Newly renovated 1 bedroom apartment short distance from Historical Greenport Village. Freshly painted, new floors, new bathroom with walk-in shower, new washer/dryer, new...

Discover your perfect winter retreat at 317 South Street, Greenport. This delightful 4-bedroom, 1.5-bathroom home blends timeless charm with modern comfort, making it an ...

Super Charming One-Bedroom Cottage on a Desirable Corner Lot, Surrounded by Mature Landscaping and Lush Shrubbery. The Spacious Deck, Brick Patio, and Beautifully Landsca...

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

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...

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

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, ...

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...

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...

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...

Available for $450 per night two week minimum, utility reimbursement. Private Soundfront Wooded Classic post and beam chalet. You will be delighted to see how close you...

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...

This Completely Renovated One-Of-A-Kind Historic Religious Structure was built in 1879. Stylish And Close To Everything In Greenport. Soaring Cathedral Ceilings, Mesmeriz...

GREENPORT WATERFRONT CONDO . Enjoy your life in this well- appointed Bayfront 2 bedroom, 2 bath condo with stunning views of Shelter Island and Greenport Harbor. Ameniti...

2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. Experience North Fork summer living in this newly constructed gem! Nestled in the...

Charming, beach-inspired Greenport home offering easy single-level living just blocks from a beautiful Bay beach and a marina with two waterfront restaurants. Recently pa...