North Haven NY Real Estate & Homes for Rent

Discover the ultimate summer rental at 49 Whooping Hollow Road, a stunningly transformed Post Modern nestled between the vibrant villages of East Hampton and Sag Harbor. This exceptional property is situated on almost half an acre, offering 2200 +/-sq. ft. of light-filled living space with a captivating beach vibe that will leave you feeling right at home. The open floor plan features a modern kitchen, dining area and a large living room that flows effortlessly, creating a perfect gathering spot for friends and family. The Anderson sliding doors lead out to an expansive deck, perfect for outdoor entertaining, while the first-floor primary suite, two guest rooms, and additional sleeping room upstairs with a private balcony create ample space for everyone. The lower level offers even more space with a full bath, laundry room, two-car garage, and entertainment area that leads out to a heated pool and spacious patios. You'll love the stylish decor and the hardwood flooring throughout, as well as the central air conditioning that keeps the home cool and comfortable on even the warmest days. But that's not all! The private outdoor space is perfect for relaxation and unwinding after a day at the beach, while the entry foyer adds a touch of sophistication to this already impressive property. So why wait? Experience the ultimate summer lifestyle at 49 Whooping Hollow Road, where beach vibes and a great location come together to create an unforgettable rental experience.

Permit 681 .Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. Make Memories In This Wonderful Summer Rental!

Rental Permit# 200858 - Five bedrooms, four baths postmodern home offers kitchen with stainless steel appliances, breakfast nook, dining area, living room with fireplace, and den/TV area with fireplace, heated pool and har-tru tennis court.

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

Welcome to beautiful 112 Laurel Valley Drive, your destination to enjoy all that Sag Harbor has to offer. This is also a perfect launch pad to explore Southampton, Bridgehampton, some of the worlds best ocean and bay beaches, shops and the restaurants that The Hamptons are known for. Majestically set upon a hill, this home provides a private back yard with a heated in-ground pool that is a perfect setting for entertaining. The open floor plan is both expansive and inviting. There are four large bedrooms and three full bathrooms. Primary en-suite bedroom is on the first floor. Make 112 Laurel Valley Drive your destination for a memorable Sag Harbor summer.

Welcome to 1355 Watersedge Way a delightful Bayfront home located on Little Peconic Bay in Southold. Inside you have a spacious living room with a smart TV and a wall of sliding glass doors the lead out to the waterside deck, eat in kitchen, two bedrooms and one bathroom. on the lower level there is a family room with wet bar and access to the yard and outdoor shower, one bedroom, a full bath, and washer and dryer. The house is located next to a nature preserve with 300 ft. of beach providing easy access to the water/bay and plenty of privacy. Enjoy the spectacular views of the water and sunsets! MD TO LD $50k, June$12k, July $23K; August 1 to LD $24K, off season $7k for 30 days. House is available from May to November with a minimum of four weeks that does not need to align with the calendar month. RP# 0929

A welcoming first floor with beautiful natural light from the giant sliders welcoming you to the deck with a large and heated pool. Enjoy the privacy protected by lush green trees and bring relaxation to the next level. Upstairs you will find two good sized bedrooms with a shared bathroom. With the outdoor oasis, you likely won't be spending too much time indoors, but if you choose to you will be as comfortable as ever. Washer and dryer are available in the basement so you never have to leave this gorgeous set up!

Private 7+ acre estate, 7000sf post-modern 5 bedrooms, 5 baths, great room with lovely fireplace, formal dining, den, sunroom, casual dining, modern kitchen, lavish master with lounge or exercise room, French doors open to private deck with beautiful outdoor seating. Freshly renovated, chic new furnishings, fixtures, flooring, linens, kitchen appliances, and a full finished lower level with pool table, lounge area with bar & sink, tv/theatre room, full bath, private office with separate entry opens to tiled patio with grill & fireplace. Lushly landscaped, fenced heated Gunite pool, pool house with yoga room/gym equipment, 3 car garage, gardens, walking trails & pond, side & rear brick patios. A rare offering of nature, luxury, privacy, and location!

