$45,000
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
4,000 sq ft waterfront family home on 3 acres. Plenty of space for the whole family! Our home maintains the traditional charm of a late 19th century farmhouse. If you love vintage houses with an elegant, boho feel, a huge porch to gather with friends...
$34,650
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
Shelter Island PreserveBeautiful Shelter Island Getaway on over an acre, minutes from the ferry!4BR/3BA + an additional sleeping space, private heated pool, outdoor shower, BBQ, total privacy, surrounded by natureWelcome to your perfect S...
$31,710
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
Located in beautiful Hay Beach, this home has four bedrooms and three full bathrooms. The main bedroom has a king bed and a full bathroom with a private entry to the outdoor deck, pool and shower. Bedroom two has two twins, bedroom three has one twin...
$39,000
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
This brand new modern home offers everything you could ask for from a summer retreat in Greenport. Two story height great room with gas fireplace, a seamless layout with bonus room that includes shuffleboard, ping pong and pool table. Large balcony w...
$17,640
Available: Right Now
Listed: 30/06/2024
Town of Shelter Island, NY, 11964
Great location. Situated on 3/4 acre. Walk to Sunset/Crescent beach, ferry, restaurants, shops less than 1 mile. Ice cream parlor and public golf course across the street. 3 Bedrooms, (1 King Bed, 1 Queen Bed, 2 Twin Beds) Air conditioned. 2 bathroom...
$30,540
Available: Right Now
Listed: 30/06/2024
Town of Southold, NY, 11944
Enchanted home with beautiful bay views. This house has it all. Modern updates with old-world charm. Gorgeous chefs kitchen, hardwood floors throughout, stone and marble baths. Located in the center of Greenport, Walk to town. Lovely renovations thro...
$15,270
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedroom, 2 bath home ready to enjoy, especially for a summer getaway or a cozy holiday retreat. It's a 3 block walk into town and a sho...
$14,190
Available: Right Now
Listed: 30/06/2024
Town of Shelter Island, NY, 11964
Modern appliances, marble floors and working fireplace. Creek at the end of private road. Front and back patios. AC in all bedrooms. Close to town, beaches, restaurants, the marina and ferry. Close to paddle boarding, golf, mini g...
$23,970
Available: Right Now
Listed: 25/06/2024
Town of Shelter Island, NY, 11964
Light-filled retreat with 5 sliding glass doors between indoor/outdoor space with heated poolLocated in landscaped setting on pastoral Shelter Island, enjoy the island lifestyle at this new, completely gut renovated, mid-20th century home with mo...
$22,140
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
Coastal Vibes: Home with waterviews, short distance from a secluded beach on Pipes Cove overlooking Shelter Island. Beach/ water access is a 0.4mile walk. The bay is across the street for views. Home features 4 bedrooms and 2 full bathrooms (plus out...
$27,300
Available: Right Now
Listed: 30/06/2024
Town of Southold, NY, 11944
Newly renovated modern farmhouse with the perfect blend of style & comfort. Bask in the serenity of our fully equipped 600 sq ft deck and outdoor oasis (includes plenty of comfy seating, dining, Weber Genesis II grill, fire pit table, and so much mor...
$44,370
Available: Right Now
Listed: 30/06/2024
Town of Southold, NY, 11944
Welcome to Villa Sonore. A gorgeous beachfront home in Greenport located right on the LI Sound. Walk to restaurants and bars at the Soundview. Bike to North Fork wineries, breweries, farms and town. Or just relax on the enclosed porch or back deck an...
$40,500
Available: Right Now
Listed: 24/06/2024
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 ...
$12,000
Available: Right Now
Listed: 30/06/2024
Shelter Island, NY
Sleeps 4 adults (max) or total of 6 with kids.Perfect family getaway.Shelter Island Rental License #: 2023-V-0018Weekly and Monthly Discounts for Winter Rentals!Stay at our newly renovated, light filled home! In the warmer months loun...
$13,170
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
Renovated cape-style home with central ACLiving room w55" Smart TV + sound systemSunny, large den with w65" Smart TV + sound systemOpen indoor dining area off full kitchenLarge, screened porch with comfortable seati...
$22,800
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
3 bedroom with deeded beach rights and partial water view. 5 minute walk to the beach and short drive to the heart of the village. Vineyards, farms, and other activities are all within a short distance.House is situated on nearly an acre of p...
$24,870
Available: Right Now
Listed: 30/06/2024
Town of Shelter Island, NY, 11964
*** 2024 update please read *** We are offering : Monthly or md-ld only . Prices are listed as monthly rates for the periods above .Lush, private 2 acres with heated gunite pool and gorgeous views of the ...
$17,820
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport Village . Walk to town and enjoy the amazing restaurants and shopping that Greenport has offer. This custom Victorian Farmhouse has...
$44,790
Available: Right Now
Listed: 30/06/2024
Town of Shelter Island, NY, 11964
Please note that a reservation for this property needs to be approved before it is confirmed.Shelter Island SereneChic and renovated beach house in a Shelter Island waterfront community, Menantic Creek access, Bluestone patio, oversized gunit...
$30,000
Available: Right Now
Listed: 29/06/2024
Town of Southold, NY, 11944
High on a bluff overlooking the Sound, this amazing Sound front home has been completely renovated with a chef's gourmet kitchen (fully equipped), bright open living room, panoramic water views from every room. 3 Bedrooms, 2 bathrooms and a huge deck...
$25,890
Available: Right Now
Listed: 30/06/2024
Town of Southold, NY, 11944
*30 day minimum rental*Newly renovated modern farmhouse on a spacious property with a large heated saltwater pool and plenty of privacy in the large backyard. All new designer quality furniture throughout the entire house, new Sealy Posturpedic m...
$21,000
Available: Right Now
Listed: 25/06/2024
Shelter Island, NY
Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated summer home across a private beach with large windows, and a sizable garden. The property is two-story with five bedrooms, three b...