eastern Shores)—an increasingly rare amenity and the perfect setting for swimming, relaxing by the water and unforgettable Greenport sunsets. Inside, generous living spaces include a fireplace living room, separate den, open kitchen and dining areas, large bedrooms, first-floor laundry and flexible home-office space. The layout provides room to gather as well as plenty of space to spread out. A substantial finished lower level with separate exterior entrance provides additional flexible-use space, including laundry, a renovated bath and additional finished rooms. An oversized workshop adds even more versatility for hobbies, projects and storage. Whether you’re looking for a year-round North Fork home or a weekend retreat, this home offers a combination that’s difficult to duplicate space, privacy, a swimming pool, private beach access and the Greenport lifestyle.

130 Tasker Lane, Greenport

$1,149,900

Welcome to this beautifully appointed single-family residence ideally situated just minutes from the charming village of Greenport. Blending modern amenities with classic coastal charm, this property offers not only an exceptional retreat in one of Long Island’s most sought-after locations—but also a compelling opportunity as a fully functional or potential income-producing short-term rental. Whether you’re seeking a weekend escape, a second home that offsets its own costs, or a turnkey investment in the thriving North Fork vacation market, this home delivers versatility and value. INTERIOR FEATURES: The home showcases a thoughtfully designed open-concept layout. The gourmet kitchen features white cabinetry, granite countertops, subway tile backsplash, and premium stainless steel appliances. The spacious living area is anchored by a cozy fireplace, while hardwood floors flow throughout. Multiple bedrooms offer comfort and privacy, complemented by updated bathrooms featuring glass-enclosed showers, stone tile walls, and granite countertops—ideal for both personal use and guest accommodations. OUTDOOR LIVING: Set on over half an acre, the expansive property is designed for relaxation and entertainment. A stunning rectangular swimming pool, stone-paved deck, and extensive patio space create a resort-like atmosphere highly desirable for short-term guests and homeowners alike. Mature landscaping and privacy fencing provide a serene and secluded outdoor setting. ADDITIONAL AMENITIES: Unfinished basement offering excellent potential for recreation space or added value Dedicated laundry room Ceiling fans throughout Attached garage with paved parking INCOME & INVESTMENT POTENTIAL: Located in one of the North Fork’s most in-demand vacation destinations, this property is well-positioned for short-term rental use. With strong seasonal demand driven by wineries, beaches, and year-round tourism, buyers have the opportunity to generate income while enjoying personal use. Ideal for those looking to own a lifestyle property that can also serve as a revenue-generating asset. LOCATION & LIFESTYLE: Just a short drive from historic Greenport Village, this home offers easy access to boutique shopping, acclaimed restaurants, and waterfront activities. Enjoy proximity to award-winning wineries, pristine beaches, marinas, and a vibrant calendar of community events including the Maritime Festival and Winter Wonderland. The North Fork’s renowned farm-to-table dining, farmers markets, art galleries, and cultural venues are all within reach, along with convenient access to the Hampton Jitney and LIRR. This property offers more than just a home—it’s an opportunity to experience the best of the North Fork lifestyle while capitalizing on one of the region’s most desirable and in-demand markets. Whether for personal enjoyment, investment, or both, this is a rare offering in Greenport.