2024 RATES: JUNE $12,500, JULY $16,000.00 AUGUST $17,000 MD-LD $44,500. Victorian classic in the heart of Greenport Village. Centrally located seasonal offering. This charming and updated victorian home provides convenient access to all Greenport Village has to offer. You will enjoy water-views from almost every room, beach access right across the street, walking distance to all restaurant and shops. The interior is incredibly well appointed with a formal living room, media room, formal dining room, updated kitchen, bedroom, full bathroom and laundry on the main level. The 3 additional bedrooms on the second floor are all ensuite. Additionally, there is a large open air porch looking directly out to Greenport Harbor, along with an enclosed porch off of the media room. Jump on this fantastic offering before it's too late.

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

Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. Available October 24 - April 2025 Or July 2025. Exit Clean, Utility & Security Deposit Required. Leased For July 24

Light and airy modern home nestled in amongst the trees on a beautiful private property. High ceilings and windowed walls abound in this gorgeous 3 bedroom 2 1/2 bath home. Main floor features expansive living space, vaulted ceilings, open dining room and updated kitchen. All rooms are generously sized, newly furnished (designer chic) and have the comforts of home. The beautiful park-like property (1+acres) is surrounded by tall trees and the sounds of birds singing. Enjoy your coffee on the sun filled front balcony and or grill out on the large back deck. Play all day in the large in ground heated pool, walk to the bay beach or take a hike on nature trails accessed right from the cul-de-sac at the end of the road. Separate 2 car garage, outdoor shower and other perks. This home is ideally situated between Sag Harbor & Southampton villages and very close to beaches, farms, nature preserves and much more. A stunning, peaceful retreat in any season.

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

Privately situated in the Northwest Woods of East Hampton on two acres sits this perfectly designed and decorated 3 Bedroom and 3.5 bath property. Entering this dramatic you are greeted by a generous foyer and renovated half bathroom. As you proceed further, the heart of this home is its expansive living area, where the kitchen, dining, and living spaces meld seamlessly, promoting a sense of togetherness and connectivity. In addition, there is a beautiful den/sunroom area that bathes in natural light on the first floor as well as two guest bedrooms with a shared bathroom. Proceeding to the second floor there is a large primary bedroom with oversized bathroom and an outdoor roof deck that is perfect for morning coffee. Also on the second floor there is a small room that can be used for an office or additional guest sleeping. Outside you are greeted by the large heated pool and expansive deck area with outdoor kitchen which is perfectly designed for summer living and enjoyment. In addition to expansive outdoor living area, there is basketball court not only provides a recreational outlet but also adds a dynamic and active element to the property. Both inside and outside kitchens add elements of luxury and versatility, catering to various preferences and lifestyles. Whether it's a summer barbecue by the pool or a cozy indoor gathering during colder months, the home seems well-equipped for diverse entertaining options. If you are looking for a newly decorated, pristine rental that is perfect for the summer, look no further. Come and enjoy

Minutes to the beach is this fantastic Contemporary with some water views and fall in love! Located in a desirable waterfront bay beach community and completely renovated with great taste, a modern feel and all new furniture decorated from a well-known interior designer. Sited on .80 acre, this bright home filled with light offers 4 bedrooms and 4.5 baths, an open floor plan, living room with cathedral ceilings and wood burning fireplace. Primary suite on the first floor with a beautiful marble bathroom. Spacious kitchen with stainless steel appliances and stone countertops, 2 dishwashers and a wine cooler. Powder room and a mud room leading to the 2 car garage completes the first floor. The second floor offers a den with an open view to the living room, 2 additional guest bedrooms and 2 marble baths. Finished lower level with living area with TV and games, as well as a bar, bedroom, full bath, laundry office and a small gym. Hardwood floors throughout the house. Step out and enjoy the stunning outdoor space that has it all with an oversized bluestone patio with an outdoor kitchen, lounge area, fabulous heated saltwater pool, outdoor fire pit, outdoor shower and an oversized hot tub. This quiet neighborhood has a community bay beach access and 2 community all weather tennis courts, providing the perfect living in the Hamptons!

