Greenport Homes with Landscaped Lot features

Welcome to Greenport, a picturesque gem nestled on the North Fork of Long Island, New York. This charming village, located in Suffolk County, boasts a rich maritime history and a vibrant arts scene, making it a delightful place to call home. With its stunning waterfront views, historic architecture, and a close-knit community, Greenport offers an idyllic lifestyle that perfectly balances relaxation and recreation.

One of the standout features of homes in Greenport is their beautifully landscaped lots. Imagine waking up each morning to the sight of lush gardens, vibrant flower beds, and meticulously maintained lawns, all set against the backdrop of the stunning Long Island Sound. These outdoor spaces not only enhance the aesthetic appeal of your home but also provide a tranquil retreat for enjoying warm summer evenings or hosting gatherings with family and friends.

Greenport is not just about scenic beauty; it’s also a hub for local culture and cuisine. The village is home to charming boutiques, art galleries, and an array of restaurants that celebrate the region's fresh seafood and farm-to-table offerings. Whether you’re strolling along the historic streets or enjoying a sunset at the local marina, Greenport exudes a sense of community and charm that is hard to resist.

With a variety of homes featuring landscaped lots, Greenport provides the perfect canvas for creating your dream outdoor oasis. Whether you prefer a cozy cottage or a modern estate, you’ll find properties that reflect the essence of this enchanting village. Discover the magic of Greenport, where your ideal home awaits amidst stunning natural beauty and a vibrant community spirit.

Newest Greenport Homes with Landscaped Lot features

$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

$2,995,000

7 Beds ⋅ 7 Baths ⋅ 1016379 MLS

UNDER CONSTRUCTION - IN PHASE 3 - PROPERTY IS CLOSED IN, ROUGHED IN AND CLOSING IN WALLS - NOW AVAILABLE FOR PRIVATE IN PERSON VIEWINGS - Introducing an exceptional opportunity to own a brand new construction home in Greenport’s coveted Eastern Shores where North Fork charm meets modern luxury living. Don't miss this opportunity to claim for yourself this thoughtfully designed, currently under construction and anticipated to be completed summer 2026 in time for your East End getaway. This stunning seven bedroom six and half bath residence offers 4,544 sqft of refined living space designed with no desire left unrecognized. From the moment you arrive, you’ll appreciate the timeless architectural detail, modern farmhouse feel with a blend of contemporary finishes throughout. The open concept is ideal for entertaining featuring a chefs kitchen with oversized island, premium appliances, abundant cabinet space and butler pantry all flowing effortlessly into the spacious living room, formal dining room or out to the rear covered porch. Seven generously sized bedrooms include an expansive primary suite with oversized bathroom, walk in closet and private second story deck overlooking the backyard. Four of the bedrooms including the primary are on the second level, one bedroom on the main level and two bedrooms are located in the lower level all situated with their own respective bathrooms with the mindfulness around a main level bedroom with en suite full bath. Additional features in the build include a finished walk out lower level with recreational room, in ground vinyl pool and a detached two car garage. This beautifully crafter modern farmhouse is situated between the tranquil Inlet Pond and the beloved Kontokosta Winery also just minutes from the vibrant downtown of Greenport Village. This property is located on the north end of Tasker lane alongside a cleared public pathway with just a 2 minute walk to the famed 67 Step Beach of Greenport. Whether you’re seeking a year round residence, a second home or a vacation rental investment, 1050 Tasker Lane delivers a rare combination of location, luxury, and lifestyle on the North Fork.

1050 Tasker Lane, Greenport

$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

$1,459,000

3 Beds ⋅ 2 Baths ⋅ 983029 MLS

Water view meticulously renovated 3 bedroom 2-bath corner home in Greenport, offering privacy with a landscaped fenced-in garden. A true sanctuary, a large side open spacious garden with mature trees and an intimate private patio that overlooks the picturesque Sterling Harbor, alive with sailboats and fishing vessels. This thoughtfully renovated home has been thoroughly rebuilt, showcasing its architectural charm including pine flooring and a classic front porch. The lower level boasts an open-concept kitchen and living area, complemented by a sun-drenched room with water views, separated by pocket doors, ideal for a formal dining room or a versatile third bedroom. A full bath on this level adds convenience. Upstairs, you'll find two comfortable bedrooms and a dedicated small office area, all overlooking the serene rear garden and harbor. A second full bath completes the upper floor. There is also a full attic and a separate one car garage that is ideal for a possible future accessory housing unit and/or a great workshop equipped with its own 100 amp electric service. A pool or a rear extension are both possible options for a future owner. An Easy walk to the Greenport Village, or 15 minute walk to the Peconic Bay Manhasset Beach or to the LI Sound 67 steps Beach.

412 Atlantic Avenue, 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

$1,350,000

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

$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

$895,000

922861 MLS

Beautifully renovated historic building in the heart of Greenport Village’s commercial district. This light-filled, two-story property has been home to the well-established VSOP Projects art gallery for the past eight years and offers a versatile layout well-suited to a range of uses, presenting an exciting opportunity for its next entrepreneur or investor. Stunning original wide-plank floors and a large whimsical rear garden pair seamlessly with a full slate of recent upgrades, including new electrical, HVAC, windows, insulation, siding, and lighting, creating a truly turn-key space. Ideally situated just one block from the Jitney, LIRR, Shelter Island Ferry, multiple hotels, and municipal parking, and surrounded by Greenport’s vibrant shops, restaurants, and waterfront.

311 Front 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.