Refine Search
Map
Sort by
2737 Rocky Point Road, East Marion
$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
775 Mulford Court, Orient
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 1051631 MLS
Set on a private .98-acre lot at the end of a cul-de-sac, this spacious 4-bedroom, 3.5-bath traditional home, built in 2003, offers approximately 2,900 sq. ft. of comfortable living space. The inviting interior features hardwood floors, an eat-in kitchen with Sub-Zero refrigerator, Wolf range, soapstone countertops, kitchen island and pantry, formal dining room, living room with wood-burning fireplace, mudroom, home office, and first-floor bedroom with nearby half bath. Upstairs, enjoy a family room with fireplace, luxurious primary en suite with Jacuzzi tub and separate shower, two guest bedrooms and additional guest bath. Outside, a fenced rear yard features a heated in-ground pool and bluestone paver patio—perfect for entertaining and summer enjoyment. Additional amenities include a one-car attached garage, whole-house water filtration system, home security system, and deeded beach rights. A wonderful opportunity to enjoy the Orient lifestyle in a beautiful private setting.

775 Mulford Court, Orient
2655 Rocky Point Road, East Marion
$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
80 Rabbit Lane, East Marion
$1,499,000
3 Beds ⋅ 2 Baths ⋅ 1031857 MLS
Experience waterfront living at its finest, in this exceptional cottage located directly on the Bay. This turn-key, one of a kind property, offers gorgeous water views and open concept living. The dramatic vaulted ceilings with exposed beams, create a stunning focal point, adding warmth, texture, and character throughout the living space. Step outside to your own private beach; perfect for swimming, kayaking, paddle boarding, boating, entertaining, or simply relaxing with your feet in the sand. The panoramic views create an unmatched open-bay lifestyle. Wake up each morning to the soothing sounds of the bay and breathtaking sunrises over the water, just steps from your door. This 3 bed 1.5 bath is waiting for you. Located in peaceful East Marion, this home has close proximity to the Jitney, LIRR, amazing restaurants, and the best vineyards the North Fork has to offer. Simply arrive, unwind, and enjoy the waterfront lifestyle you've been dreaming of.

80 Rabbit Lane, East Marion
1760 Albertson Lane, Greenport
$1,499,000
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
430 1st Street, Greenport
$1,495,000
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
1900 Gillette Drive, East Marion
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 909423 MLS
Modern Design Meets Coastal Living Welcome to your brand-new custom build in East Marion-crafted with an eye for detail and built for everyday luxury. This 4-bedroom, 3.5-bath home, complete with a spacious primary en-suite, balances timeless design with modern conveniences in a coveted beach community. Step inside to soaring ceilings, red oak select flooring, and Allwood custom cabinetry anchored by sleek quartz countertops. The kitchen is a chef's dream, featuring a Galiano Moena 36" gas range, double electric wall ovens, and a 24" wine cooler-because hey, why not! Light-filled spaces flow seamlessly to the outdoors, where a custom 18x36 Gunite saltwater pool (heated, of course) promises endless summers. Porcelain stone pavers and a generous patio set the stage for entertaining or unwinding after a swim. Additional highlights include cedar shake siding with a metal and asphalt roof, and a fully finished basement offering flexible space for media, fitness, or guests. It's not just a house-it's a backdrop for life at the beach. The right blend of craftsmanship, convenience, and coastal attitude. Could be you!

1900 Gillette Drive, East Marion
39595 Main Road, Orient
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 1061683 MLS
This Traditional 4-bedroom, 2.5-bath home sits near Orient State Park and the Cross Sound Ferry. The private, landscaped backyard has a heated pool and patio, plus a large deck with glass doors to the open-plan kitchen and family room, making it ideal for entertaining. The first floor is completed with a private living room, a dining room, laundry, and a powder room. Upstairs, the primary ensuite has a full bath with views of the backyard and pool. Three more bedrooms and a full bath complete the second floor. The finished lower level offers a large recreation space. This home is ideal year-round living or for enjoying North Fork summers.

39595 Main Road, Orient
210 5th Street, Greenport
$1,310,000
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
402 5th Street, Greenport
$1,300,000
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
10940 Main Road, East Marion
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 982221 MLS
This ranch style home offers a blend of comfort, convenience, and opportunity. With three spacious bedrooms and three beautifully finished bathrooms, the home provides generous space for relaxation, work, or entertaining. The well-appointed kitchen features a stainless-steel appliance package, Quartz countertops, and a Thor range and hood, combining style with functionality. The homes’ living room with wood-burning fireplace, creates a warm and welcoming atmosphere throughout the seasons, while the enclosed sunroom fills the home with natural light and is the perfect setting for year-round enjoyment. Set on a generous .63 acre lot, the property also offers a detached garage that adds valuable storage and workspace as well as ample room for a pool. Located in the vibrant community of East Marion, this home is in close proximity to local eateries, parks, beaches and other recreational amenities. Do not miss the chance to explore all the possibilities this special property has to offer.

