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$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
$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
$2,950,000
989877 MLS
Greenport's premier Front Street address. High-visibility mixed-use building featuring in-place income and 2,912 square feet available for immediate use. Positioned on the village's busiest corridor with constant foot traffic from tourists, boaters, and ferry passengers. Existing cash flow with clear upside in the North Fork's most sought-after retail location.

38-44 Front Street, Greenport
$1,800,000
1008060 MLS
2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!

69430 Main Road, Greenport
$799,000
3 Beds ⋅ 1 Baths ⋅ 1028101 MLS
Super Cute Greenport Village home packed with charm and character. Walking distance to downtown. 3 bedrooms, 1 bath, diving area, kitchen and living area all on 1st floor with 3 bedrooms and a full bathroom above. Full walk out Basement and fenced in yard. Close to downtown Greenport, Marinas, Golf, restuarants and wineries.

308 Monsell Place, Greenport
$1,385,000
4 Beds ⋅ 3 Baths ⋅ 1023884 MLS
Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

4408 Old North Road, Southold
$699,000
1006809 MLS
Excellent opportunity! Attention investors! vacant commercial shy acre lot in high traffic location Dec approval

8155 Route 25, Mattituck
$859,900
3 Beds ⋅ 2 Baths ⋅ 960613 MLS
PRICE IMPROVEMENT!! Whether year-round living or a summer getaway, do not let this one "Get Away"! Located on the much-desired Gull Pond Lane, this classic ranch-style home presents a rare opportunity to create your North Fork Dream. Architectural design plans for renovation are available to view. This home features freshly refinished hardwood floors, 3 bedrooms, 1 newly updated full bath, one primary suite half bath, a formal dining room, a spacious and inviting living room with a wood burning fireplace, large picture window and custom built-ins, a whole house standby generator and a full basement with endless possibilities. Updates also include Hot Water Tank, CAC, Electrical Service and most windows. Set on a generous-sized private lot, it is the perfect setting for quiet times or outdoor entertaining. Conveniently located, this hidden gem is near Greenport Village shops, award-winning restaurants and wineries, marinas, farm stands, Island's End Golf & Country Club, Shelter Island Ferry and beaches. This fabulous home is being sold as-is. Make it the sanctuary where your history continues.

290 Gull Pond Lane, 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
$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
$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
$1,675,000
837908 MLS
Nestled in the bustling heart of Mattituck, this exceptional commercial property offers the perfect blend of retail space and residential income opportunities. Already home to a successful business, this fully leased building is zoned for Hamlet Business. The prime location provides incredible potential for a variety of businesses, while generating consistent income from its two fully-leased, income-producing apartments above.

13100 Main Road, Mattituck
$1,675,000
3 Beds ⋅ 4 Baths ⋅ 837910 MLS
Nestled in the bustling heart of Mattituck, this exceptional commercial property offers the perfect blend of retail space and residential income opportunities. Already home to a successful business, this fully leased building is zoned for Hamlet Business. The prime location provides incredible potential for a variety of businesses, while generating consistent income from its two fully-leased, income-producing apartments above.

13100 Main Rd, Mattituck
$2,599,000
4 Beds ⋅ 3 Baths ⋅ 862263 MLS
Soundfront! Welcome to 2100 Sound Drive - offering water views from nearly every room, this unique property is part of the Eastern Sterling Shores community and is truly the Last of the Mohicans! Greeted by a welcoming circular driveway and situated atop a picturesque bluff, you'll enjoy captivating views and summer breezes. Stairs lead to an enchanting enclosed bungalow while your own private oasis awaits beyond and within just 40' of this pristine property are bountiful fish and lobster, ideal for the fishing enthusiast. At the center of this entertainer’s delight is an oversized living room accented with dramatic beamed ceilings, a stone wood-burning fireplace and custom built-ins. Four bedrooms, three full baths as well as an eat-in kitchen, formal dining room, all-season room, huge rear patio and attached 2-car garage, complete this special home. Located just a stone's throw to Greenport Village with fine-dining, shopping and ferry access, don't miss this incredible opportunity! Property sold as is.

2100 Sound Drive, Greenport
$2,100,000
5 Beds ⋅ 5 Baths ⋅ L3579812 MLS
This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

151 Bay Avenue, Greenport
$2,850,000
L3579804 MLS
Greenhill Kitchen - an updated two-story restaurant with the best commercial location on the corner of Front Street and First Street in the heart of downtown Greenport Village. Established restaurant with two indoor bars, live music stage and an outdoor tiki bar. There is ample seating on both floors, indoors and outside on the large upper deck. This Front Street location offers superb visibility and high foot traffic with Mitchell Park carousal and marina across the street. Greenport is a thriving Village year round, drawing in both tourists and North Fork residents with events and parades such as; Tall Ships, The Maritime Festival, Presidents Parade, Cherry Blossom Festival, Halloween, The Christmas Tree Lighting, The Easter Egg Roll, The Cherry Blossom Festival and Shellabration, just to name a few. This is an amazing opportunity!

48 Front Street, 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.