3 Beds ⋅ 2 Baths ⋅ 921412 MLS

Welcome to this beautifully appointed single-family residence ideally situated just minutes from the charming village of Greenport. Blending modern amenities with classic coastal charm, this property offers not only an exceptional retreat in one of Long Island’s most sought-after locations—but also a compelling opportunity as a fully functional or potential income-producing short-term rental. Whether you’re seeking a weekend escape, a second home that offsets its own costs, or a turnkey investment in the thriving North Fork vacation market, this home delivers versatility and value. INTERIOR FEATURES: The home showcases a thoughtfully designed open-concept layout. The gourmet kitchen features white cabinetry, granite countertops, subway tile backsplash, and premium stainless steel appliances. The spacious living area is anchored by a cozy fireplace, while hardwood floors flow throughout. Multiple bedrooms offer comfort and privacy, complemented by updated bathrooms featuring glass-enclosed showers, stone tile walls, and granite countertops—ideal for both personal use and guest accommodations. OUTDOOR LIVING: Set on over half an acre, the expansive property is designed for relaxation and entertainment. A stunning rectangular swimming pool, stone-paved deck, and extensive patio space create a resort-like atmosphere highly desirable for short-term guests and homeowners alike. Mature landscaping and privacy fencing provide a serene and secluded outdoor setting. ADDITIONAL AMENITIES: Unfinished basement offering excellent potential for recreation space or added value Dedicated laundry room Ceiling fans throughout Attached garage with paved parking INCOME & INVESTMENT POTENTIAL: Located in one of the North Fork’s most in-demand vacation destinations, this property is well-positioned for short-term rental use. With strong seasonal demand driven by wineries, beaches, and year-round tourism, buyers have the opportunity to generate income while enjoying personal use. Ideal for those looking to own a lifestyle property that can also serve as a revenue-generating asset. LOCATION & LIFESTYLE: Just a short drive from historic Greenport Village, this home offers easy access to boutique shopping, acclaimed restaurants, and waterfront activities. Enjoy proximity to award-winning wineries, pristine beaches, marinas, and a vibrant calendar of community events including the Maritime Festival and Winter Wonderland. The North Fork’s renowned farm-to-table dining, farmers markets, art galleries, and cultural venues are all within reach, along with convenient access to the Hampton Jitney and LIRR. This property offers more than just a home—it’s an opportunity to experience the best of the North Fork lifestyle while capitalizing on one of the region’s most desirable and in-demand markets. Whether for personal enjoyment, investment, or both, this is a rare offering in Greenport.

380 Homestead Way, Greenport

$1,100,000

What caught my attention at 216 Monsell Place is how much of the original Greenport farmhouse feeling is still here, but the house has evolved into a layout that works really well today. You start with that wide wraparound porch. I can immediately picture sitting out there with coffee in the morning or having a drink at the end of the day. Then you walk inside and the pine floors, wood-burning fireplace and natural character remind you why these older North Fork homes are so appealing in the first place. The kitchen feels fresh and updated with new appliances, but what I really noticed was the light. There is a full-glass door at the side entrance, and in the afternoon the sunlight comes right into the kitchen. It gives the room a completely different feel and connects it visually with the backyard. Upstairs, there are three bedrooms, and one of them has some really interesting ceiling details that you just don't expect until you walk into the room. There are built-in closets, a second full bathroom, and another bright space with a great group of windows that I immediately thought would make an awesome home office. Then you walk outside and realize just how much yard there is. For Greenport Village, this is a really generous lot. You already have established trees and a great storage barn, but there is still plenty of space to have some fun with it. I can picture outdoor dining, gardens, a fire pit, lounge areas or simply a big backyard where everyone can spread out. And I like where it sits in the Village. Grab a bike and you can head over to Klipp's Park Beach, Smugglers Cove or Billy's By The Bay and spend an afternoon around the water and the marinas. For me, that's what makes this house interesting. A lot of the charm is already here, but there are still enough possibilities that you can start imagining what you would do with it.

3 Beds ⋅ 2 Baths ⋅ 1040671 MLS

What caught my attention at 216 Monsell Place is how much of the original Greenport farmhouse feeling is still here, but the house has evolved into a layout that works really well today. You start with that wide wraparound porch. I can immediately picture sitting out there with coffee in the morning or having a drink at the end of the day. Then you walk inside and the pine floors, wood-burning fireplace and natural character remind you why these older North Fork homes are so appealing in the first place. The kitchen feels fresh and updated with new appliances, but what I really noticed was the light. There is a full-glass door at the side entrance, and in the afternoon the sunlight comes right into the kitchen. It gives the room a completely different feel and connects it visually with the backyard. Upstairs, there are three bedrooms, and one of them has some really interesting ceiling details that you just don't expect until you walk into the room. There are built-in closets, a second full bathroom, and another bright space with a great group of windows that I immediately thought would make an awesome home office. Then you walk outside and realize just how much yard there is. For Greenport Village, this is a really generous lot. You already have established trees and a great storage barn, but there is still plenty of space to have some fun with it. I can picture outdoor dining, gardens, a fire pit, lounge areas or simply a big backyard where everyone can spread out. And I like where it sits in the Village. Grab a bike and you can head over to Klipp's Park Beach, Smugglers Cove or Billy's By The Bay and spend an afternoon around the water and the marinas. For me, that's what makes this house interesting. A lot of the charm is already here, but there are still enough possibilities that you can start imagining what you would do with it.

