Homes for Sale in 11944

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.

Jules Zaphire Locqube New York, Inc.

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings,

William Walters Daniel Gale Sothebys Intl Rlty

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

Jerry Cibulski Century 21 Albertson Realty

Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor

Kris Pilles East End Luxury Ltd

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

Douglas Cabral Century 21 Excelsior Realty

Charming Greenport Village GetawayEnjoy the best of the North Fork from this inviting 3-bedroom, 2-bath home, perfectly located near all that Greenport Village has to offer. Stroll to Mitchell Park, waterfront dining, restaurants, shops, and the Shelter Island Ferry, or spend the day exploring nearby vineyards and Greenport Harbor Brewing Company.A wonderful opportunity to enjoy

Mary Terry MCKENNASHEA LLC

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

Barbara Poliwoda Douglas Elliman Real Estate

BRING ALL OFFERSGREENPORT, NY — RELAUNCHED UNDER $1 MILLIONLimited 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

Ron Moschetta Keller Williams Realty Greater

Greenport Gem — Timeless Elegance & Coastal LivingTucked privately behind tall hedges on a beautifully landscaped, gated corner property, this stately 1930s American Square offers an exceptional blend of historic character, refined comfort, and the coveted Greenport lifestyle.Meticulously restored in 2012 and gently lived in since, the home retains its original woodwork, doors,

Paul Loeb Douglas Elliman Real Estate

Charming Cedar Shake Cottage on a Desirable Corner Lot. Enjoy it Now, and/or Expand Extensively in the Future with Proper Permits. The Spacious Deck, Brick Patio, Mature Landscaping, and Lush Shrubbery Create a Private and Secluded Backyard Retreat. Just 3–4 blocks to Beautiful Bay Beaches and 6 Blocks to Greenport Village, Marina, Shops, Restaurants, and NYC Transportation. Start Living the Good

Paul Loeb Douglas Elliman Real Estate

Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable

Bridget Elkin Compass Greater NY LLC

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

Kristen Rishe Signature Premier Properties

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

William Walters Daniel Gale Sothebys Intl Rlty

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

Jerry Cibulski Century 21 Albertson Realty

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

John Quinn John Quinn Inc

GREENPORT, NY: Recently renovated farmhouse in a quiet neighborhood. 2 bedrooms 1 bath. Open concept, eat in kitchen, central air conditioning, washer/dryer, Gas grill, fire pit, dining /seating area, WiFi/cable. Close to downtown Greenport, beaches, wineries, and major North Fork attractions. Ready for Summer 2026! Exclusive: $895K.

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

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.

Janet Markarian Daniel Gale Sothebys Intl Rlty

North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This fully furnished Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort

Samantha Ripka RESOURCE REALTY GROUP

Greenport - Historic Colonial Farmhouse in Peconic Bay Estates.Offered for the first time in decades is this rare slice of Long Island history. Step back in time without sacrificing modern comfort in this circa 1600s, Dutch Colonial farmhouse, gracefully set on .39 acres in the heart of the North Fork. With 4-5 bedrooms, 3 full baths, and over 400 years of character, this one-of-a-kind home

Deirdre DeVita Sothebys Int'l Realty Hamptons

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

Alexis Meadows Compass Greater NY LLC

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

Donna Fakiris Modern Age Realty Group LLC

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

Bridget Elkin Compass Greater NY LLC

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

Jerry Cibulski Century 21 Albertson Realty

A Rare Opportunity!!! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long

Christopher Andron Andron Realty Group Tulip R E

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.

Isaac Israel Richmond Realty Corp

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,

Douglas Cabral Century 21 Excelsior Realty

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

Jennifer Benton Compass Greater NY LLC

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

Paul Loeb Douglas Elliman Real Estate

North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort setting, including a

Samantha Ripka RESOURCE REALTY GROUP

North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This fully furnished Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort

Samantha Ripka RESOURCE REALTY GROUP

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

Jill Dunbar Douglas Elliman Real Estate

North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort setting, including a

Samantha Ripka RESOURCE REALTY GROUP

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.

Paul Loeb Douglas Elliman Real Estate

Modern Log Home Retreat with Deeded Water Access & ADU Potential | Greenport, NY Discover a truly distinctive single-family modern log home set within one of Greenport’s most coveted peninsula locations. Built in 2003 and thoughtfully renovated in 2021, this 2,396 sq. ft. residence offers 4 bedrooms, 2 baths, and 9 well-proportioned rooms designed for comfort, privacy, and effortless indoor

Derek Greene Greene Realty Group

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

Diane Prudenti Coldwell Banker American Homes

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

Connie Liappas Compass

This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up!Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom

Justin Concannon Compass Greater NY LLC