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410 6th Street, Greenport
$864,200
3 Beds ⋅ 2 Baths ⋅ 1041851 MLS
Built in 1910, this classic Greenport Village farmhouse offers something that is becoming increasingly hard to find in the Village by having an extra wide, extra deep lot with the space to truly create the backyard lifestyle you have been wanting. With an outdoor fireplace under the stars, long summer dinners, gardens, entertaining space, and afternoons spent soaking up the sun before heading down to 6th Street Beach at the end of the road to cool off with the breeze off the water. Inside, the home retains original woodwork and that inviting farmhouse feel. With a surprisingly adaptable floor plan this house has an open layout. The front living room flows through the dining room and into the large farmhouse kitchen, creating a direct sightline all the way to the backyard. Morning light fills the kitchen, which opens naturally to the outdoor space and makes the yard a great space for outdoor dinners after having lunch at the beach. A generously sized bedroom on the main floor is in demand, while the second level offers an excellent opportunity to create a modern primary en-suite. That adaptability is one of the property's strongest features. Many homes from the early 1900s have floor plans that can be difficult to rework, but this home offers a layout and lot size that provide far more freedom to personalize and improve. Then there is the location. From here, Greenport Village is yours to enjoy, with easy access to the movie theater, IGA, restaurants, shops, Mitchell Park and Marina, the waterfront, and the energy that makes this Village such a special place. For someone who appreciates original character but wants the opportunity to create a home around today's lifestyle, this is an exciting chance to reimagine a classic Greenport farmhouse and make it entirely your own.

410 6th Street, Greenport

311 Front Street, Greenport
$840,000
1060295 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

44 (1180) Sound Road, Greenport
$799,000
2 Beds ⋅ 1 Baths ⋅ 1035656 MLS
A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the façade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures — each equipped with electricity and water, and one including a bedroom — offer flexible space for guests, a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

44 (1180) Sound Road, Greenport

216 Broad Street, Greenport
$699,000
2 Beds ⋅ 1 Baths ⋅ 1047466 MLS
Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the "diamond in the rough" you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can't be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this in the heart of Greenport are few and far between, so don't let this one slip away.

216 Broad Street, Greenport

400 Aquaview Avenue, East Marion
$629,900
1038007 MLS
Welcome to 400 Aquaview Ave, East Marion, a rare opportunity to create your own North Fork retreat in desirable East Marion. Situated on approximately 0.56 acres, this vacant parcel offers a wonderful setting for those looking to establish a home in one of the East End’s most charming coastal communities. The lot sits around 150ft x 175ft affording ample space for a generous sized home, pool and outdoor entertainment space. The property fronts Aquaview Ave but also extends to Circle Dr W for if creating a nice private drive is in your vision. Surrounded by the natural beauty and relaxed atmosphere that define the North Fork, the property provides an exciting opportunity to bring your dream home to life. Just a short walk away you'll find access to sound beaches at the top of Rocky Point Road, Kontokosta Winery, Greenport Village, Orient Point Ferry and all the beauties of the North Fork.

400 Aquaview Avenue, East Marion

1080 9th Street, Greenport
$550,000
1055380 MLS
Discover the perfect opportunity to build your dream home on this beautiful 1.67-acre waterview lot in the heart of Greenport. Just five blocks from Greenport Village, you’ll have easy access to charming boutiques, renowned restaurants, lively bars, and more—all while enjoying the tranquility of your own private retreat. This property includes deeded bay beach rights at the end of 9th Street, where you can , take a refreshing swim, or set off on a peaceful kayak adventure around Pipes Cove. Please note: Showings are by appointment only. No one is permitted to walk the grounds without an agent present. Don’t miss this rare chance to own a prime piece of North Fork paradise! No one is permitted to walk the property without an appointment and must sign a Hold Harmless.

1080 9th Street, Greenport

11100 Main Road, East Marion
$549,000
909575 MLS
Imagine creating your own North Fork retreat in East Marion, where peaceful country roads, beautiful beaches, farm stands, vineyards and the vibrant waterfront village of Greenport are all just moments away. Final subdivision approval is already in place for this exceptional 42,000-square-foot homesite, offering a rare opportunity to bring a thoughtfully designed coastal residence to life in one of Southold Town’s most desirable settings. Generously sized and located in the R-40 Zoning District, the property offers the space and flexibility to envision a substantial two-story residence with 4+ bedroom potential, expansive indoor-outdoor living and room for many of the features that make North Fork life so special. Picture summer afternoons beside a private pool, evenings entertaining beneath the stars, a peaceful garden, studio or pool house, and recreational amenities such as a pickleball or tennis court.    Public water is available, and the property does not contain wetlands, access or setback issues—valuable advantages that allow a future owner to focus on the excitement of designing and building. The generous building envelope may accommodate a home of up to approximately 5,100 square feet, while the property’s 20% overall lot-coverage allowance provides additional possibilities for the residence and accessory improvements. Conceptual renderings and preliminary site ideas prepared by acclaimed North Fork-based Kramer + deConciliis Architecture illustrate one inspired vision: a refined modern coastal home shaped by natural materials, abundant glass and an effortless connection between indoor and outdoor spaces. The plans are conceptual, allowing the next owner the freedom to personalize the property and create a home that truly reflects their own style and way of life. Whether imagined as a year-round residence, a relaxing weekend escape or a thoughtfully considered luxury investment, this is more than simply vacant land—it is an invitation to create something lasting in the heart of the North Fork. With final subdivision approval, public water availability and an appealing East Marion, known for low taxes, location near Greenport, beaches and boating, this may be one of the most compelling building opportunities available in the Town of Southold. Buyer to perform their own due diligence to ensure their design plans and ideas meet Town of Southold and any other applicable code and permitting.

11100 Main Road, East Marion

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.

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