216 Monsell Place, Greenport

$1,100,000

What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the landscape each season. Inside, the home has an easy, open flow with wood floors, a spacious hallway leading to the bedrooms, and a living room and kitchen that connect naturally for everyday living and entertaining. Just off the garage, the laundry room and mudroom create a practical drop zone for shoes, bags, beach gear and everything else that helps keep the main living spaces organized. The fenced backyard has its own personality, with an outdoor fire pit, established vegetable gardens, a huge fig tree and an additional garden shed for tools, bikes and outdoor storage. It is the kind of yard that already feels lived in, cared for and ready to enjoy. Location adds another layer to the lifestyle. Iconic 67 Steps Beach is within walking distance for those incredible sunsets over Long Island Sound, while Greenport's coffee shops, restaurants and village destinations are close enough that grabbing your morning coffee does not always have to involve getting in the car. It is a home that combines comfortable everyday living with gardens, outdoor spaces and one of the things that makes Greenport so special: the ability to enjoy the beach, the village and the North Fork lifestyle right outside your door.

3 Beds ⋅ 2 Baths ⋅ 1040676 MLS

What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the landscape each season. Inside, the home has an easy, open flow with wood floors, a spacious hallway leading to the bedrooms, and a living room and kitchen that connect naturally for everyday living and entertaining. Just off the garage, the laundry room and mudroom create a practical drop zone for shoes, bags, beach gear and everything else that helps keep the main living spaces organized. The fenced backyard has its own personality, with an outdoor fire pit, established vegetable gardens, a huge fig tree and an additional garden shed for tools, bikes and outdoor storage. It is the kind of yard that already feels lived in, cared for and ready to enjoy. Location adds another layer to the lifestyle. Iconic 67 Steps Beach is within walking distance for those incredible sunsets over Long Island Sound, while Greenport's coffee shops, restaurants and village destinations are close enough that grabbing your morning coffee does not always have to involve getting in the car. It is a home that combines comfortable everyday living with gardens, outdoor spaces and one of the things that makes Greenport so special: the ability to enjoy the beach, the village and the North Fork lifestyle right outside your door.

435 Sound Road, Greenport

$999,750

BRING ALL OFFERS GREENPORT, NY — RELAUNCHED UNDER $1 MILLION Limited supply. Strong demand. Location, location, location. Real estate values have always been influenced by location, supply and demand—and Greenport continues to attract buyers looking for the unique lifestyle of the North Fork. Now is the time to take another look at 336 2nd Street, newly offered at $999,750. This totally renovated approximately 1,800 sq. ft. residence offers 4 bedrooms and 2 full baths in a desirable Greenport Village location. Fresh, clean and move-in ready. The property has generated plenty of viewer interest. Now, with its new price under $1 million, it is positioned to sell. If you’ve been looking for a home in Greenport, don’t pass this one by. 336 2nd Street, Greenport, NY 4 Bedrooms | 2 Baths | Approx. 1,800 Sq. Ft. NEW PRICE: $999,750 Location. Opportunity. Greenport. Come take another look.

4 Beds ⋅ 2 Baths ⋅ 940213 MLS

BRING ALL OFFERS GREENPORT, NY — RELAUNCHED UNDER $1 MILLION Limited supply. Strong demand. Location, location, location. Real estate values have always been influenced by location, supply and demand—and Greenport continues to attract buyers looking for the unique lifestyle of the North Fork. Now is the time to take another look at 336 2nd Street, newly offered at $999,750. This totally renovated approximately 1,800 sq. ft. residence offers 4 bedrooms and 2 full baths in a desirable Greenport Village location. Fresh, clean and move-in ready. The property has generated plenty of viewer interest. Now, with its new price under $1 million, it is positioned to sell. If you’ve been looking for a home in Greenport, don’t pass this one by. 336 2nd Street, Greenport, NY 4 Bedrooms | 2 Baths | Approx. 1,800 Sq. Ft. NEW PRICE: $999,750 Location. Opportunity. Greenport. Come take another look.

