$49,200
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Bring the whole family to this great place with lots of room for indoor and outdoor activities! Enjoy an entire Greenport home to yourselves. You have access to all rooms on the first and second floors, an enclosed back yard with a partially cove...
$29,850
Available: Right Now
Listed: 10/05/2024
Town of Southold, NY, 11944
Bachelorette, weddings and big party escape.Go fishing, boating, hiking, golfing, antique shopping etcwalk to town, walk to beach,walk to vineyard, walk to restaurantsEnjoy Greenport, named by Forbes magazine one of the 11 prettiest t...
$8,400
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
North Fork living doesn’t get better than this. Enter to stunning waterfront views from every corner of this unique, light-filled, freestanding corner unit, just a short walk from historic Greenport’s shops, restaurants, and waterfront.Experience...
$85,000
Available: Right Now
Listed: 09/05/2024
23 West Neck Road, Shelter Island, Suffolk County, NY 11964, USA
Rental Registration #20L-0086This farmhouse features a wrap around porch, free form pool and large lawn and open floor plan. With an open layout, entertaining guests is easy. The kitchen features granite countertops, stainless steel appliances and br...
$72,000
Available: Right Now
Listed: 09/05/2024
53 North Cartwright Road, Shelter Island, Suffolk County, NY 11964, USA
This wonderful, open and renovated 4 bedroom, 2.5 bath sits on just shy of an acre and features open spaces, library and media room. Master bedroom on the 2nd floor features an en-suite bath and 3 additional bedrooms and bath. House sits on a lovely ...
$18,000
Available: Right Now
Listed: 10/05/2024
Town of Southold, NY, 11944
Beautiful updated historic home in the village of Greenport. Central AC, newly renovated kitchens and bathrooms, large fenced in yard, patio with bbq, outdoor shower, fire pit. Bike to nearby vineyards and beaches and walk to restaurants, stores and ...
$22,000
Available: Right Now
Listed: 09/05/2024
6 Summerfield Place, Shelter Island Heights, Suffolk County, NY 11965, USA
Charming 6 bedroom Victorian on Shelter Island Sound. Eat-in-kitchen, dining room, master bedroom, and front parlor opening to waterside rocking chair porch. Four Craftsman Victorian bedrooms on second floor, one with a waterfront screened porch. Nea...
$40,000
Available: Right Now
Listed: 09/05/2024
2 Sylvan Place, Shelter Island Heights, Suffolk County, NY 11965, USA
Beautifully restored iconic Shelter Island Heights Victorian with lovely views of Dering Harbor, Chase Creek, rolling green lawns and a small treed park. Situated within convenient proximity to all that Shelter Island Heights offers with shops, resta...
$29,670
Available: Right Now
Listed: 06/05/2024
Town of Shelter Island, NY, 11964
Score Big at our fabulous Hamptons Cottage where work meets play in style! Settle into this charming 1700’s cottage nestled on 7 private acres of lush greenery adorned with majestic trees-your very own oasis!Excellent Wifi: Say goodbye to buf...
$52,000
Available: Right Now
Listed: 09/05/2024
6 Cozy Lane, Shelter Island Heights, Suffolk County, NY 11965, USA
Located within close proximity to sandy beaches and town landing, this cottage has a spacious living room which has a fireplace and bay windows that look out onto tall white pines and lilies of the valley. The kitchen has custom cabinetry, appliances...
$94,230
Available: Right Now
Listed: 10/05/2024
Shelter Island, NY
Sunset BeachElevated Views Over Shelter Island Sound, Wraparound Deck Overlooking Beach, High-End Amenities, Access to sandy dock6BR/5.5BA,Cinematic Media Room, Fitness Room, 2 Docks, Indoor Pool & SpaTheres ordinary, and theres Sunset Be...
$35,000
Available: Right Now
Listed: 09/05/2024
3 Primrose Place, Shelter Island Heights, Suffolk County, NY 11965, USA
Located near Coecles Harbor, Gardiners Bay Country Club golf course, and several island beaches, this new home on a wooded acre enjoys a spacious open design with vaulted ceilings. Featuring a living room with a stone fireplace, dining area, stylish ...
$72,000
$72,000
Available: Right Now
Listed: 09/05/2024
15 Stearns Point Road, Shelter Island Heights, Suffolk County, NY 11965, USA
Located within close proximity to popular Sunset Beach, golf, tennis and Perlman Music Camp in desirable resort area, this hand-crafted Scandinavian style farmhouse with summer guest cottage and barn with loft on 1.5 acres was thoughtfully built and ...
$42,500
Available: Right Now
Listed: 09/05/2024
76 North Cartwright Road, Shelter Island, Suffolk County, NY 11964, USA
Perfect combination of new and old. Delightful great room/dining room/kitchen with fireplace and French doors to back deck, sitting room with fireplace. The second story has fabulous deck and walkway with a peek at Coecles Harbor, large master bedroo...
$80,000
Available: Right Now
Listed: 09/05/2024
70 South Ferry Road, Shelter Island, Suffolk County, NY 11964, USA
Stunning renovation of this ultra charming c. 1822 historic Shelter Island farmhouse. Completely redone for every modern convenience while maintaining the integrity of the original dwelling with great attention to period and detail. This beautifully ...
$6,870
Available: Right Now
Listed: 10/05/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$20,250
Available: Right Now
Listed: 07/05/2024
Town of Shelter Island, NY, 11964
Shelter Island is a unique place with incredible natural landscapes and gorgeous sunsets!Once you get off the ferry, drive to the end of a private road to find your oasis on a full acre of land where you will relax and enjoy the sun drenched back...
$16,500
Available: Right Now
Listed: 09/05/2024
6 Conrad Road, Shelter Island, Suffolk County, NY 11964, USA
RR# 19L-0061This grand compound bordering parkland is spectacular. The main house spans 4700 sf holds 5 bedrooms, 5.5 bathrooms, an open and spacious living room with fireplace, formal dining room, and a gourmet kitchen and top of the line appliances...
$15,750
Available: Right Now
Listed: 10/05/2024
Town of Southold, NY, 11944
Enjoy this beautifully renovated first floor “Captains House” apartment in the heart of Greenport Village. Harbor Views! Walk to town.This 2 bedroom, 2 full bathroom home is bright with sunshine, has soaring ceilings and hard wood floors, easy to...
$20,000
Available: Right Now
Listed: 09/05/2024
11 Emerson Lane, Shelter Island, Suffolk County, NY 11964, USA
This wonderful cottage on bucolic Shelter Island has been recently renovated and is now available for summer rental. With spacious kitchen with dining table, island seating and breakfast patio outdoors. Large bright living room that looks out to back...
$35,730
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
An outdoor oasis is one element of this extraordinary property. This one of a kind 5 bedroom, 3.5 bath residence is the perfect home to make special memories this season. The perfect rental with one of the most extraordinary pool and garden areas on ...
$12,750
Available: Right Now
Listed: 04/05/2024
Town of Shelter Island, NY, 11964
Relax on Shelter Island. Enjoy a central location close to town and amenities within a short bike ride of Wades Beach, golf, tennis, and local oysters. Under 2 miles to Sunset Beach, The Chequit, and Leon restaurants, Marie Eiffel market, Sylvester M...