Updated, Clean and Tidy Second Floor One Bedroom Apartment for Year-Round Rental. See floor plan in photos.

Discover the charm of this beautifully maintained 2-bedroom, 1-bath home located in the heart of Greenport, NY. Perfect for year-round living, this cozy residence offers ...

August still available! Summer on the North Fork starts here. Welcome to 185 Inlet Lane, Greenport, a spacious 6-bedroom, 4.5-bath coastal retreat designed for entertaini...

2026 Rates are as follows: August 1-15 $20,000 Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore t...

Spacious 2nd Floor 2 Bedroom/2 Bathroom Greenport Village Apartment with Large Covered Deck. Eat in Kitchen with Dishwasher. Private Laundry Room. Central Aircondition...

* low-maintenance North Fork lifestyle, * weekend retreat, * turnkey without renovation headaches, * walkability, * lock-and-leave second home, * income potential, * simp...

Escape the ordinary this summer at 306 6th Street, a home that truly possesses the soul of an artist. Perfectly perched just blocks from everything that makes a getaway s...

Escape To The Heart Of The North Fork In This Beautiful Rental Home Located In Sought-After Greenport. This Charming 3-Bedroom, 2-Bath 2600 Sq Ft Home Offers The Perfect ...

Spend the summer on the Long Island Sound in this stylish 3 bedroom, 2 bath home with a waterside pool and panoramic views. An open floor plan, modern finishes, and seaml...

Charming Greenport Village renovated 1935 Sears Kit House offering 3 bedrooms and 1.5 bathrooms. Ideally located less than half a mile from Greenport’s vibrant downtown, ...

HAMPTONS-STYLE LUXURY WATERFRONT RENTAL — Experience summer on the North Fork in a rare, one-of-a-kind waterfront residence in coveted Stirling Cove—where every room is f...

Beautifully Renovated Greenport Village Farmhouse with Bay Beaches, NYC Transportation, Village Shops and A Marina Nearby. Summer 2026 - July $14,000; August to Labor Da...

2026 NO LONGER AVAILABLE; 2027 RATES COMING SOON This substantial post-modern residence offers the perfect North Fork retreat for those seeking space, comfort, and effort...

Charming whole-house rental in Greenport Village’s coveted West Dublin neighborhood, with a classic bay beach just at the end of the block. The home features lovely furni...

Luxurious Modern Home with Heated Inground Pool in Private Community with a Memorable Community Only Bay Beach Just 3 Blocks Away. Short Distance to Golf and Greenport Vi...

Immaculate Greenport rental with saltwater pool! Conveniently located while also ideally set in a quiet enclave, this home is just a stone's throw to a sandy Bay side bea...

SUMMER RENTAL! BOAT SLIP: Perched above the water with expansive views of Greenport Harbor and Stirling Basin, this unit offers modern luxury on one of Greenport Village...

Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticu...

Introducing Maple Lane — an elegant summer retreat for refined coastal living. Ideally position just moments from the beach enjoy sun-filled days with views across to S...

Brand-new, beautifully designed home with an in-ground pool and finished basement. This exceptional lease opportunity, set within a private beach community, offers a newl...

Advertised price $7000 for 14 nights plus $300/wk utility reimbursement. Private Soundfront Wooded Classic post and beam chalet Short walk to the bluff on the Sound. Adi...

Available year-round rental in Greenport Village. Beautifully updated second floor furnished apartment is ready for you to move in. Located in the heart of Greenport Vil...

Enjoy a few months nestled in the heart of Greenport in a stunning, gated waterfront condo that offers a tranquil escape from the hustle and bustle. With 3 spacious bedro...

Welcome to 485 Sutton Place, Greenport – a newly renovated gem that effortlessly combines modern luxury with timeless charm. Every detail of this stunning home has been t...

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design wi...

Greenport-Immaculate and spacious home. A welcoming front porch leads to the sunny Living room and dining room. A fully equipped gourmet kitchen with Thermador appliances...

Your Fabulous Beach House Vacation! 2 Week Rentals or Monthly! Spacious summer house in the coveted Peconic Bay Estates private beach community on the Bay. A darling hidd...

2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound...

Welcome to your very own pied-a-terre cottage nestled on the world renowned grounds of Harbor Knoll guesthouse. Bask in this waterfront, private and secluded oasis of ca...

Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor p...