This elegant one level home features 4 bedrooms and 4 baths with new designer furnishings. The high vaulted ceiling living room is full of light and offers a wood burning fireplace with an open floor plan to a gourmet kitchen with easy flow. French doors open to a generous deck for entertaining. The stunning, substantial backyard backs-up to a reserve offering privacy with a great heated pool and outdoor shower. This crisp and spacious home is located on a private cul-du-sac with a quiet neighborhood and prime location in the middle of Bridgehampton's horse country, a well-known vineyard nearby and a short distance to village and ocean beaches. This is also an equestrian's delight since the home is located only 2.1 miles from the grounds of the Hampton Classic Horse Show.

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023

Charming, Furnished 2nd Floor Greenport Village One Bedroom Apartment. Convenient to All. Nice Beach at the End of the Street. Winter 2024 $2,600 Per Month; Summer 2024, Memorial Day to Labor Day $10,000; June $3,500; July $3,500; August to Labor Day $3,500.

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 with sliding doors to back deck, family room with vaulted ceilings also has access to large back deck, there is another den/office, a full bathroom with shower and laundry all on the first floor. The second floor there are two en-suite bedrooms and two additional bedrooms and full bath. Large manicured yard with deck and patio landscaped for privacy. Close to beaches, farm stands, Southold Fish Market, wineries and Greenport Village. Spend this summer in Greenport in this wonderful home. July Rented from July 20-August 3. Available June $15,000/month, June 20-July 20 for $20,000, August 3-LD $20,000, 2 or 3 weeks in July or August $7500/week and Off season $5000/week (2 week Minimum) #0744

HANDS CREEK HARBOR STUNNER RR# 24-335 Renovated from top to bottom, this 3 bedroom/ 2.5 bath contemporary has been meticulously updated. Soaring, bright living room has 15' vaulted ceilings, shiplap paneling, quartz clad fireplace and sliders to the front and back decks. Separate dining room and floor to ceiling glass sunroom offering true indoor/ outdoor living. Newly renovated kitchen with SubZero and Wolff stainless appliances. Primary en suite occupies the rear of the home with sliders to a private deck overlooking the pool and professionally landscaped grounds. Two additional bedrooms with skyights and another full bath complete the first level. The lower level is comfortably finished with a large media room, bar area with wine fridge, beverage center and ice maker, fully equipped gym, powder room and laundry. Ouside, the beautifully landscaped grounds abound with mature plantings, masses of hydrangeas, azaleas and multiple specemin trees allowing for maximum privacy. The spa like pool is gunite, heated, saltwater and has a large sun shelf that can accommodate 4 loungers. Two waterfalls spill from a custom cut stone wall that wraps around the pool and ends with a fire feature. The home is in the coveted Hands Creek Harbor association with a private 2 acre water front parcel with access for kayaks and paddle boards into Three Mile Harbor. A true gem and offered for the first time.

This Victorian home in Greenport Village truly captures the essence of a dream residence. The second-floor apartment boasts a bright and spacious atmosphere, complemented by a welcoming front porch. Private amenities such as a driveway, entrance, and laundry facilities enhance the sense of convenience... recent upgrades including new floors and central air conditioning ensure modern comfort. Bonus: outside shed can be envisioned as a multi-purpose space, a cozy outdoor retreat, a space for hobbies or crafts, or even a small studio for artists or writers seeking inspiration amidst the tranquility of the garden. It's the perfect place to settle in and enjoy all that Greenport has to offer, from its transportation options to its dining and shopping scene. Can be offered lightly furnished or unfurnished -choice is yours. Tenant responsible for electric and oil for heat. Landlord pays water, sewer and household trash. Greenport Rental Permit #22-171.

Chic and Stunning and 2022 renovation complete! Spend your Summer in the Hamptons at 2023's most popular rental. This stylish and light filled home includes 3 levels of finished space, with privacy and also room to gather as a group. Complete with heated gunite pool, an expansive and beautifully landscaped property, tennis and private beach. Centrally located between the Villages of Southampton and Sag Harbor.

Fabulous Water Front .condo.Deep water Dock. Pool Tennis.Vibrant Greenport Town