Greenport Homes with Pool

Welcome to Greenport, New York, a charming village nestled in the heart of Suffolk County, where coastal beauty meets a vibrant community spirit. Known for its picturesque waterfront, Greenport offers a unique blend of small-town charm and modern amenities, making it an ideal place for families and individuals alike.

One of the standout features of living in Greenport is the highly regarded school district. The Greenport School District is committed to providing a quality education that fosters academic excellence and personal growth. With dedicated teachers and a supportive environment, students are encouraged to explore their interests and develop their talents. The district prides itself on its strong community involvement, ensuring that education extends beyond the classroom and into the lives of families and residents.

In addition to its educational offerings, Greenport is also known for its stunning homes, many of which come with the luxury of a private pool. Imagine enjoying warm summer days lounging by your own pool, creating lasting memories with family and friends. These homes provide the perfect retreat after a long day, allowing residents to unwind in their own personal oasis. Whether you’re looking for a cozy cottage or a spacious family home, Greenport's real estate market offers a variety of options to suit your lifestyle.

With its exceptional schools, beautiful homes with pools, and a welcoming community atmosphere, Greenport is not just a place to live; it's a place to thrive. Come explore all that this lovely village has to offer!

Newest Greenport Homes with Pool

$1,675,000

4 Beds ⋅ 3 Baths ⋅ 1047439 MLS

Located in the quaint town of East Marion this beautifully appointed ranch offers effortless one level living. Set on an acre property, bordering preserved land, this renovated home has been thoughtfully designed with four bedrooms, two of which are ensuite and three full bathrooms. Step inside to an open, light-filled layout where the kitchen flows seamlessly into inviting living room with fireplace and a dining room with vaulted ceiling. There is also a seamless flow between indoor and outdoor spaces-Step outside to a manicured yard with a Gunite heated saltwater pool, a serene private fenced backyard bordering preserved land - a peaceful and tranquil retreat-just moments to Rocky Point Beach, Greenport Village’s shops, restaurants, transportation and the North Fork’s best wineries and farm stands. This is North Fork living at its finest.

2737 Rocky Point Road, East Marion

$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

$1,175,000

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

$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

$2,795,000

5 Beds ⋅ 5 Baths ⋅ 1018538 MLS

Set on 2.3 private acres just off one of the North Fork's most desirable waterfront streets, this brand-new cedar-shingled residence offers timeless design, generous proportions, and an enviable combination of privacy and convenience. Spanning three finished levels, the home features five bedrooms and five baths, with thoughtfully designed living spaces that balance everyday comfort with an optimal footprint for entertaining. Outside, a gunite pool is positioned within the expansive grounds, creating a private retreat surrounded by mature landscaping. The prime location is just a few hundred yards from Sound beach access and less than five minutes from Greenport Village and Orient's Village Lane. With acclaimed restaurants, marinas, farm stands, wineries, and golf all minutes away, you have incredible access while maintaining the peace and privacy that make this corner of the North Fork so special.

205 Kats Court, East Marion

$5,695,000

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

$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

$839,000

3 Beds ⋅ 3 Baths ⋅ 926613 MLS

Spacious Cape with Garage, Nice Yard and Inground Pool, Ideally Located Near a Memorable Long Island Sound Beach. The Property Backs Up to a Scenic Waterfront Vineyard with Tasting Room, While Greenport Marinas, Boat Launches, Village Shops and Restaurants Are All Nearby.

28 (aka 710) Sound Road, Greenport

Start Your Search

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.