424 2nd St Greenport, NY 11944

Set in the heart of the historic district, this c.1890 Greenport Village gem boasts 3 bedrooms, 2.5 baths plus a detached studio apartment. It merges many distinctive original details with thoughtful modern updates. A beautifully planted enclosed rear garden with deck and patio, perfect for relaxing and entertaining, leads to a renovated barn which features a 2-car garage and the spacious studio

Marianne Collins Brown Harris Stevens (Mattituck)

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

Kenneth Poliwoda Douglas Elliman Real Estate

Incredible investment opportunity to own #1 grossing LEGAL short term Airbnb in Greenport Village. Legally permitted - $220k annually. FULLY TURNKEY from furnishings, bedding / linens, towels, to all kitchen ware, even the artwork Maintenance team including house cleaner, pool care and landscaper are at your disposal. 2 minute walk into town - best location in Greenport, across from LIRR

Josh Shenkle EAST END ALLIANCE REAL ESTATE AND DEVELOPMENT LLC

This is more than a renovation—it's a revival of Greenport’s heritage. Originally built in the early 1900s, this farmhouse has been thoughtfully reimagined in 2024 with a full-scale, design-forward renovation that honors its storied past while embracing modern luxury.Featuring 4 bedrooms and 2.5 baths, every inch of this home has been meticulously updated with custom finishes, high-end

Erica Kelly Daniel Gale Sothebys Intl Rlty

This beautiful custom built 2 story home is located minutes from a deeded beach and downtown Greenport with shops, wineries, boating, and golf. This classic style home blends style and comfort. Features include first floor primary bedroom with its own full bathroom and walk in closet, chef's style eat in kitchen with sub zero fridge, Jenn Air oven, and center island, wide plank flooring, living

Chris Bagshaw Bagshaw Real Estate L.L.C

You're looking for a home that truly understands the art of entertaining, and this substantial post-modern residence delivers on every front. From the moment you go inside, you'll be struck by the sheer spaciousness designed to accommodate your grandest gatherings. Imagine the possibilities with five generously sized bedrooms and three well-appointed baths, ensuring ample room for overnight

Donielle Cardinale Daniel Gale Sothebys Intl Rlty

This one-of-a-kind, mid-century modern was designed by renowned architect Claude Samton. Named "Winged Weekend Flight", a wood hewn escape from city ways. When you enter, you will leave your worries behind. Incredible light and gorgeous landscape envelop this 3 bedroom, 1.5 bath sanctuary. Gunite pool with an automatic cover, Ipe decking and beach rights to a gorgeous sound front beach

Sheri Winter Parker Corcoran

Live your best life in this spectacular 5 bedroom bayfront home. Breathtaking panoramic water views from Shelter Island throughout Greenport Harbor to Pipes Cove, you will be able to sit on your private beach and watch all the activity of the Peconic Bay. This beachfront home offers a first floor bedroom en-suite, enclosed sunporch, open floor plan across the living room with wood burning

Kenneth Poliwoda Douglas Elliman Real Estate

Ideally located just minutes from the heart of historic Greenport, this beautifully crafted home offers the perfect blend of coastal elegance and modern comfort. Enjoy access to the serene shores of Peconic Bay where tranquil waters and scenic views invite daily relaxation. Entertain and impress your guests from the bricked patio, and heated saltwater pool. Professional, lush landscaped grounds

Sheila Izzo Century 21 Albertson Realty