ML# :813226   Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village’s most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 8 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan. Additional information: Appearance: New

ML# :892479   A Creative Sanctuary in the Heart of Greenport.Tucked away on a tree-lined street in one of the “prettiest towns in America” (Forbes), this Cape Cod-style, wood-shingled home offers a rare blend of charm, privacy, and proximity to everything that makes Greenport so desirable.Perfectly situated on a full acre of land, the backyard abuts 8 acres of preserved open space owned by the Town of Southold — a rare buffer that offers both tranquility and an enduring sense of privacy.It’s less than a 15-minute stroll to 67 Steps Beach on the Long Island Sound and the vibrant heart of the village — including shops, galleries, restaurants, the North Fork Arts Center / movie theater, and the Greenport LIRR. Just a short bike ride away are Norman Klipp Park/Gull Pond Beach, 5th Street Beach, and the waterfront Kontokosta Winery. You’ll also find several nearby noteworthy wineries and farm stands that define the North Fork lifestyle.Inside, the home features three spacious bedrooms and two recently-updated full bathrooms, along with a wood-burning fireplace and original 1956 details that exude character. A separate 400 sq ft studio/office with vaulted ceilings, skylight, and radiant heated floors offers the ideal space for creative work, yoga, or lounging.Out back, the private garden and gravel patio were designed by Manscapers NY and feel like an outdoor room — complete with lounge chairs, shaded dining under mature trees, string lights, and layers of thoughtfully placed perennials, ferns, and herbs. It’s the perfect spot to gather with friends, grill, or unwind and watch the sunset.Whether year-round or as a weekend retreat, this is a home that invites creativity, connection, and calm — all just minutes from Greenport Village and the sea.

ML# :3587738   Views that never end! Welcome to your picturesque beachfront retreat along the Long Island Sound, where breathtaking water views and private beach access create a serene escape. Enjoy year-round sunsets that will take your breath away. This charming home features a fantastic layout with sun-soaked, high ceilings in the great room, seamlessly connecting the eat-in kitchen, living room, and dining area. The large elevated waterside deck offers easy access, perfect for entertaining or simply soaking in the beauty of your surroundings. The main level accommodates two spacious bedrooms and a full bathroom, while the second level is dedicated entirely to a luxurious primary bedroom complete with an ensuite bathroom and a private waterside balcony-ideal for enjoying quiet moments overlooking the water. Don’t miss this incredible opportunity to own your slice of heaven on the North Fork!

ML# :3572634   This chic, stylish Greenport Village home, was built with a nod to the Brooklyn Brownstone. Stunning new construction features cedar shake shingles and an artisan’s touch throughout. Surrounded by comfort and convenience, including a built-in EV charging hookup, a gorgeous studio shed in the fenced and fabulously landscaped backyard. 3 spacious bedrooms, 3 1/2 baths, and an entertainer’s kitchen. This light-filled, sexy stunner is just a short stroll to the library, farmers markets and the many restaurants, bars, and charming shops of Greenport Village., Additional information: Appearance:MINT+++

ML# :869285   Welcome to August Acres – A Tranquil Retreat Near GreenportNestled just a short distance from the charming Village of Greenport. This colonial-style home offers a perfect blend of comfort and convenience. Situated in a quiet and serene location, this beautifully maintained property is move-in ready and ideal for both relaxation and entertainment.The first floor features a spacious living room, an inviting eat-in kitchen, a formal dining room, and plenty of closet space. A conveniently located laundry room and a half bath complete this level.Upstairs, the home boasts four generously sized bedrooms, including a primary suite with its own bath, along with an additional full bathroom.Step outside to enjoy a wonderful backyard—perfect for summer gatherings, outdoor dining, or simply unwinding in your own private retreat.The private association bay beach is a short distance from this home. It is wonderfully peaceful, with the soft sand beneath your feet and the waves gently lapping at the shore. The perfect spot to relax and soak in the beauty of the water.Don’t miss the opportunity to make August Acres your new home!

ML# :906377   This charming two-story home is perfectly situated just a quarter mile from the beach, offering an ideal blend of comfort and convenience. The open-concept first floor features a welcoming living area with a fireplace, an eat-in kitchen equipped with quartz countertops, a gas stove, and stainless steel appliances, as well as a formal dining room with sliding glass doors that open to a private backyard with ample space for a pool. The Town of Southold previously issued a building permit for a pool that has since expired. A half bathroom completes the main level.Upstairs, you’ll find three generously sized bedrooms and two full bathrooms, providing plenty of space for family and guests. Hardwood floors flow throughout the home, which is also equipped with central air conditioning for year-round comfort.Located less than a mile from Greenport Village, this home offers easy access to beaches, marinas, restaurants, wineries, and all the amenities the area has to offer. Whether you’re looking for a primary residence, a weekend retreat, or a seasonal getaway, this property is a wonderful opportunity to embrace North Fork living.

ML# :905052   Renovated 1910 Colonial with Beautiful 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

ML# :896713   Own a Rare Piece of Greenport’s Main Street History- Step into The Hommel House, a 3 bedroom cherished Greenport landmark built in 1903. This Craftsman beauty retains all of its original character—warm wood details, inviting light-filled rooms, and a sense of timeless grace—while offering thoughtful updates for today’s lifestyle. A welcoming cook’s kitchen sits at the heart of the home, and the newly refreshed primary bath echoes the original 1903 style, complete with a clawfoot tub. Lush plantings of Privet and Rose of Sharon create a sense of seclusion, making you forget you’re right in the heart of Main Street. In summer, enjoy your morning coffee from the screened-in front porch as the sun rises, and savor the evening glow watching the sunset from the private back courtyard. Cool off in the outdoor shower after the beach, and work from home in an amazing outbuilding set up as an office/yoga studio. Rich in charm, history, and heart, this happy home is ready to welcome its next chapter.

ML# :812808   Desirable West Dublin locale - an absolutely ideal location in Greenport Village: only three short blocks to bay beach, four blocks to school and six blocks to the center of all the Greenport action - entertainment, fine and fun restaurants, shops and more! Classic Arts & Crafts, renovated but retaining the charm of the architectural style. Light and bright throughout, open plan that flows from the sunny fully closed-in porch to the living room, dining room and kitchen. Hardwood floors throughout, two bedrooms, full bath with a generous linen closet. Full basement that is only waiting for your imagination. Long driveway and detached garage affords off-street parking or possibly a great playroom! Back yard is deep and offers many outdoor possibilities including room for a pool... Price adjustment...$799, 000

ML# :898986   Welcome to 395 Linnet Street, also known as 806 Linnet Street, Southold – ideally located on the Greenport border.Location truly is everything, and this charming, well-maintained ranch offers a wonderful opportunity for affordable North Fork living. With a desirable open-concept layout, the home is perfectly suited to today’s casual, easygoing lifestyle.The single-level design highlights the expansive backyard, ideal for entertaining, relaxing, or soaking in the peaceful surroundings. Inside, you’ll find 3 bedrooms and 2 full baths on the main floor, updated eat-in kitchen, additional two bedrooms and two bathrooms in a fully finished basement with an outside entrance (OSE), providing flexible additional living space – perfect for larger or extended families, guest quarters, or recreation.Enjoy proximity to bay beaches, local parks, the historic Greenport waterfront village, LIRR, Hampton Jitney, and all the charm, vineyards, Restaurants, and coastal beauty the North Fork is known for.