Greenport NY Real Estate & Homes for Rent

Summer 2024 Rates: June 27-July 11 $15K, Sept4-Oct4 $5K/week: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

Enjoy a Quintessential North Fork Summer at this Chic Cape at Pipes Neck Cove. Located Just Outside Greenport Village on a Quite Road Off the Beaten Path. The Home Boasts Beautiful Waterviews of the Cove from Nearly Every Window. The Enchanting Bay Beach is just a Stone's Throw from the Home and is Truly One of the Most Special Locations on the North Fork. The Vast and Nearly Private Beach Overlooks Greenport Village and has Expansive Views of Shelter Island. The Cove is the Perfect Spot to Fish, or Explore by Kayak, Canoe or Paddleboard. A Mooring is Also Available if Interested. The Home Itself has an Open Yet Cozy Layout for Living and Dining. The Interior has been Thoughtfully Decorated to Create a Warm and Welcoming Atmosphere. Great For Entertaining or Lounging and Just Taking in the View. The Spacious Bedrooms are 2 Up and 2 Down to Accommodate All with a Full Bath on each Floor. The Vibrant Village of Greenport is Moments Away Where You will Explore Quaint Shops, Great Dining or Possibly a Ride on the Carousel! Make this Your Home Away from Home this Summer Season. You are Guaranteed to Fall in Love. Rental Permit #0957

Just a ferry ride from Sag Harbor and the Hampton's, take in expansive waterfront views of the bay and Greenport harbor from the second floor balcony in this renovated open concept waterfront condo located in the private Stirling Cove condominium association. This light filled townhouse offers a private beach, 60' x 30' heated pool overlooking the bay, two tennis courts, private parking and is two blocks from the heart of Greenport Village and Mitchel Park. Perfect for enjoying the renowned restaurants, shops, parks, marinas and other attractions Greenport Village has to offer without the hassle of searching for a two hour parking spot. Appliances included are a washer/dryer, dishwasher, stove, microwave, refrigerator. Rental Permit # 23317

A new addition this fall, a 20 x 40 heated in-ground pool in private yard, this fully renovated Greenport home has been stylishly decorated and features a large, eat-in kitchen, expansive living room, 3 bedrooms with two ensuite full bathrooms and a third full standalone bathroom. The residence has a large side yard and patio on a 1/3 of an acre and is third of a mile to the heart of Greenport Village as well as nearby beaches, marinas, parks, wineries and restaurants. Rental Permit # 0200

Winter/Off Season and Summer Furnished House Rental. 4 Bedroom/2 Bathroom Cape Close to Greenport Village. Formal Dining Room, Separate Den with TV, Screened Porch with Large Dining Table and Summer Kitchen Set Up. Nicely Manicured Lawn for Enjoyment. October 2023 to May 2024 $3,500 Per Month; SUMMER 2024 - June $9,000; June 28 to July 12 $5,600; Summer Weekly $2,800 (with two week minimum). Permit #0701.

Rental #0843

Newly renovated farmhouse located in the heart of Greenport village. This 3 bedroom 2 bath first floor apartment is steps to shops, restaurants & historic waterfront. Enjoy summer days in the potager garden and nights grilling the daily catch. The apt features a sunny open kitchen with an open floor plan, a master bedroom with en suite bath, and two additional bedrooms with ample light and a cozy feel.

This beautiful waterfront cottage offers panoramic water views and breath-taking sunsets! The home is newly furnished and updated, ready for you to stay the summer months. Relax on the water side deck and enjoy one of the North Forks most beautiful protected tidal saltwater ponds. There is direct water access from the back yard to paddle the day away. Greenport Village shops and restaurants are just 2 miles away. This home is located between bay and sound beaches, farm fresh vegetable stands and wineries too! Available: 2024: July $15,000 August $15,000 Southold Town Rental Permit #0511

Greenport Village West Dublin architectural home is available for you to enjoy! This wonderful home includes 3 bedrooms, 2 full baths, formal dining room, beautifully designed open floor with impeccable detail. The backyard setting is fabulous with patio, specimen plantings, grill and firepit. Perfect location between the 5th Street beach, villages shops and downtown restaurants. Easy access to the train and jitney bus transportation. Available 2024 Rates: June $20,000, July $30,000, August- Labor Day $35,000 Year round lease available for $4500 per month. Greenport Village Rental Permit #21-056

Tucked Away Along Sterling Harbor in Greenport's Historic District On the Village's Most Desired Street. This Lovely 3 BR, 2 BA Cottage Is Only A Block From the Maritime Village With Its Many Restaurants, Cafes, Shops, Mitchell Park & Carousel. Enjoy Your Morning Coffee & Evening Cocktails On The Waterview Deck. Close to All Transportation, Beaches & Wineries.

Excellent North Fork vacation location! Tastefully appointed 3BR/4 BA Colonial in pristine, like new condition. Every amenity including a heated, saltwater pool plus 3 living/media rooms. Lovely, quiet neighborhood with a sandy Bay beach & gorgeous Sound beach just minutes away. Nearby CSA farmstands & seafood markets for enjoying farm to table, poolside dining. Renowned restaurants and Greenport's vibrant downtown only 5 minutes away. [Rental permit #0384 Exp. 2/9/2025].

Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views of the cove and bay. Featuring newly renovated, spacious kitchen, dining room, elegant living room with wood burning fireplace, water view deck, and powder room. Second floor has master bedroom suite with expanded, renovated bath and private water view balcony. A guest room with private bath and laundry complete the floor plan. Unit comes with a private boat slip in the protected basin with easy access to the cove and bay. Complex offers heated in-ground pool, tennis courts, private beach - all just a short walk to Greenport Village restaurants, shopping, and grocery. Near Islands End golf course and access to all that the North Fork has to offer. Full-time on-site management. Jan $5,000; Feb $5,000; March $5,000; Apr $6,500; May $11,000, June $15,000; July $22,000; August $22,000; Sept $15,000; Oct $10,000; Nov $7,000; Dec $7,000. Permit# 21-048.

Newly Renovated Unit W/Spectacular Views Of Bay, Beach & SI Beyond. 2 Bed/ 2 Bath. Styled Elegantly. Open Plan W/ Views From Every Window. Waterfront Balcony On Beach. Complex has a Waterfront Pool, Tennis & Pickle Ball Court & Over 200 Ft of Bay Beach. Rental Includes a Boat Slip in Marina. In Heart Of Village. Close To Restaurants, Transportation, Ferry & Shops. (Southold Town Rental Permit #21-063) June $13500; July $18500; Aug-LD $23000.