336 2ND Street, Greenport

$925,000

What surprised me is the option to consider a 2.7% assumable mortgage, a ownership member of the 2.5 acre beach and an updated home with updates and charm. The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling. Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just pours into the room. From there, everything connects. The dining area opens visually to the kitchen, where the sink sits under a window looking out toward the outdoor dining table, and the living room is right there too. You can literally be cooking, sitting at the table or relaxing on the sofa and still see the TV. It’s a really comfortable layout for everyday living. The two bedrooms are nicely separated into the sleeping side of the house with the full bathroom nearby. The larger bedroom easily accommodates a king size bed, and the second works perfectly with a queen, so it feels much more like a year round home than just a little summer cottage. But the backyard might be where I would spend most of my time. A deck runs along the length of the house with room for outdoor dining and seating, then there’s another spot with double lounge chairs where you could disappear with a book or just sit there and do absolutely nothing, which honestly sounds pretty good. At night, string lights run through the trees and completely change the atmosphere around the fire pit, with seating for six or more. Between the established plantings, mature trees and detached two-car garage, the backyard feels private, comfortable and finished. Then you discover Conkling Point Beach. The association provides access to this beautiful 2.5 acre crescent shaped sandbar just a few doors away. It has sandy beach, open water views toward The Pridwin and Sunset Beach on Shelter Island, and some incredible spots to settle in with your beach chairs beneath the windswept trees. With the breeze coming off the water and the sun dropping across the horizon, it can honestly feel like you found your own little island. What makes the location work so well is that you get that quiet beach community atmosphere without feeling removed from everything. Greenport Village is about a 10 minute drive away, while Goldsmith’s Marina and Southold Fish Market are even closer. It’s the kind of house that feels easy. Morning coffee in the sunny dining nook, dinner outside on the deck, a walk down to the beach, then back home to the fire pit under the lights.

2 Beds ⋅ 1 Baths ⋅ 1050064 MLS

What surprised me is the option to consider a 2.7% assumable mortgage, a ownership member of the 2.5 acre beach and an updated home with updates and charm. The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling. Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just pours into the room. From there, everything connects. The dining area opens visually to the kitchen, where the sink sits under a window looking out toward the outdoor dining table, and the living room is right there too. You can literally be cooking, sitting at the table or relaxing on the sofa and still see the TV. It’s a really comfortable layout for everyday living. The two bedrooms are nicely separated into the sleeping side of the house with the full bathroom nearby. The larger bedroom easily accommodates a king size bed, and the second works perfectly with a queen, so it feels much more like a year round home than just a little summer cottage. But the backyard might be where I would spend most of my time. A deck runs along the length of the house with room for outdoor dining and seating, then there’s another spot with double lounge chairs where you could disappear with a book or just sit there and do absolutely nothing, which honestly sounds pretty good. At night, string lights run through the trees and completely change the atmosphere around the fire pit, with seating for six or more. Between the established plantings, mature trees and detached two-car garage, the backyard feels private, comfortable and finished. Then you discover Conkling Point Beach. The association provides access to this beautiful 2.5 acre crescent shaped sandbar just a few doors away. It has sandy beach, open water views toward The Pridwin and Sunset Beach on Shelter Island, and some incredible spots to settle in with your beach chairs beneath the windswept trees. With the breeze coming off the water and the sun dropping across the horizon, it can honestly feel like you found your own little island. What makes the location work so well is that you get that quiet beach community atmosphere without feeling removed from everything. Greenport Village is about a 10 minute drive away, while Goldsmith’s Marina and Southold Fish Market are even closer. It’s the kind of house that feels easy. Morning coffee in the sunny dining nook, dinner outside on the deck, a walk down to the beach, then back home to the fire pit under the lights.

738 Conklin Road, Greenport

1100 (aka 702 Linnett) 7th Street, Greenport

$899,000

Charming Cedar Shake Cottage on a Desirable Corner Lot. Enjoy it Now, and/or Expand Extensively in the Future with Proper Permits. The Spacious Deck, Brick Patio, Mature Landscaping, and Lush Shrubbery Create a Private and Secluded Backyard Retreat. Just 3–4 blocks to Beautiful Bay Beaches and 6 Blocks to Greenport Village, Marina, Shops, Restaurants, and NYC Transportation. Start Living the Good Life in Greenport Now. 1100 7th Street, Greenport is also known as 702 Linnet Street, Greenport.

1 Beds ⋅ 1 Baths ⋅ 1004839 MLS

Charming Cedar Shake Cottage on a Desirable Corner Lot. Enjoy it Now, and/or Expand Extensively in the Future with Proper Permits. The Spacious Deck, Brick Patio, Mature Landscaping, and Lush Shrubbery Create a Private and Secluded Backyard Retreat. Just 3–4 blocks to Beautiful Bay Beaches and 6 Blocks to Greenport Village, Marina, Shops, Restaurants, and NYC Transportation. Start Living the Good Life in Greenport Now. 1100 7th Street, Greenport is also known as 702 Linnet Street, Greenport.

1100 (aka 702 Linnett) 7th Street, Greenport

How much is your home worth?

How much is your home worth?