Greenport Homes for Sale

Welcome to Greenport, a picturesque gem nestled on the North Fork of Long Island, New York. This charming village in Suffolk County offers a delightful blend of coastal beauty and small-town charm, making it a sought-after destination for homebuyers seeking a serene lifestyle. With its rich maritime history, Greenport boasts a vibrant waterfront, where you can enjoy stunning views of the Peconic Bay, indulge in fresh seafood, or embark on a scenic ferry ride to Shelter Island.

As you explore the neighborhood, you’ll find an array of boutique shops, cozy cafes, and excellent restaurants that reflect the local culture and community spirit. The lively Greenport Village is a hub of activity, hosting seasonal festivals, farmers' markets, and art shows that bring residents together. Outdoor enthusiasts will appreciate the nearby beaches, parks, and vineyards, making it easy to soak up the natural beauty that surrounds this charming locale.

When it comes to homes for sale in Greenport, you’ll discover a diverse selection that caters to various tastes and budgets. From historic Victorian houses with captivating architecture to modern coastal cottages with stunning bay views, there’s something for everyone. Many properties feature spacious yards, ideal for entertaining or gardening, while others offer easy access to the water for boating and fishing enthusiasts.

Living in Greenport means embracing a lifestyle filled with leisure and community. With its welcoming atmosphere and an array of amenities, this enchanting village is not just a place to live; it’s a place to thrive. Come and explore the homes for sale in Greenport, and find your perfect slice of paradise on Long Island!

Newest Greenport Homes for Sale

$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

$1,095,000

3 Beds ⋅ 2 Baths ⋅ 1021578 MLS

Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport.

217 Center Street, Greenport

$799,900

3 Beds ⋅ 2 Baths ⋅ 1010914 MLS

Renovated 1910 Colonial with Open Floor Plan. Down the Road From Town Beach. Just a Short Bike Ride to Down Town Greenport and Wineries !! Possibility of Selling Fully Furnished !! Large Back Building Could Be Turned into a Pool House, Garage or Shed, Additional information: Appearance Diamond, Interior Features: Living Rm, Dining Area, Spacious Eat in Kitchen with Large Island, Breakfast Nook, 3 Bedrooms(Small one on First Floor, 2 On 2nd Floor), 1.5 Renovated Bathrooms. Separate Hotwater Heater, 2 Separate Driveways SELLER IS APPLYING FOR PERMIT AND VARIANCE FOR A INGROUND POOL, HE IS SELLING WITH PERMIT ONLY FOR IT NOT INSTALL.

275 Sound Road, Greenport

$1,579,000

3 Beds ⋅ 2 Baths ⋅ 1008089 MLS

A Turn of the century well preserved 3 BR 2 Bath period home in the sought after Greenport Village. A spacious parcel with a two car garage, a secluded peaceful garden, work shed and a large private rear deck. The interior features include a formal dining room, a large kitchen with cathedral ceilings, a newly renovated bath, original pine flooring, and a delightful sun room, plus the classic front porch. All In close proximity to the Village beaches, Peconic Bay and transportation to NYC. This property is ready to welcome the next resident.

311 5th Street, Greenport

$1,175,000

4 Beds ⋅ 2 Baths ⋅ 985147 MLS

Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept kitchen seamlessly connects to the living room. Large bedrooms, convenient first-floor laundry and home office complete the interior. The breathtaking backyard steals the show, with a stunning inground pool perfect for hot summer days, lush landscaping ensures privacy, making the firepit area a perfect spot for unwinding and enjoying outdoor serenity. The private community beach offers peaceful moments by the water. This location is ideal for sunset strolls or weekend fun., Additional information: Appearance:very good

130 Tasker Lane, Greenport

$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

$1,249,000

4 Beds ⋅ 2 Baths ⋅ 940213 MLS

* low-maintenance North Fork lifestyle, * weekend retreat, * turnkey without renovation headaches, * walkability, * lock-and-leave second home, * income potential, * simpler ownership vs larger estates “Freshly repositioned for the spring market, this beautifully renovated Village home offers exceptional value and immediate enjoyment. Featuring a complete renovation including new roof, siding, HVAC, appliances, and hardwood flooring throughout. The property also offers potential for additional living space—please discuss possibilities . Seller welcomes serious inquiries and will consider all reasonable offers .This home is ideally located just minutes from the heart of Greenport Village, offering access to the harbor, Mitchell Park, mass transportation and the waterfront, shops, restaurants, cafes, galleries, and the LIRR station, making this a convenient locations in the village. The property sits close to marinas, beaches, and ferry service to Shelter Island, and is close to the North Fork’s vineyards and farm stands. This location provides the perfect blend of quiet residential living” with all of Greenport’s amenities just minutes close. All information provided should be verified by the buyer, all information including but not limited to taxes, location, permits, square footage, should be verified by buyers. Equal housing opportunity

336 2ND 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

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

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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.