Greenport Homes with Sprinklers In Front Lot features

Welcome to the charming community of Greenport, nestled in the heart of Suffolk County, New York. Known for its picturesque waterfront and vibrant downtown, Greenport offers a unique blend of small-town charm and coastal allure. One of the standout features of this area is its exceptional school district, which is dedicated to fostering a nurturing and enriching environment for students. The Greenport School District prides itself on its strong academic programs, dedicated faculty, and a commitment to extracurricular activities that promote well-rounded development. Families moving to Greenport can rest assured that their children will receive a quality education in a supportive community.

In addition to its educational offerings, Greenport is home to a variety of beautiful properties, including homes with sprinklers in the front lot. These charming residences not only enhance the curb appeal of the neighborhood but also provide practical benefits for homeowners. Imagine stepping out of your front door to a lush, green lawn that is effortlessly maintained with a well-designed sprinkler system. This feature allows you to enjoy your outdoor space without the hassle of manual watering, giving you more time to savor those idyllic summer evenings by the water.

Whether you're drawn to the excellent schools, the welcoming community, or the beautiful homes, Greenport is a place where memories are made. Explore the properties that await you in this delightful coastal town and discover the perfect place to call home.

Newest Greenport Homes with Sprinklers In Front Lot features

$2,200,000

5 Beds ⋅ 4 Baths ⋅ 1043780 MLS

Immeasurable charm in the heart of Greenport Village. Beautifully updated while retaining much of its historic character, the main house features three bedrooms and three full baths, a handsome kitchen flooded with natural light, high ceilings, restored pocket doors, and original period moldings. At the rear of the property, a charming two-bedroom guest cottage with a full bath and kitchen provides wonderful flexibility for hosting or additional living and work space. Outside, the pool is tucked into beautifully established gardens, complemented by a bluestone patio and extensive mature landscaping that give the property a remarkable sense of privacy and place. All of this just moments from Greenport's downtown waterfront and some of the North Fork's best restaurants, shops, and waterfront destinations, with beaches, farm stands, and vineyards all within a mile.

611 1st Street, Greenport

$4,500,000

3 Beds ⋅ 2 Baths ⋅ 1047292 MLS

At the end of a secluded, private one-mile road, where the land meets the Long Island Sound, this newly renovated modern beach house offers breathtaking views, refined design, and total privacy. Set on two-thirds of an acre and surrounded by two 30 acre privately owned parcels of land, one of which is entirely vacant, the home features over 100 feet of private beachfront with a naturally sloped path leading to the shore. Every inch of this residence is bathed in natural light and designed to celebrate its stunning surroundings—from the expansive great room with white oak flooring and gas fireplace to the vaulted dining area and sleek kitchen with a gas stove and integrated workspace. The primary suite includes a spa-inspired bath with a sauna, shower, and bidet, while the additional first floor bedroom has an en-suite bathroom with a second floor bedroom as well. There is a full fitness center in a finished basement with heat and central air conditioning with walk out stairs to the pool area. All new Pella black-framed windows perfectly frame the Sound, with nearly every room offering unobstructed water views. Outside, lush landscaping and vibrant hydrangeas surround a 50’ x 8’ heated saltwater gunite pool with an automatic cover and stone patio, creating a peaceful outdoor retreat ideal for both entertaining and everyday living. The white board and batten siding, matte black metal roof, and detached one-car garage complete the clean, modern aesthetic. With porcelain tile sunroom floors, low taxes, and deeded road rights with private gate, this is a rare opportunity to own a fully renovated waterfront home with unrivaled serenity, where the sunsets, sea breeze, and silence feel like your own private oasis.

38099 Main Road, Orient

$1,595,000

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

$2,249,000

4 Beds ⋅ 4 Baths ⋅ 1032350 MLS

Welcome to this exceptional estate, just a short walk from a private deeded beach and dock. Designed for entertaining, this spacious property features an impressive outdoor living area complete with a covered, built-in bar and kitchen—perfect for hosting family and friends. Enjoy the quiet, peaceful surroundings while still being close to everything you need. With low taxes and move-in-ready condition, this home offers the ideal combination of comfort and convenience. Furniture is negotiable, and the property may be sold furnished.

705 Gus Drive, East Marion

$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

$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

$1,276,000

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

$1,529,000

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

$2,900,000

5 Beds ⋅ 5 Baths ⋅ L3528746 MLS

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a "to be built" opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

150 N Hillcrest Drive, Orient

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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.