10940 Main Road, East Marion
407 Wiggins Street, Greenport
$1,297,000
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
401 Wiggins Street, Greenport
$1,297,000
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
550 Madison Avenue, 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
515 The Greenway, East Marion
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 1039485 MLS
Classic Georgian Colonial set on approximately 0.47 acres, enhanced by mature spruce trees that offer natural privacy. The first floor features a welcoming living room with brick fireplace, formal dining room, family room, eat-in kitchen, conveniently located powder room, and access to the one-car garage. Upstairs are three bedrooms, including a spacious primary suite with private bath and large walk-in closet, plus two additional bedrooms sharing a full hall bath. A full basement with a separate entrance provides additional space and flexibility. A wonderful opportunity offering a traditional layout, generous property, and timeless Colonial character.

515 The Greenway, East Marion
East Marion
$1,249,000
3 Beds ⋅ 4 Baths ⋅ 1028434 MLS
Stylish Heritage Farmhouse: Dating to approximately 1910, this beautifully reimagined Queen Anne–inspired country home preserves a tangible connection to East Marion’s past. Set along the historic route once known as Kings Highway and Sunset Trail—today’s Main Road—and near Marion Lake, the residence was built when the hamlet still reflected its longstanding agricultural and maritime heritage while emerging as a sought-after North Fork summer retreat. Comprehensively renewed for contemporary living, the home pairs early-20th-century character and gracious proportions with refined interiors and exceptional outdoor potential. All major systems have been updated, offering the comfort, convenience and confidence of a modern residence within a home of enduring character. Privately situated behind stylish gates on a level, sun-filled half-acre, the property offers turnkey living in a thoughtfully landscaped setting. A welcoming wraparound porch opens to a beautifully appointed kitchen featuring stainless-steel appliances, quality finishes and sophisticated details. The open-concept living and dining areas flow naturally from the kitchen and extend to an open-air deck overlooking the expansive backyard. An existing pool permit provides an exciting opportunity to create a private outdoor retreat, while one of the property’s two substantial sheds could potentially be converted into a pool house, subject to applicable permits and approvals. The first-floor primary suite includes a beautifully finished bath with a soaking tub, while a separate powder room serves guests. Upstairs, two additional en-suite bedrooms each feature a thoughtfully designed full bath. Generous proportions continue throughout the home, with the basement providing abundant storage and a spacious laundry room. Propane heat and new central air conditioning ensure year-round comfort. The home’s flexible layout and peaceful yet convenient location also create an ideal live-work environment for remote professionals, digital nomads and those seeking a sophisticated country escape without sacrificing modern connectivity or convenience. Low East Marion taxes, two large sheds and mature landscaping further distinguish the offering. Ideally located minutes from Long Island Sound and Peconic Bay beaches, Marion Lake for kayaking and birdwatching, and the shops, restaurants and waterfront attractions of Greenport Village—with ferry connections to Shelter Island and the Hamptons—this stylish heritage farmhouse presents a rare opportunity to embrace four-season North Fork living and establish your own enduring North Fork legacy.

East Marion
295 Willow Terrace Lane, Orient
$1,230,000
4 Beds ⋅ 2 Baths ⋅ 995799 MLS
Wake up to the sound of gentle waves and breathtaking sunrises over Gardiner Bay in this charming four-bedroom, two bath coastal retreat. Nestled in the heart of Orient, this home blends classic North Fork charm with modern comforts. Step inside to find a bright, airy interior with open-concept living spaces, hardwood floors, and windows that capture stunning water views. The spacious kitchen offers ample counter space and flows seamlessly into the dining and living room areas, perfect for entertaining. Outside, enjoy a private porch overlooking the bay and a short stroll to a private sandy beach and Orient’s quaint village. Whether as a year-round residence, weekend escape or investment property, this gem offers the best of the North Fork.

295 Willow Terrace Lane, Orient
3825 Stars Road, East Marion
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 1053439 MLS
Located in the Stars Beach Community, this charming 3-bedroom, 2-bath cottage offers the perfect opportunity to create your own beach-town escape, weekend retreat, or year-round home. Chill in your backyard, lounge in your pool or enjoy the neighborhood beach and stay to watch the spectacular sunset then rinse off the sand in your outdoor shower. Enjoy cozy evenings by the wood burning fireplace or stay cool with central AC. Includes finished basement with outside access, garage, accessory shed, solar. Moments from North Fork's celebrated farm stands, restaurants, marinas, boating, award-winning wineries, and charming local shops. A true North Fork lifestyle opportunity in a wonderful beach community-come make it yours.

