Greenport Homes with Front Yard Lot features

Welcome to Greenport, New York, a charming village nestled in the heart of Suffolk County. Known for its picturesque waterfront views and rich maritime history, Greenport is not just a scenic getaway; it’s also home to an exceptional school district that prioritizes the education and well-being of its students.

The Greenport School District is renowned for its commitment to academic excellence and innovative teaching methods. With a focus on fostering a nurturing environment, the district offers a range of programs designed to cater to the diverse needs of its students. From advanced placement courses to vibrant extracurricular activities, Greenport schools aim to inspire young minds and prepare them for future success. The dedicated faculty and staff work tirelessly to create a supportive atmosphere, ensuring that every child feels valued and motivated.

In addition to its educational offerings, Greenport boasts lovely homes with front yard lot features that enhance the community's charm. Imagine stepping out of your door to a beautifully manicured lawn, where children can play and neighbors can gather. These homes not only provide a welcoming curb appeal but also foster a sense of community and connection among residents.

Living in Greenport means enjoying the perfect blend of small-town charm and modern amenities, all while being part of a nurturing educational environment. Whether you’re raising a family or looking to settle down in a vibrant community, Greenport offers a unique lifestyle that is hard to resist. Come explore the beauty of this coastal village and discover your dream home today!

Newest Greenport Homes with Front Yard Lot features

$8,400,000

6 Beds ⋅ 7 Baths ⋅ 964447 MLS

Rare opportunity to own a uniquely private 7.49-acre bay front estate in Orient Village. This exceptional waterfront property features a spacious 5700 sq ft main residence with 6 bedrooms, 7 baths, three wood burning fireplaces, three bay garage, expansive front and rear covered porches and panoramic bay views. The 20 x 44 heated pool is complemented with a 860 sq ft pool house featuring open common area, kitchenette, full bath, laundry, two changing rooms, outdoor shower, & porch – creating an ideal setting for entertaining and summer living. A fully fenced clay 60 x 120 ft tennis court is expertly sited, so sun glare is never an issue. The property offers an additional free-standing two-bay garage with second floor bonus space providing flexible options for recreation, boat/bike storage or studio space. The 195 ft wide private walkout bay beach offers sweeping Harbor views of Long Beach State Park, Bug Light House and Orient Yacht Club. The property is ideally located within walking or biking distance to the Village of Orient, Orient Yacht Club, local marinas, Post Office, the Country Store, Oysterponds Historical Society and all village amenities.

1600 King Street, Orient

$1,785,000

4 Beds ⋅ 3 Baths ⋅ 1027434 MLS

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

90 Caiola Court, Greenport

$6,000,000

3 Beds ⋅ 3 Baths ⋅ 1015950 MLS

Set on 9.1 remarkably private acres in one of Orient's most scenic and protected landscapes, this distinctive residence offers a rare combination of architectural character, beautifully developed grounds, and sweeping pastoral views across meadows, Hallock Bay, and Gardiners Bay beyond. Originally part of the historic Hallock farm, the property has been thoughtfully cultivated over decades. Specimen trees, extensive landscaping, and a pond create a setting that feels both intentional and deeply connected to the surrounding natural environment. The elevated position captures expansive vistas while preserving a remarkable sense of privacy. The cedar-clad home was designed to maximize natural light and take full advantage of its extraordinary surroundings. Floor-to-ceiling windows frame the landscape, while more than 1,000 square feet of porches and decking create a seamless relationship between indoor and outdoor living. Classical proportions are balanced by a contemporary coastal sensibility, resulting in a residence that feels timeless, comfortable, and distinctly North Fork. Outdoor amenities are equally compelling. A large gunite pool is set within a bluestone surround and complemented by a brick patio and pergola-covered terrace. The accessory building immediately adjacent incorporates a pool house, substantial loft space, and a two-car garage, providing flexibility for storage, recreation, or studio use. Located within the coveted Narrow River corridor, the property offers easy access to quiet beaches, exceptional wildlife viewing, and the marina, while remaining moments from Orient Village. Properties of this scale and setting rarely come to market, particularly in a location where protected landscapes and enduring views define long-term value.

4725 Orchard Street, Orient

$1,299,000

4 Beds ⋅ 2 Baths ⋅ 1021286 MLS

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

8440 Main Road, East Marion

$2,399,000

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

$2,700,000

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

$1,950,000

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

$1,529,000

4 Beds ⋅ 3 Baths ⋅ 961091 MLS

Experience the beauty of coastal living with this young Colonial built in 2006 and set on 1.2 verdant level acres of privacy and seclusion. The expansive front yard, complemented by a grand circular driveway, creates a lasting first impression. The welcoming covered front porch is perfect for sipping your morning coffee while the equally expansive rear yard is ideal for star gazing on warm summer evenings or hosting large gatherings. An open floor plan connects the living, dining and kitchen spaces offering seamless daily living and makes entertaining a breeze. Four generously-sized bedrooms including a substantial primary ensuite with jacuzzi and an additional hall bath, complete the second floor. There is unfinished attic space above the attached two-car garage and a full unfinished lower level with high ceilings which may provide a blank slate for even more living space. Located just down the road from renowned Rocky Point Rd. Beach, a fresh vegetable stand and fragrant lavender farm, this home is also just a stone's throw from convenient ferries, a myriad of wineries and acclaimed Greenport with world class dining. This gem offers a fantastic opportunity to enjoy all the North Fork is so well known for and more!

2655 Rocky Point Road, East Marion

$2,195,000

4 Beds ⋅ 4 Baths ⋅ 956958 MLS

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

1680 Lands End Road, Orient

$2,400,000

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

$749,999

5 Beds ⋅ 4 Baths ⋅ 898986 MLS

"Live Where Others Vacation" paired with "Approx. 2,800 Sq. Ft. of Finished Living Space" and "Minutes to LIRR". An exceptional opportunity to own in the highly sought-after Greenport / North Fork region, where lifestyle, flexibility, and long-term value come together. Whether you are seeking a "weekend getaway", "investment", "one of the North Fork's most desirable destinations", "year-round residence", "weekend retreat", "possibilities are endless", this well-maintained ranch offers outstanding versatility in one of Long Island’s most desirable coastal destinations. Welcome to 395 Linnet Street, also known as 806 Linnet Street. Designed for today’s casual lifestyle, the home features an open-concept layout, 3 bedrooms and 2 full baths, 1,400 square feet on the main level, along with an updated eat-in kitchen showcasing quartz countertops. The expansive backyard creates the perfect setting for entertaining, outdoor dining, or simply enjoying the peaceful North Fork atmosphere. The fully finished lower level [1,400 square feet] with outside entrance (OSE) offers additional bedrooms and baths (all on Certificate of Occupancy), creating exceptional flexibility for extended living, guests, private work-from-home space, recreation, or separate accommodations. Located just minutes from bay beaches, marinas, parks, vineyards, farm stands, acclaimed restaurants, boutique shopping, the historic Greenport waterfront village, LIRR, and Hampton Jitney, this property places you in the center of the North Fork lifestyle that continues to attract homeowners and weekend visitors alike. Minutes to Beaches, Vineyards & Greenport Village

395 Linnet Street, Greenport

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.