3825 Stars Road, East Marion
1405 Village Lane, Orient
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 1052203 MLS
A beautifully preserved 19th-century Victorian home set in the heart of Orient Village. The large screened three-season porch opens onto a picturesque rear garden, perfect for entertaining. A detached garage, recently renovated with heat, A/C, and EV charging — currently an art studio, but fully functional as a garage with intact new garage doors. The first-floor features custom cabinetry, a formal dining room, original radiators, a powder room, and the screened porch. Upstairs are two bedrooms and a full bath. Both the front and rear gardens have been professionally landscaped. Just steps from the post office, Country Store, yacht club, marina, and bay and sound beaches.

1405 Village Lane, Orient
8440 Main Road, East Marion
$1,199,000
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
25105 Main Road N, Orient
$1,189,000
4 Beds ⋅ 4 Baths ⋅ 1051989 MLS
Welcome to this wonderful circa 1890s 2-family farmhouse in the beautiful hamlet of Orient! Pristine and updated with the antique feel of yesteryear! The main home has 4 bedrooms 2.5 baths with wide planked wood floors and original moldings. The eat-in wainscot kitchen with new appliances has plenty of cabinetry and counter space. The formal dining room and spacious living room with fireplace easily open to the covered wrap around front porch overlooking flowering gardens and the lush grassy yard- a perfect retreat for entertaining, or sipping your morning coffee or tea. An ensuite bedroom on the 1st level, plus 2 bedrooms, an office/den and hallway bath upstairs. The 3rd level full attic has plenty of room for storage and possible future expansion. The attached 1-bedroom apartment features its own private entrance with a delightful screened-in porch, an open living, dining and kitchen space, and an ensuite bedroom. The beautiful side yard has room for vegetable and flower gardens, and there is a small shed for garden tools in the backyard. Come experience the peaceful North Fork life in this quintessential farmhouse. You will be just a few blocks from the historic village of Orient and town beaches. Savor the unspoiled beauty and nature in Orient. This home is move-in ready, and awaits your special touch!

25105 Main Road N, Orient
130 Tasker Lane, Greenport
$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
380 Homestead Way, Greenport
$1,149,900
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
216 Monsell Place, Greenport
$1,100,000
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
435 Sound Road, Greenport
$1,100,000
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
336 2ND Street, Greenport
$999,750
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
136 Bayview Avenue, Southold
$999,000
2 Beds ⋅ 1 Baths ⋅ 1017744 MLS
The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming right out your back door. Surrounded by the gorgeous Southold beaches, over 40 wineries, and local farms, the North Fork has it all. Make it a vacation or year-round home, this is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, Southold
1115 Willow Terrace Lane, Orient
$995,000
1006014 MLS
Beautiful .6 acre, waterview building lot on Willow Terrace in Orient. Deeded bay beach a few doors down. Walking distance to Orient village and Yacht Club. Close to sound beaches and North Fork amenities. Design plans in place for a 4 bed, 4.5 bath cedar shingled home. Septic design complete and Health Department permits in process.

1115 Willow Terrace Lane, Orient
395 Uhl Lane, Orient
$950,000
2 Beds ⋅ 2 Baths ⋅ 1035706 MLS
Orient By The Sea —North Fork living at Its Best- Located in the sought-after Orient By-The-Sea community, this charming two-bedroom, two-bath expanded ranch offers the ease of one-level living on a private, level, shy-acre property. With a deeded association beach and park just around the corner, this is a wonderful opportunity for both year-round and vacation living. The spacious, light-filled great room is the center of the home, with doors opening to an expansive patio with a retractable electric awning. Designed for outdoor living and entertaining, this inviting space overlooks the landscaped, park-like grounds and offers ample room for a swimming pool. The interior features two bedrooms and two full baths, including one with a generously sized walk-in shower. Additional living spaces include a welcoming dining room, comfortable living room, updated kitchen with a breakfast nook, and convenient laundry access. The home’s easy layout and abundance of natural light create a warm and inviting atmosphere throughout. The 1-car garage offers space for storage or future expansion. Enjoy all that Orient and the North Fork have to offer, with the Cross Sound Ferry, Orient State Park, and Duryea’s Restaurant just minutes away. The beautifully maintained association sound beach is a neighborhood treasure, featuring a stone path and picnic area, perfect for relaxing by the water, gathering with friends and family, and enjoying spectacular North Fork sunsets. A special opportunity to live, relax, and enjoy the North Fork lifestyle in one of Orient’s most desirable communities.

395 Uhl Lane, Orient
738 Conklin Road, Greenport
$925,000
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

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.

How much is your home worth?

Get instant property value now!